Petition for Writ of Certiorari — Daviel Salinas-Acevedo, Petitioner v. United States

Supreme Court briefDec 8, 2017

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No. ____-________

IN THE SUPREME COURT OF THE UNITED STATES

DAVIEL SALINAS ACEVEDO,

Petitioner,

v.

UNITED STATES OF AMERICA

Respondent.

On Petition for a Writ of Certiorari to the United States

Court of Appeals for the First Circuit

___________________________________

APPENDIX

___________________________________

22

TABLE OF CONTENTS

Judgment of the First Circuit denying petition for rehearing en

banc. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1

Opinion of the First Circuit denying petition for rehearing en banc

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2

Panel opinion of the First Circuit. . . . . . . . . . . . . .

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United States Court of Appeals

For the First Circuit

No. 13-2072

UNITED STATES OF AMERICA,

Appellee,

v.

DAVIEL SALINAS-ACEVEDO,

Defendant, Appellant.

Before

Howard, Chief Judge,

Torruella, Lynch, Thompson, Kayatta, and Barron, Circuit Judges.

ORDER OF COURT

Entered: July 11, 2017

The petition for rehearing having been denied by the panel of judges who decided the case,

and the petition for rehearing en banc having been submitted to the active judges of this court and a

majority of the judges not having voted that the case be heard en banc, it is ordered that Daviel

Salinas-Acevedo's March 16, 2017 petition for rehearing en banc be denied.

By the Court:

/s/ Margaret Carter, Clerk

cc:

Hon. Carmen Consuelo Cerezo

Frances Rios de Moran, Clerk, United States District Court for the District of Puerto Rico

Ignacio Fernandez-De-Lahongrais

Daviel Salinas-Acevedo

Myriam Yvette Fernandez-Gonzalez

Mariana E. Bauza Almonte

Eric Linden Gibson

Juan Carlos Reyes-Ramos

Robert James Heberle

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United States Court of Appeals

For the First Circuit

No. 13-2072

UNITED STATES OF AMERICA,

Appellee,

v.

DAVIEL SALINAS-ACEVEDO,

Defendant, Appellant.

Before

Torruella, Lipez, and Thompson,

Circuit Judges.

ORDER OF COURT

Entered: July 11, 2017

Daviel Salinas-Acevedo ("Salinas-Acevedo") has filed a petition for a rehearing or

rehearing en banc alleging "the panel decision conflicts with a decision . . . of the court to which

the petition is addressed." Fed. R. App. P. 35(b)(1)(A). Salinas-Acevedo asserts that the panel's

January 13, 2017 decision, affirming the district court's refusal to permit him to make an

entrapment defense, conflicts with our prior holding in United States v. Gendron, where we noted

that "[c]ourts have found a basis for sending the entrapment issue to the jury . . . where government

officials . . . used 'repeated suggestions' which succeeded only when defendant had lost his job and

needed money for his family's food and rent." 18 F.3d 955, 961 (1st Cir. 1994) (quoting United

States v. Kessee, 992 F.2d 1001, 1003 (9th Cir. 1993)). Because our January 13, 2017 decision

does not conflict with Gendron, but instead finds the facts of this case distinguishable such that an

entrapment instruction was not necessary, Salinas-Acevedo's petition for panel rehearing is denied.

In our ruling rejecting Salinas-Acevedo's argument that he was entitled to an entrapment

defense, we first assumed that Salinas-Acevedo properly preserved his entrapment arguments,

affording him the benefit of de novo review. We noted that a defendant seeking to present an

entrapment defense at trial must demonstrate (1) improper inducement and (2) that he was not

already predisposed to commit the crime. See United States v. Sánchez-Berríos, 424 F.3d 76 (1st

Cir. 2005). Salinas-Acevedo's argument relied on a derivative theory of entrapment, where a

middleman's actions can be attributable to the government if:

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(1) a government agent specifically targeted the defendant in order

to induce him to commit illegal conduct; (2) the agent acted through

the middleman after other government attempts at inducing the

defendant had failed; (3) the government agent requested,

encouraged, or instructed the middleman to employ a specified

inducement, which could be found improper, against the targeted

defendant; (4) the agent's actions led the middleman to do what the

government sought, even if the government did not use improper

means to influence the middleman; and (5) as a result of the

middleman's inducement, the targeted defendant in fact engaged in

the illegal conduct.

United States v. Luisi, 482 F.3d 43, 55 (1st Cir. 2007).

We noted that while Salinas-Acevedo met elements (1) and (2), he failed to meet his burden

with regard to element (3) -- namely, demonstrating that the government agent (Camacho)

requested, encouraged, or instructed a middleman (Rullán-Santiago or Méndez-Perez) to employ

a specified improper inducement. Although Salinas-Acevedo was presented with repeated

opportunities to engage in the illegal activity and it is undisputed that he was facing difficult

financial times, we found Camacho's specific instructions not to pressure Salinas-Acevedo, along

with other facts in this case, to be sufficient evidence that Camacho did not instruct the middlemen

to engage in improper inducement.

In denying Salinas-Acevedo's petition for rehearing, we take this moment to further clarify

our holding in this case. "Inducement requires not only giving the defendant the opportunity to

commit the crime but also a 'plus' factor of government overreaching." United States v. GonzálezPérez, 778 F.3d 3, 11 (1st Cir. 2015) (quoting United States v. Guevara, 706 F.3d 38, 46 (1st Cir.

2013)). In González-Pérez, 778 F.3d at 12, another Operation Guard Shack defendant similarly

claimed, as Salinas-Acevedo does here, that he had been targeted because of his difficult financial

situation and had been repeatedly solicited despite his initial resistance. There, we held that the

circumstances did not amount to improper government inducement because the government had

employed "no arm-twisting or undue coercive method." Id. Additionally, we held that the

defendant's circumstances in that case -- he "had various part-time jobs . . . and . . . thought that

the high payment offered by [the government agent] would help him solve his financial situation"

-- was not enough to constitute inducement. Id. Here, we hold that Salinas-Acevedo has similarly

failed to produce any evidence of government overreach or arm-twisting.

Indeed, the record indicates and the parties assert that Salinas-Acevedo was solicited, at

most, a total of three times.1 The first time took place at some point before March 9, 2010. During

a call on March 9, 2010, Rullán-Santiago informed Camacho that at the last minute SalinasAcevedo had decided not to participate in a sham drug deal. Rullán-Santiago told Camacho that

1

The dissent argues that it is "misleading" to say that there were only three solicitation requests.

The dissent would have us speculate as to an infinite number of requests. However, we rely on

the record as well as the parties' representations and decline to speculate where the record is silent.

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Salinas-Acevedo had cited his daughter as the reason he could not participate. Rullán-Santiago

also informed Camacho that in response to Salinas-Acevedo's decision not to participate, RullánSantiago had told Salinas-Acevedo "[l]ook, [sic] is all right, bro" and to "[f]orget it, cool. That's

cool."

The second time that a middleman solicited Salinas-Acevedo to take part in the sham drug

deals presumably occurred after another recorded call. In that call Camacho spoke with MéndezPerez, brought up Salinas-Acevedo, and asked Méndez-Perez what he thought of Salinas-Acevedo.

The call is somewhat confusing, but ends with Camacho asking Méndez-Perez to talk to SalinasAcevedo, and Méndez-Perez indicating that he would go to Salinas-Acevedo's home to talk to him.

Camacho specifically instructed Mendez-Perez not to pressure Salinas-Acevedo, stating that "if he

gives you a lot of crap . . . [t]his isn't compulsory, this is for those who want to and know what it

is."2

The last indication in the record of Camacho instructing a middleman to recruit SalinasAcevedo occurred sometime after March 19, 2010. During a call on that date, Camacho offers

Rullán-Santiago an opportunity to work another sham drug deal. Rullán-Santiago jumps at the

opportunity and Camacho asks him to "get that guy that you tried to find last time." RullánSantiago responded that he would see if Salinas-Acevedo was available, stating "[o]kay, let me

see if, if that dog is around here." Camacho then tells Rullán-Santiago to let him know for sure

whether Salinas-Acevedo would participate because he did not want him to "do the same shitty

thing to me like you did last week" -- when Salinas-Acevedo decided not to participate at the last

minute.

Given these facts, we find the three requests here, over approximately a ten-day period, do

not amount to improper coercion or inducement by the government. Although Salinas-Acevedo

was facing financial difficulties with the impending arrival of a second child, financial distress

alone does not render the repeated presentation of an opportunity to commit a crime improper. See

United States v. Baltas, 236 F.3d 27, 36 (1st Cir. 2001) ("Improper inducement goes beyond

providing an ordinary opportunity to commit a crime. An inducement consists of an 'opportunity'

plus something else -- typically, excessive pressure by the government upon the defendant or the

government's taking advantage of an alternative, non-criminal type of motive." (citations

omitted)). And while we noted in Gendron, 18 F.3d at 961, that repeated suggestions in light of a

defendant's financial straits may merit an entrapment instruction, the facts of this case are

distinguishable.

Unlike the defendant in Kessee, Salinas-Acevedo at no time faced any sudden change in

means and therefore did not suffer from any increased vulnerability that would make the

government's later repeated offers to participate more objectionable. See Kessee, 992 F.2d at 1004

(noting that the "repeated entreaties . . . only became successful when Kessee had lost both his

jobs" and "did not know where he would get the money for rent and food for his family").

2

As noted in our original opinion, Méndez-Perez may have never followed through on his plans

to recruit Salinas-Acevedo as indicated during this call. See United States v. Rivera-Ruperto, 846

F.3d 417, 429 n.8 (1st Cir. 2017). We, however, assume arguendo that this solicitation actually

took place although the record is silent as to what was actually asked of or said to Salinas-Acevedo.

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Moreover, the government agent here expressly instructed at least one middleman (Méndez-Perez)

not to pressure Salinas-Acevedo. And although the second middleman (Rullán-Santiago) was

never given such direct instructions, during the March 19, 2010 call when Camacho suggested that

Rullán-Santiago "get that guy that you tried to find last time" (in reference to Salinas-Acevedo),

Camacho also made clear that he simply wanted Rullán-Santiago to bring an associate to

participate in the deal -- not necessarily Salinas-Acevedo, but someone.

Indeed, Rullán-Santiago understood that if Salinas-Acevedo declined to participate and he

could not get someone else to join, they might postpone the deal. Camacho even made a specific

suggestion that Rullán-Santiago could seek out an alternative participant (if Salinas-Acevedo was

not available), such as another individual "from Maricao, I don't know, the one you had told me

about." Thus, Camacho never instructed Rullán-Santiago to employ inappropriate means to recruit

Salinas-Acevedo, but merely instructed him to provide Salinas-Acevedo with an opportunity -Salinas-Acevedo was free to decline and Camacho was only interested in Rullán-Santiago

recruiting a second corrupt officer to participate. Indeed, this lines up with the overall design of

the sting operation to "hire" corrupt law enforcement officers to provide armed security at the

staged drug deals, and then have those officers recruit others to participate in subsequent deals,

thereby unwittingly assisting the sting in ferreting out additional corrupt officers. The dissent

seems to find it important that Camacho never gave Rullán-Santiago explicit instructions not to

pressure Salinas-Acevedo (like those given to Méndez-Perez); however, the absence of such an

instruction does not establish that the government instructed Rullán-Santiago to employ a specific

improper method of inducement. And Rullán-Santiago was explicitly instructed only to recruit

another corrupt cop, be it Salinas-Acevedo or some other officer. In sum, merely providing the

opportunity to commit a crime, even if repeatedly, does not by itself rise to the level of improper

government overreach. See Baltas, 236 F.3d at 37. We find that there is no evidence of an

improper attempt to persuade Salinas-Acevedo to participate and that the government merely

presented Salinas-Acevedo with an opportunity to commit a crime.

Although we believe the dissent takes several creative liberties in its reading of the record,

drawing conclusions and inferences which are, in our view, unfounded, we briefly address a few

of its concerns.3 As mentioned by the dissent, we are well aware that Salinas-Acevedo only has

to present sufficient evidence that if believed by a rational juror would create a reasonable doubt

that he committed the crime of his own accord. And as mentioned above, such a showing requires

3

The dissent misleadingly contends that the majority makes several "concessions," which we do

not make. Our January 13, 2017 opinion does note that Salinas-Acevedo "backed out" of the first

transaction at the last minute. We still believe this to be true and supported by the record.

However, we acknowledge that the record does not provide any affirmative evidence of SalinasAcevedo's initial agreement to participate after the first request. The record indicates, however,

that Salinas-Acevedo intended to participate in the first transaction until he realized that his

daughter's daycare was closed on the Wednesday when the first transaction was scheduled and he

had no one to watch her ("[Salinas-Acevedo is] the one who takes care of [his daughter]" and on

that Wednesday when the initial transaction was scheduled, the daycare for Salinas-Acevedo's

daughter was closed -- "they had no classes. There was no school [UI] and [Salinas-Acevedo]

couldn't [participate]"). Additionally, Salinas-Acevedo informed Rullán-Santiago that he would

not participate in the first transaction the day before the transaction was scheduled.

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some evidence of improper inducement by the government. Unlike the dissent, we find that no

such evidence exists here.

While we ultimately disagree with the dissent, we note the importance of the issue before

us. On the one hand, we do not want to support a position, like the dissent's, where all a defendant

would have to show in order to be entitled to an entrapment defense is financial struggles and

repeated asks by the government. On the other hand, we also do not want to affirm a standard so

stringent that a defendant must essentially prove improper inducement beyond a reasonable doubt

in order to be afforded an entrapment jury instruction. While mindful of these competing concerns,

here, we struggle to find any evidence of improper government inducement. The mere fact that

Salinas-Acevedo had some level of financial difficulty and was asked on more than one occasion

if he wanted to participate in the sham drug deals without more is insufficient -- there must be a

"plus factor" of government overreach.4 The record provides no information regarding the

specifics of Salinas-Acevedo's financial situation beyond the fact that he was concerned about

providing for his family with the arrival of his second child. But the record does indicate that

Salinas-Acevedo was employed as a police officer. And while Salinas-Acevedo may have felt

internal pressures to participate in the drug deals for money, there is no evidence in the record of

improper attempts by the government to exploit that fact or improperly induce him to participate.

To be clear, we are not holding that repeated entreaties on any defendant, regardless of the

facts, would be permissible and insufficient to merit an entrapment defense. We merely hold that

where, as here, we have a defendant who declines to participate in illegal activity at the last minute,

but later decides to commit the offensive act without any evidence that he eventually succumbed

to governmental pressures due to changed financial means, the presentation of multiple

opportunities to commit the crime without more is insufficient to amount to improper government

4

The "plus" factors identified by the dissent appear to be an assertion that Rullán-Santiago

possessed some form of "contempt" for Salinas-Acevedo because he referred to him as a "dog"

and the dissent's insistence that there were "multiple, persistent requests by Rullán-Santiago." The

record simply does not bear these facts out. First, the inferential leap that Rullán-Santiago

possessed some sort of "contempt" or was out to get Salinas-Acevedo specifically is speculative

at best and contradicted by the record. Rullán-Santiago used foul language constantly when

referencing individuals or circumstances. For instance, in one conversation, Rullán-Santiago

referred to various individuals as "cunt," "motherfucker," "liar," and "dick." The fact that RullánSantiago, an often foul-talking individual, also referred to Salinas-Acevedo as "cabrón" or "dog"

or "cuckold" as detailed by the dissent does not demonstrate that Rullán-Santiago possessed some

overarching contempt driving him to persistently pursue Salinas-Acevedo. Second, even the

dissent concedes that the "transcripts do not reveal, however, how many times the middlemen

requested Salinas's participation." Thus, the dissent's contention that a jury could conclude that

"multiple, persistent requests by Rullán-Santiago finally broke Salinas's resistance" is unsupported

by the record -- there is no evidence beyond the three calls referenced above of requests being

made to Salinas-Acevedo. Moreover, and perhaps most importantly, even if the dissent's take on

the facts and record were true and well-supported, none of these facts demonstrate government

overreach -- the government agent (Camacho) never instructed either middleman to employ a

specific improper tactic. And merely instructing a middleman to offer Salinas-Acevedo an

opportunity to participate is insufficient.

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inducement or coercion. The dissent simply disagrees with our reading of the record. This

disagreement does not warrant rehearing.

TORRUELLA, Circuit Judge, dissenting from denial of panel rehearing. I cannot

agree with the majority's view that the present matter is merely a disagreement about how we read

the record, and thus not worthy of rehearing. I believe our disagreement is more fundamental than

that. It entails whether we recognize the legitimate role of the jury, or whether we will engage in

a usurpation of that role. Our role as presented by the record in this case is to "determine whether

the evidence is enough, 'if believed by a rational juror, to create a reasonable doubt that the

defendant committed the crime of his own accord.'" United States v. González-Pérez, 778 F.3d 3,

11 (1st Cir. 2015) (internal citations omitted). However, the majority, while paying lip service to

this role, proceeds to invert it: it reasons that because, on the record, it might be true that Salinas

was not entrapped, Salinas is therefore not allowed to argue to the jury that he was entrapped.

Thus, the majority requires Salinas to prove his defense twice: once to the court, and then once

more to the jury. In my view, this is not how things work.

The majority now recognizes that repeated requests can give rise to an entrapment defense,

but does not incorporate that understanding into its reasoning at the most crucial point. Thus, the

majority believes there is no evidence that Camacho (the government agent) instructed any of the

middlemen to use improper means, hence, the majority reasons, an entrapment defense is

inappropriate because there was no plus factor. What the majority misses is that the use of repeated

requests is itself the kind of improper inducement or plus factor that gives rise to an entrapment

defense. United States v. Gendron, 18 F.3d 961 (1st Cir. 1994) ("Some examples of improper

'inducement' may help. Courts have found a basis for sending the entrapment issue to the jury (or

finding entrapment established as a matter of law) where government officials: . . . used 'repeated

suggestions' which succeeded only when defendant had lost his job and needed money for his

family's food and rent.") (citing United States v. Kessee, 992 F.2d 1001, 1003 (9th Cir.1993)). As

I will explain below, the majority also misapplies Kessee (which found that an entrapment defense

was required, and which we cited with approval in Gendron and United States v. González-Pérez,

778 F.3d 3, 11-13 (1st Cir. 2015) (where we found that no entrapment defense was required)).

Before turning to these precedents, however, it is essential to turn to the record and the

effects it can have on a rational juror. Let me be clear, however, that I do not argue that the

disturbing aspects of the record are the improper inducement that is required for an entrapment

defense; the repeated requests are the improper inducement. However, the record underscores that

there is more than enough in this case for a rational juror to conclude that there is a reasonable

doubt that Salinas would have committed the crime of his own accord. Three aspects of the record

deserve particular attention:

1. In its January 13, 2017 decision, the majority claimed that Salinas had agreed to

participate in the drug deal after the first request, and then reneged at the last

minute. In fact, as the majority now concedes, "the record does not provide any

affirmative evidence of Salinas-Acevedo's initial agreement to participate after the

first request."

2. The majority claims that there were at most three requests. In fact, the record

supports the inference there were more than three requests.

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3. In its January 13, 2017 decision, the majority claimed that the government gave

both middlemen the instruction not to pressure Salinas. In fact, as the majority now

concedes, only Méndez-Pérez received this instruction, whereas Rullán-Santiago - who finally broke Salinas's resistance -- received no such instruction, but was told

to "get that guy" and was given a financial incentive to do so.

As the majority now concedes, there is no evidence Salinas agreed to participate in the drug

deal after the first request.5 The record reveals that Rullán-Santiago (the middleman) informed

Camacho (the government agent) that "[Salinas] sort of said it was no good, and no, no, no, no.

You know? No." As a reason for his refusal to participate in the drug deal, Salinas said "[s]orry,

it is gonna be difficult for me because of the little girl and the like." At no point in this transcript,

or at any other place in the record, does it say that Salinas had ever agreed to participate in the

drug deal -- nor does the government even claim this in its brief. Rather, the only evidence is that

Salinas repeated "no" at least six times.6

It is misleading to say, as the majority does, that there were at most three requests.7 It is

true that the record contains the transcripts of three conversations between the government agent

and the two middlemen. Those transcripts do not reveal, however, how many times the middlemen

requested Salinas's participation. Especially the second and third transcripts imply that each of the

middlemen asked Salinas multiple times to participate in the drug deal. In the second transcript,

it is Camacho (the government agent) who brings up the topic of Salinas. Méndez-Pérez (a

middleman), who was "buddies with Salinas" and who was fully aware of Salinas's financial

troubles, would go to Salinas's house. The government agent instructed this middleman that "if

[Salinas] gives you a lot of crap," then the middleman should leave Salinas alone. The government

agent did not say "any crap" or "any resistance," or something to that effect -- he said "a lot of

crap." That is, the middleman had instructions to keep making requests until he got "a lot of crap."

Thus, numerous requests likely occurred until the middleman received the requisite amount of

pushback from Salinas. In the third transcript, the government agent simply tells Rullán-Santiago

to "get that guy" -- meaning Salinas. When Rullán-Santiago asks whether he has to bring someone

to the drug deal, the agent replies "What? Of course," and then tells the middleman to "[f]ind that

5

The majority finds that the record indicates this. First, the question before us is whether a rational

juror could find for Salinas, not whether a rational juror could find against him. Suggestions in

the record that favor Salinas are therefore appropriate; suggestions that go against him are

inapposite. In any event, the suggestions the majority relies on is a reference to his daughter being

in daycare and him taking care of her made some two weeks after he declined to participate in the

first drug deal. Note also that the middleman did not believe the explanation.

6

The majority appears to emphasize that Salinas refused to participate in the transaction at the

last minute. It is unclear what the significance of this timing is for the present case -- Salinas

refused when he was approached by Rullán-Santiago, and it was thus Rullán-Santiago who chose

the timing. In any event, the record only shows that Rullán-Santiago informed Camacho on

Tuesday morning of Salinas's refusal to participate in the Wednesday transaction. The record is

silent as to when Salinas in fact refused to participate.

7

The majority claims -- without citing to the record -- that the parties agreed that there were only

three requests. The dissent has found no support for this in the record. If anything, Salinas

emphasizes the intensity with which his resistance was broken down.

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guy." That is, Rullán-Santiago will not be allowed to participate in the deal -- and thus not be

allowed to make money -- unless he succeeds in bringing someone. Rullán-Santiago, in the

meantime, had referred to Salinas as "that dog."8 Given such unambiguous instructions "to get"

Salinas, given Rullán-Santiago's financial incentive to do so, and given Rullán-Santiago's apparent

contempt for Salinas, a rational jury could conclude that multiple, persistent requests by RullánSantiago finally broke Salinas's resistance.9 Note that while Camacho had instructed MéndezPérez to leave Salinas alone if Salinas gave him "a lot of crap," Rullán-Santiago received no similar

instruction. He was never told that this deal was only for those who wanted it. He was never told

not to apply pressure. But he was told to "get that guy."

The majority here accuses the dissent of speculation. But the dissent is, in fact, fulfilling

the proper role of the court in this situation:

[i]n order to be entitled to an instruction on entrapment, the record

must show "some hard evidence" of both government inducement

and the defendant's lack of predisposition. This evidence must be

more than uncorroborated self-serving assertions. In assessing the

sufficiency of this evidence, the district court may not weigh the

evidence, make credibility determinations or resolve conflicts in the

evidence. Rather, it must determine whether the evidence is enough,

"if believed by a rational juror, to create a reasonable doubt that the

defendant committed the crime of his own accord."

González-Pérez, 778 F.3d at 11 (internal citations omitted) (emphasis added). The dissent merely

shows that Salinas has squarely met his burden of presenting enough evidence to prevail on his

entrapment defense in front of a rational jury. The majority, however, fully ignores what Salinas's

burden in fact is, and instead proceeds to do precisely what a court is prohibited from doing here:

to resolve conflicts in the evidence. Thus, the majority notes that, after Camacho told RullánSantiago to "get that guy," there was also a brief reference in the conversation to someone "from

Maricao" as a potential alternative to Salinas, and promptly concludes that Camacho merely

instructed his middleman to provide Salinas with an opportunity. Even if it were the case that this

cursory reference to an alternative target could somehow negate the clear instruction to "get that

guy," it is emphatically not the court's role to resolve this conflict in the evidence.

It is precisely the evidence that Salinas has presented that distinguishes the present case

from González-Pérez, on which the majority relies. In González-Pérez, the defendant provided

only a "bare assertion that [the confidential informant] called him several times and [the defendant]

8

In fact, Rullán-Santiago called Salinas a "cabrón." This Spanish word is far more offensive than

the English word "dog," and is more accurately translated as "cuckold."

9

The majority does not believe that Rullán-Santiago's use of foul language signifies any contempt

for Salinas, because, as the majority details, Rullán-Santiago used foul language frequently. This

only makes it more likely, however, that Rullán-Santiago's requests that Salinas participate in a

drug transaction were not polite requests -- but rather ones filled with intimating foul language -and the fact that the government agent knowingly chose exactly this middleman "to get that guy"

does not help the majority's case either.

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declined previous invitations to commit offenses . . . ." 778 F.3d at 12. Indeed, the evidence in

González-Pérez showed that the defendant was so "eager to avail himself of the opportunities to

commit the crimes that he repeatedly told [a government agent] that he was 'very grateful' and 'at

his service,' and exclaimed 'Oh wow! That's awesome, dude,' upon learning of an additional

opportunity to provide armed security." Id. at 13. In addition, González-Pérez "cite[d] no evidence

indicating that his financial situation was such that he was at a particularly vulnerable point in his

life." Id. at 12. Salinas, however, has provided hard evidence -- in the form of the transcripts of

recorded conversations -- of his several refusals to participate in the drug deal as well as of his

desperate financial situation. There is also no evidence to show that Salinas was eager to

participate in this deal -- to the contrary, he was apparently going to "jump off the balcony when

he sees [the drugs]."

The present case is not, however, distinguishable from Kessee. As the majority correctly

points out, in Kessee, the "repeated entreaties . . . only became successful when Kessee had lost

both his jobs" and "did not know where he would get the money for rent and food for his family."

Kessee, 992 F.2d at 1004. Like the defendant in Kessee, Salinas did not know how to provide for

his family now that his wife was pregnant with their second child. The majority appears to believe

that it is important that in Kessee, the defendant refused the requests to participate in a drug deal

while he was still employed, but then gave in once he had lost his jobs. That is, Kessee's resistance

ceased once his finances worsened. Salinas, however, kept resisting even though his finances were

desperate. If anything, Salinas has shown more resistance to committing a crime than Kessee had

shown, not less, and is therefore all the more deserving of an entrapment defense.

The majority also appears to suggest that the compressed time period of approximately ten

days during which the repeated requests took place works against Salinas. However, the short

intervals between the repeated requests only increase the intensity of the pressure on Salinas, and

thus only strengthen his case. Already in a desperate situation, Salinas was given little respite

from the pressure. First, Rullán-Santiago asked him to participate in the deal; Salinas refused.

Then, Méndez-Pérez came to his home; again, Salinas refused. Finally, Rullán-Santiago was out

"to get" him; Salinas finally gave in. Still, he appeared to do so reluctantly, afraid of what he was

getting himself into; in the words of Rullán-Santiago: "[Salinas] is going to jump off the balcony

when he sees [the drugs]."

This case presents the exact situation that the entrapment defense serves to protect against:

When the Government's quest for conviction leads to the

apprehension of an otherwise law-abiding citizen who, if left to his

own devices, likely would have never run afoul of the law, the courts

should intervene.

Gendron, 18 F.3d at 961 (quoting Jacobson v. United States, 503 U.S. 540, 543 (1992) and adding

emphasis). Salinas has no criminal record, nor was there even the slightest indication that he had

ever been engaged in any police corruption. Rather, he approached Rullán-Santiago to look for a

legitimate job in order to support his family. Rullán-Santiago was at that time moonlighting as the

head of security at Comp USA, and Salinas hoped to find a job as a part-time security officer at

Comp USA. He explained his dire situation to Rullán-Santiago. Rullán-Santiago informed him

‐9‐

10

Case: 13-2072

Document: 00117176055

Page: 10

Date Filed: 07/11/2017

Entry ID: 6105045

that no such jobs were available. This took place some four months before the sham drug

transaction for which Salinas is now in prison. Salinas never sought to participate in a crime, and,

if left alone by the government agent and his middlemen, likely never would have. The injustice

reaped upon Salinas by the decision of this court in foreclosing his presentation of a legitimate

claim to an entrapment defense cannot be accepted without my most fervent objection.

I dissent.

By the Court:

/s/ Margaret Carter, Clerk

cc:

Hon. Carmen Consuelo Cerezo

Frances Rios de Moran, Clerk, United States District Court for the District of Puerto Rico

Ignacio Fernandez-De-Lahongrais

Daviel Salinas-Acevedo

Myriam Yvette Fernandez-Gonzalez

Mariana E. Bauza Almonte

Eric Linden Gibson

Juan Carlos Reyes-Ramos

Robert James Heberle

‐ 10 ‐

11

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 1 of 42

United States Court of Appeals

For the First Circuit

Nos. 13-2017, 13-2047, 13-2072

UNITED STATES,

Appellee,

v.

WENDELL RIVERA-RUPERTO, a/k/a Arsenio Rivera,

MIGUEL SANTIAGO-CORDERO,

DAVIEL SALINAS-ACEVEDO,

Defendants, Appellants.

APPEALS FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF PUERTO RICO

[Hon. Carmen Consuelo Cerezo, U.S. District Judge]

Before

Torruella, Lipez, and Thompson,

Circuit Judges.

H. Manuel Hernández for appellant Wendell Rivera-Ruperto.

Ignacio Fernández de Lahongrais for appellant Daviel SalinasAcevedo.

Camille Lizarribar-Buxó on brief for appellant Miguel

Santiago-Cordero.

Robert J. Heberle, Attorney, Public Integrity Section,

Criminal Division, U.S. Department of Justice, with whom Juan

Carlos Reyes-Ramos, Assistant United States Attorney, Nelson

Pérez-Sosa, Assistant United States Attorney, Chief, Appellate

Division, and Rosa Emilia Rodríguez-Vélez, United States Attorney,

were on brief, for appellee.

12

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 2 of 42

January 13, 2017

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 3 of 42

THOMPSON, Circuit Judge.

In this appeal, Defendant-

Appellants Wendell Rivera-Ruperto, Daviel Salinas-Acevedo, and

Miguel Santiago-Cordero challenge various aspects of their trial

and sentencing.

For Rivera-Ruperto, this was his second of two

trials, which were presided over by different district judges.

Having separately addressed Rivera-Ruperto's challenges from the

first trial in a decision simultaneously released herewith, we

address in this opinion Rivera-Ruperto's challenges, as well as

those of Salinas-Acevedo and Santiago-Cordero, as to the second

trial only.

During trial, all three defendants were convicted of

various federal drug and firearms-related crimes for participating

in drug deals that were staged as a part of the FBI sting operation

"Operation Guard Shack," about which we say more in a bit.

As a

result of the convictions, each was sentenced to multiple years of

imprisonment.

In

the

present

appeal,

Rivera-Ruperto

raises

similar challenges, which we detail momentarily, to those he raised

in his appeal of his first trial and sentencing.

As for Salinas-

Acevedo, he argues the district court erred in preventing him from

presenting an entrapment defense.

Santiago-Cordero presses a

similar argument, challenging the judge's refusal to give an

entrapment jury instruction, and also appeals the district court's

denial of his post-verdict motion for acquittal.

For the reasons stated below, we affirm.

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 4 of 42

OVERVIEW

We begin with a broad overview of the facts, and later

return to the specific details of the case as they relate to the

individual defendants' arguments.

Operation Guard Shack, as we have explained in previous

decisions,1 was a large-scale investigation mounted by the FBI over

several years in order to root out police corruption throughout

Puerto Rico.

Each of the stings followed a similar pattern.

Undercover FBI informants recruited police officers to provide

armed security at drug deals staged by the FBI.

The deals took

place at FBI-monitored apartments wired with hidden cameras, and

involved undercover officers posing as sellers and buyers of sham

cocaine. In exchange for their armed security services, the police

officers were paid about $2,000 per deal.

Rivera-Ruperto, Salinas-Acevedo, and Santiago-Cordero

provided armed security at several of these Operation Guard Shack

sham drug deals between March and September of 2010.

Rivera-

Ruperto, who was not a police officer (but who was recruited

because

he

misrepresented

himself

to

the

FBI's

undercover

informant as a prison corrections officer) provided armed security

1

See, e.g., United States v. Navedo-Ramirez, 781 F.3d 563

(1st Cir. 2015); United States v. González-Pérez, 778 F.3d 3 (1st

Cir. 2015); United States v. Diaz-Castro, 752 F.3d 101 (1st Cir.

2014).

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 5 of 42

at six deals, which took place on April 9, April 14, April 27,

June 9, June 25, and September 16 of 2010.

Salinas-Acevedo and

Santiago-Cordero, who were both police officers, participated in

one deal each, on March 24, 2010, and July 8, 2010, respectively.

The government charged the three defendants with one

count each of conspiracy and attempted possession with intent to

distribute a controlled substance, as well as possession of a

firearm in relation to a drug trafficking crime.

(Various other

co-defendants were also charged, but their cases are not before

us.)

In this indictment, Rivera-Ruperto was charged for his

participation in the April 9 deal only.

For his participation in

the five later deals, Rivera-Ruperto had already been indicted

separately, tried before a different district judge, and found

guilty.

The first judge sentenced Rivera-Ruperto to 126-years and

10-months' imprisonment.

Several months after Rivera-Ruperto's first trial, he,

Salinas-Acevedo, and Santiago-Cordero were tried together in a

second proceeding, which is the subject of this appeal.

The jury

found Rivera-Ruperto guilty of all charges, and Salinas-Acevedo

and Santiago-Cordero guilty of the conspiracy and firearms counts

(it did not reach a verdict for either of them on the attempted

possession

count).

After

separate

sentencing

hearings,

the

district judge sentenced Rivera-Ruperto to 35-years imprisonment

to be served consecutively with his first sentence, resulting in

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 6 of 42

a combined prison sentence from Rivera-Ruperto's two trials that

totaled 161 years and 10 months.

Salinas-Acevedo and Santiago-

Cordero were each sentenced to 15-years and 1-month imprisonment.

The

challenges

defendants

various

aspects

timely

appealed.

of

trial

the

Rivera-Ruperto

and

sentencing,

and

Salinas-Acevedo and Santiago-Cordero of the trial only. We discuss

below each defendant in turn, beginning with Rivera-Ruperto.

DISCUSSION

I. RIVERA-RUPERTO

As we have previously noted, we issue today a companion

decision to this case affirming the district court in RiveraRuperto's first trial and sentencing.

here

are

similar

to

those

he

Rivera-Ruperto's challenges

raised

in

that

first

appeal.

Specifically, Rivera-Ruperto argues that the district court in

this second case committed reversible errors when it: (1) failed

to conduct a sua sponte inquiry to determine whether Rivera-Ruperto

had received ineffective assistance of counsel during the pleabargaining stage; (2) gave erroneous jury instructions; (3) did

not reduce his sentence on account of sentencing manipulation by

the government; and (4) sentenced him to a grossly disproportionate

sentence in violation of the Eighth Amendment.

For the reasons we

explain, each of these challenges fails in this second appeal, as

well.

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 7 of 42

A.

Lafler Claim

Rivera-Ruperto reprises a Lafler challenge that he made

(and lost) in his first appeal, in which he argues that he received

ineffective

assistance

of

counsel

during

the

plea-bargaining

phase. See Lafler v. Cooper, 132 S. Ct. 1376, 1384 (2012) (holding

that a defendant's Sixth Amendment right to competent counsel

extends to the plea-bargaining process).

Before getting to his

arguments, we give a brief recounting of what happened below.

1.

Background

We set what is quite the complicated stage by again

reminding the reader that Rivera-Ruperto eventually stood two

trials, which were presided over by different district judges.

Before the first trial began, Rivera-Ruperto was represented by

court-appointed attorney Jose Aguayo ("Aguayo"), who remained his

lawyer throughout the plea-bargaining stage.

Aguayo attempted to negotiate a plea deal for all of

Rivera-Ruperto's charges across the six sham drug deals (though

Rivera-Ruperto had been indicted separately for the charges). When

the negotiations resulted in no plea deal, the first case proceeded

toward

trial,

this

time

with

Rivera-Ruperto

represented

by

different court-appointed counsel.

Three days before that first trial was set to begin,

Rivera-Ruperto's second attorney filed a Lafler motion, alleging

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 8 of 42

that Aguayo had provided ineffective assistance of counsel at the

plea-bargaining stage.

He argued that but for Aguayo's deficient

performance, Rivera-Ruperto would have taken a 12-year plea deal

that the government had previously offered during negotiations,

and he requested that the court order the government to re-offer

that 12-year deal.

On the morning of the day the first trial was scheduled

to begin, the presiding judge held an evidentiary hearing on the

issue.

the

After considering the testimony and documentary evidence,

judge

denied

counsel claim.

Rivera-Ruperto's

ineffective

assistance

of

For reasons that we explain in detail in our

companion decision and will not rehash here, we have already

affirmed the judge's denial of Rivera-Ruperto's Lafler claim as it

pertains to his first trial.

Some

months

after

the

first

trial

and

sentencing,

Rivera-Ruperto, represented by the same attorney, stood trial a

second

time

for

the

charged

offenses

participation in the April 9 deal only.

stemming

from

his

At no time did trial

counsel request that the second judge consider the Lafler argument

Rivera-Ruperto

had

raised

and

lost

before

the

first

judge.

Therefore, no ineffective assistance of counsel claim was raised

by counsel or ruled upon by the judge in this second case.

2.

Analysis

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 9 of 42

On

appeal,

Rivera-Ruperto

acknowledges

that

counsel

during his second trial never raised the Lafler issue, but he

argues that the trial judge should nevertheless have made a sua

sponte

inquiry

and

independent

assistance of counsel claim.

ruling

on

the

ineffective

The judge's failure to do so, he

claims, was reversible error.2

Rivera-Ruperto never raised the Lafler issue before the

second presiding judge, and we assume his claim was forfeited and

not waived.

We thus review the judge's purported failure to make

a sua sponte inquiry on the ineffective assistance of counsel claim

2

The government raises a threshold argument that, because

Rivera-Ruperto had already obtained a ruling on the Lafler issue

in the first case, he was collaterally estopped from raising an

identical issue in his second trial.

Collateral estoppel, often referred to as issue preclusion,

traditionally barred civil litigants from relitigating an issue

that had already been decided in an earlier action. But it has

also become an "established rule of federal criminal law," and "is

a part of the Fifth Amendment's guarantee against double jeopardy."

United States v. Collazo-Aponte, 216 F.3d 163, 198 (1st Cir. 2000),

vacated on other grounds by 532 U.S. 1036 (2001). As such, our

case law has permitted the use of collateral estoppel in criminal

cases -- at least insofar as it is invoked by the defendant to

prevent the government from relitigating a previously-decided

issue. See id.

The parties disagree over whether collateral estoppel may be

used here, by contrast, offensively against Rivera-Ruperto.

Indeed, we know of no case in our circuit, and the government

points us to none, in which we have used collateral estoppel to

prevent a criminal defendant from raising an issue, as the

government would have us do in this case. We need not decide this

issue today, however, and will not. As we explain, even if we

assume, favorably to Rivera-Ruperto, that he is not collaterally

estopped from raising his Lafler claim, the claim still fails.

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20

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 10 of 42

for plain error.

74

(1st

Cir.

United States v. Sánchez-Berríos, 424 F.3d 65,

2005)

("[A]

waived

issue

ordinarily

cannot

be

resurrected on appeal, whereas a forfeited issue may be reviewed

for plain error".).

Reversal under plain error review is only proper if:

(1) an error occurred; (2) it was obvious; (3) it affects the

defendant's

substantial

fundamental

to

rights;

threaten

the

reputation of the proceedings.

and

fairness,

it

is

sufficiently

integrity

or

public

United States v. Delgado-Marrero,

744 F.3d 167, 184 (1st Cir. 2014).

in meeting these requirements.

(4)

Rivera-Ruperto cannot succeed

Even assuming that he clears the

first three of the plain error review hurdles, Rivera-Ruperto

cannot clear the fourth, because he cannot show that the judge's

purported

error

was

sufficiently

fundamental

to

threaten

the

fairness, integrity or public reputation of the proceedings.

In order to meet this fourth requirement, Rivera-Ruperto

would need to show that if the judge had made a sua sponte inquiry

into his ineffective assistance of counsel claim, she would indeed

have found that Rivera-Ruperto had received ineffective assistance

at

the

plea-bargaining

appropriate relief.

stage,

and

was

therefore

entitled

to

But, for reasons we explain in great detail

in our companion decision to this case, and which we will not

belabor here, we have already determined, on de novo review, that

Rivera-Ruperto was not entitled to Lafler relief, as he cannot

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21

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 11 of 42

meet the two-part ineffective assistance of counsel test laid out

in Strickland v. Washington, 466 U.S. 668, 687 (1984). See Lafler,

132 S. Ct. at 1376.

Specifically, Rivera-Ruperto is unable to

show either that Aguayo's performance was defective or that, even

if defective performance were to be assumed, it prejudiced him.

Thus, any claimed error on the second judge's part in failing to

conduct a sua sponte Lafler inquiry did not threaten the fairness

or integrity of Rivera-Ruperto's proceedings, and reversal on this

ground is not proper.

B.

Alleyne Issue

We

move

on

to

Rivera-Ruperto's

appeal

of

the

jury

instructions at his second trial, the only one of Rivera-Ruperto's

claimed errors that we have not also addressed in our companion

decision.

Rivera-Ruperto

challenges

the

jury

instructions

regarding the firearms charges only, so we focus our discussion

accordingly.

1.

First, a discussion of what happened below.

Background

Before we begin, we pause to remind the reader that at

his first trial, among other offenses, Rivera-Ruperto had been

charged with and convicted of one count of possession of a firearm

in relation to a drug trafficking crime for his participation in

each of five sham drug deals (which occurred on April 14, April

27, June 9, June 25, and September 16 of 2010).

Under 18 U.S.C.

§ 924(c)(1)(A), a defendant who is convicted of possession of a

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22

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 12 of 42

firearm in relation to a drug trafficking crime is subject to a

mandatory minimum sentence of 5-years imprisonment on the first

conviction, and then 25-years imprisonment for every subsequent

conviction, id. § 924(c)(1)(C)(i), to be served consecutively, id.

§ 924(c)(1)(D)(ii).

Accordingly, following the trial, the first

district judge sentenced Rivera-Ruperto to a total of 105 years

imprisonment for his firearms convictions (5 years for the first

§ 924(c) conviction, and 25 for each of the subsequent four

convictions).

At the second trial, Rivera-Ruperto was again tried,

among other offenses, for possession of a firearm in relation to

a drug trafficking crime, this time for his participation in the

April 9, 2010 drug deal only.

Notable for Rivera-Ruperto's

purposes, the government did not introduce at the second trial any

evidence of Rivera-Ruperto's prior § 924 convictions from his first

trial.

In addition, while the judge instructed the jury as to the

elements of the firearms offense, neither the jury instructions

nor the verdict form included prior § 924 convictions as an

"element" of the offense, or otherwise made any mention of RiveraRuperto's prior convictions.3

After deliberating, the jury found

Rivera-Ruperto guilty of all counts.

3

The verdict form, which Rivera-Ruperto did not object to,

simply stated: "We, the Jury, find defendant WENDELL RIVERA RUPERTO

___________ (GUILTY/NOT GUILTY) as charged in Count Eighteen of

the Indictment."

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23

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 13 of 42

Prior to sentencing, Rivera-Ruperto filed a sentencing

memorandum in which he argued that -- notwithstanding his five

previous § 924 convictions from the first trial -- the judge should

impose the 5-year mandatory minimum sentence for a first-time

conviction under the firearms statute, and not the 25-year minimum

for subsequent convictions.

Rivera-Ruperto argued that the judge

could not impose the "enhanced" mandatory minimum because the jury

had not made a beyond-a-reasonable-doubt finding as to his prior

§ 924 convictions.

The judge disagreed, denying the request in a written

order prior to sentencing.

After a hearing, the judge imposed the

25-year

for

minimum

sentence

a

subsequent

§

924

conviction.

Rivera-Ruperto now appeals.

2.

Analysis

Because the sentencing memorandum Rivera-Ruperto filed

before the district court preserved his Alleyne challenge, our

review of his argument on appeal is de novo.4

See Delgado-Marrero,

744 F.3d at 184.

In order to explain Rivera-Ruperto's argument, we must

first give a bit of background on the relevant case law.

At the

Count Eighteen of the Indictment charged Rivera-Ruperto with

"knowingly possess[ing] a firearm in furtherance of a drug

trafficking crime as defined in Title 18, United States Code,

Section 924(c)(2)," but made no mention of prior convictions under

18 U.S.C. § 924.

4

Jury instruction challenges generally must be preserved at

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24

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 14 of 42

time of Rivera-Ruperto's second trial, the rule was (and still is,

as we explain in a moment) that "[o]ther than the fact of a prior

conviction, any fact that increases the penalty for a crime beyond

the prescribed statutory maximum" is an element of the offense to

be found by a jury beyond a reasonable doubt.

Apprendi v. New

Jersey, 530 U.S. 466, 490 (2000) (emphasis added).

In making this

exception for prior convictions in Apprendi, the Supreme Court

deliberately left undisturbed its holding in Almendarez-Torres v.

United States, 523 U.S. 224, 226-27 (1998), which permitted the

use of prior convictions to enhance sentences without a finding by

the jury.

Between

Rivera-Ruperto's

trial

and

sentencing,

the

Supreme Court decided Alleyne v. United States, 133 S. Ct. 2151,

2155 (2013), in which it held that the Apprendi rule applied not

only to facts that increase the mandatory maximum sentence, but

also to those that increase the mandatory minimum (thus overruling

its prior holding in Harris v. United States, 536 U.S. 545, 568

(2002), which had limited Apprendi to the former).

The Supreme

Court explicitly stated, however, that its decision would leave

untouched

Almendarez-Torres's

convictions.

"narrow

exception"

for

prior

Alleyne, 133 S. Ct. at 2160 n.1.

trial, but a defendant may preserve his challenge to an

instructional Apprendi/Alleyne error by objecting at sentencing.

See United States v. Pizarro, 772 F.3d 284, 296 (1st Cir. 2014).

The government also concedes that our review here is de novo.

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 15 of 42

Despite this language in Alleyne itself, Rivera-Ruperto

argues before us that Alleyne made Almendarez-Torres inapplicable

to his case.

He seems to argue that, because Alleyne expanded the

Apprendi umbrella, bringing facts that increase mandatory minimums

under its shelter, we should, in keeping with the spirit of

Alleyne, limit Almendarez-Torres to its facts and determine that

only prior convictions that increase the prescribed maximum are

exempt from the Apprendi rule that such facts be found by a jury.

Because his prior convictions increased the prescribed minimum,

Rivera-Ruperto

argues,

they

should

be

subject

to

Alleyne's

requirement that they be found by a jury beyond a reasonable doubt.

But this is not the law.

As we have already explained,

this was not the Supreme Court's holding in Alleyne.

Moreover, we

have already rejected, in a post-Alleyne case, the argument that

prior convictions must be proven to a jury beyond a reasonable

doubt.

See United States v. Rodriguez, 759 F.3d 113, 122 (1st

Cir. 2014) (holding that the jury was not required to make a

finding

as

to

the

defendant's

Almendarez-Torres remained good law).

C.

prior

convictions

because

We therefore find no error.

Sentencing Challenges

Rivera-Ruperto's remaining two challenges concern his

sentence.

He argues, as he did in his appeal from the first trial,

that the government engaged in improper sentencing manipulation,

and that his sentence across the two trials, for a combined 161-

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 16 of 42

years and 10-months' imprisonment, violates the Eighth Amendment's

prohibition on cruel and unusual punishment.

In raising these

arguments in the present appeal, Rivera-Ruperto incorporates by

reference the sections of his brief from his appeal in the first

trial.

As we have already discussed these arguments in detail in

our companion decision, we keep our recounting of what happened

concise.

1.

Background

At the first trial, the jury found Rivera-Ruperto guilty

of five counts each (one for each of the five charged drug deals)

of conspiracy and attempted possession with intent to distribute

5 kilograms or more of a controlled substance and of possession of

a firearm in relation to a drug trafficking crime.

It also found

Rivera-Ruperto guilty of one count of possession of a firearm with

an obliterated serial number.

At sentencing, Rivera-Ruperto argued that the FBI's use

of "large" quantities of sham cocaine at each of the drug deals,

its request that he bring a firearm to each of the deals, its

decision to allow him to participate in multiple deals, and its

decision to charge him separately for each of the deals all

constituted improper sentencing manipulation because, he claimed,

the government made those choices for the sole purpose of exposing

him to an enhanced sentence.

The first district judge disagreed,

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27

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 17 of 42

and sentenced Rivera-Ruperto to 126 years and 10 months for the

crimes.

At his second trial, Rivera-Ruperto was again found

guilty, this time of one count each of three crimes (for the

remaining

April

9

drug

deal

only):

conspiracy

and

attempted

possession with intent to distribute 5 kilograms or more of a

controlled substance, and possession of a firearm in relation to

a drug trafficking crime.

After

Ruperto's

a

sentencing

counsel

did

not

hearing,

raise

a

during

which

sentencing

Rivera-

manipulation

objection, the second district judge sentenced Rivera-Ruperto to

the statutory minimum of 10-years imprisonment for the conspiracy

and

attempt

counts

and

the

statutory

imprisonment for the firearms count.

minimum

of

25-years

Rivera-Ruperto was thus

sentenced to a total of 35-years imprisonment, to be served

consecutively to his 126-year and 10-month sentence from the first

trial.

2.

Sentencing Manipulation

Because

Rivera-Ruperto

did

not

raise

a

sentencing

manipulation challenge before the second district judge, we review

for plain error.5

See Sánchez-Berríos, 424 F.3d 65 at 78.

5

Rivera-Ruperto did raise his sentencing manipulation

argument during his first sentencing hearing before the first

district judge, and it would therefore be reasonable to treat the

sentencing manipulation argument as altogether waived as to his

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 18 of 42

Rivera-Ruperto argues that the government engaged in

sentencing manipulation by using unnecessarily high quantities of

sham drugs during the deals, requiring Rivera-Ruperto to bring a

firearm with him to each of the deals, and then allowing him to

participate in a "seemingly endless" number of those deals.

We

need not tarry in our consideration of Rivera-Ruperto's sentencing

manipulation argument here.

in

detail

why

manipulation

In our companion decision, we explain

Rivera-Ruperto's

argument

fails

fact-determinative

under

a

clear-error

sentencing

standard

of

review. In renewing his challenge as to this second trial, RiveraRuperto has added no new argument, choosing merely to incorporate

by reference the sections of his brief from his first appeal.

Because Rivera-Ruperto has adopted his briefing from the first

case wholesale, the only difference in our review here is that the

more rigorous plain-error standard applies.

Given that Rivera-

Ruperto's sentencing manipulation challenge failed under the less

exacting standard in the first case, it also fails here.

3.

Eighth Amendment

The same is true of Rivera-Ruperto's final challenge:

his argument that his total sentence from the two trials of 161years and 10-months' imprisonment violates the Eighth Amendment's

second sentence. The government, however, does not argue waiver

in its brief. Thus, favorably to Rivera-Ruperto, we review for

plain error.

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 19 of 42

prohibition on cruel and unusual punishment.

Here, Rivera-Ruperto

again adopts by reference the Eighth Amendment section of his brief

in the first appeal, which fails for the reasons we have already

explained in our decision in that case.

For the reasons stated in

our companion opinion, Rivera-Ruperto's sentence is affirmed.

II. SALINAS-ACEVEDO

We turn now to Salinas-Acevedo's appeal.

As we noted

above, Salinas-Acevedo was indicted on charges of conspiracy to

distribute and attempted possession with the intent to distribute

more than 5 kilograms of cocaine, as well as of possession of a

firearm in furtherance of a drug crime, for his participation in

one Operation Guard Shack deal on March 24, 2010.

The jury found

Salinas-Acevedo guilty of the conspiracy and firearm counts, but

did not reach a verdict as to the attempted possession count.

Salinas-Acevedo was sentenced to a total of 15-years and 1-month

imprisonment.

Salinas-Acevedo raises just one argument on appeal.

He

argues that the district court erred in preventing him from

presenting an entrapment defense at trial.

We begin with a

discussion of what happened below.

A.

Background

1.

On

Lead-Up to the March 24 Deal

March

24,

2010,

fellow

police

officers

Salinas-

Acevedo, Alwin Camacho ("Camacho"), and Israel Rullán-Santiago

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 20 of 42

("Rullán-Santiago")6 provided armed security at an Operation Guard

Shack drug deal.

What Salinas-Acevedo did not know at the time

was that Camacho was working undercover as an FBI informant to

recruit corrupt police officers for Operation Guard Shack.

Camacho had targeted Rullán-Santiago after he heard

Rullán-Santiago bragging around the station that he knew drug

traffickers and was "basically a delinquent using up the uniform."

It was Rullán-Santiago who, in turn, recruited his friend SalinasAcevedo. Both Rullán-Santiago and Camacho were aware that SalinasAcevedo had a daughter and was expecting another child, and that

he was in a difficult financial situation.

Originally, Salinas-Acevedo was supposed to participate

in a drug transaction that had been planned for March 10, 2010.

But,

according

to

a

recorded

telephone

conversation

between

Rullán-Santiago and Camacho on the night before that deal, SalinasAcevedo, seemingly referring to his child, backed out at the last

minute, telling Rullán-Santiago, "Sorry, it's gonna be difficult

for me because of the little girl and the like."

Hearing that

Salinas-Acevedo would not make it to the deal, Camacho postponed

the scheduled transaction.

Shortly thereafter, Camacho was also recorded talking to

Carlos Méndez-Pérez ("Méndez-Pérez"), yet another police officer

6

Rullán-Santiago was one of the co-defendants in this case

below, but is not a party to this appeal.

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 21 of 42

who would himself participate in Operation Guard Shack and be

charged separately in a different case.

During the conversation,

Camacho

Camacho

brought

up

Salinas-Acevedo.

asked,

"[S]ince

you're buddies with Salinas, what do you think about Salinas?"

He

went on to say, "Because, um, Rullán approached him and later he

gave me excuses that his daughter . . . ."

Camacho told Méndez-

Pérez that Rullán-Santiago had told him that Salinas-Acevedo was

"willing to do anything and he's broke."

Camacho also told Méndez-Pérez that he had directed

Rullán-Santiago not to "bring up that topic with [Salinas-Acevedo]

anymore."

But later in the conversation, Camacho told Méndez-

Perez to talk to Salinas-Acevedo and have him "come by" to see

him.

In response, Méndez-Pérez told Camacho that he would stop by

Salinas-Acevedo's house.

Camacho instructed Méndez-Pérez to find

out what days Salinas-Acevedo "ha[d] available," but also directed

Méndez-Pérez, "[I]f he gives you a lot of crap[;] . . . [t]his

isn't compulsory, this is for those who want to and know what it

is."

On

conversation

March

with

19,

2010,

in

Rullán-Santiago,

another

Camacho

recorded

directed

phone

Rullán-

Santiago to "get that guy that you tried to find last time," by

which he meant Salinas-Acevedo.

Rullán-Santiago responded, "[L]et

me see if, . . . if that dog is around here."

- 21 -

Camacho replied,

32

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 22 of 42

"Well, but let me know for sure, don't do the same shitty thing to

me like you did last week."

Three days later, Camacho, who by then presumably knew

Salinas-Acevedo had agreed to the job, called Rullán-Santiago to

"double check[]" that Rullán-Santiago and Salinas-Acevedo were

both on board for the upcoming March 24 drug deal.

In a not-

entirely-clear exchange, Camacho asked Rullán-Santiago, "You told

Salinas what it was, right, the devices?" Rullán-Santiago at first

told Camacho "Yes," but then laughed and told Camacho that SalinasAcevedo would "jump off the balcony when he sees [the drugs]."

The story ends, as we know, with the deal going down as

planned, with Rullán-Santiago and Salinas-Acevedo being arrested

and brought up on charges, and with Salinas-Acevedo standing

trial.7

2.

Lead-Up to Trial

Before trial, the government moved in limine to preclude

Salinas-Acevedo from raising an entrapment defense in his opening

statement.

The district court initially denied the motion, but

when the government filed a motion for reconsideration of the

order, the trial court ordered Salinas-Acevedo to proffer his

evidence supporting an entrapment defense.

7

Rullán-Santiago took a plea

sentenced to 19-years imprisonment.

- 22 -

deal,

and

was

eventually

33

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 23 of 42

Salinas-Acevedo proffered the following.

First, he

asserted that, at all relevant times, Camacho had been aware of

Salinas-Acevedo's difficult financial situation because SalinasAcevedo had previously asked Camacho about part-time opportunities

at CompUSA, where Camacho worked as a part-time security guard,

and Camacho had told Salinas-Acevedo that he would let him know if

any opportunities opened up.

Second, Salinas-Acevedo submitted a

transcript

conversations

of

the

recorded

between

Camacho

and

Rullán-Santiago and Méndez-Pérez, which Salinas-Acevedo argued

showed that Camacho had targeted and incited Salinas-Acevedo into

participating in the sham drug deals.

Finally,

Salinas-Acevedo

alleged

that

he

had

been

wrongly induced into committing the crime because Rullán-Santiago

had told him that the March 24 transaction was a "legitimate

business transaction" involving the sale of diamonds, and that it

was only after he had arrived at the location that it was revealed

to him that it was a drug deal.

However, at the court's subsequent

prompting, Salinas-Acevedo conceded that he did not have any

evidence

that

the

government

(through

Camacho)

had

directed

Rullán-Santiago to tell Salinas-Acevedo that it was a legitimate

transaction, or that Camacho was otherwise responsible for the

alleged misinformation.

By sealed ex parte order, the court held that this was

an "insufficient basis to allow defendant Salinas to mention to

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 24 of 42

the jury in opening statements a defense of entrapment," and

vacated its previous order denying the government's motion in

limine. Accordingly, Salinas-Acevedo was not permitted to mention

entrapment in his opening statement.

At trial, over the objections of Rivera-Ruperto and

Santiago-Cordero (our third co-defendant in this appeal, who we

will get to know better shortly), the district court declined to

give the jury an instruction on the entrapment defense.

Salinas-

Acevedo did not join in that objection to the jury instructions.

Salinas-Acevedo now appeals, arguing that the district court erred

in preventing him from raising an entrapment defense.

B.

Analysis

requested

The

government

argues

that

an

entrapment

instruction,

Salinas-Acevedo

neither

nor

his

joined

in

co-

defendants' jury instruction objection during trial, and that his

claim is therefore unpreserved and subject to plain error review.

See United States v. Guevara, 706 F.3d 38, 46 (1st Cir. 2013).

Salinas-Acevedo argues that our review is de novo, presumably on

a theory that his objection to the government's motion in limine

was sufficient to preserve his objection to being denied a jury

instruction on entrapment as well.

But even assuming, favorably

to Salinas-Acevedo, that the claim was properly preserved, the

argument still fails under de novo review.

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 25 of 42

The judicially-created doctrine of entrapment exists "to

prevent 'abuse[]' of the 'processes of detection and enforcement

. . . by government officials' who might instigate an illegal 'act

on the part of persons otherwise innocent in order to lure them to

its commissions and to punish them.'"

United States v. Díaz-

Maldonado, 727 F.3d 130, 137 (1st Cir. 2013) (quoting Sorrells v.

United States, 287 U.S. 435, 448 (1932)) (alteration and omission

in original). A defendant seeking to present an entrapment defense

at trial must satisfy an "entry-level burden of production."

Sánchez-Berríos, 424 F.3d at 76.

He must produce "evidence which

fairly supports the claims" that: (1) the government agents not

only induced the crime but did so improperly, and (2) that he was

not already predisposed to commit the crime.

Id. at 76-77.

In determining whether a defendant has met this two-part

burden, a court "is to examine the evidence on the record and to

draw

those

inferences

as

can

reasonably

be

drawn

therefrom,

determining whether the proof, taken in the light most favorable

to the defense can plausibly support the theory of the defense."

United States v. Gamache, 156 F.3d 1, 9 (1st Cir. 1998).

If the

defendant succeeds and the defense is introduced at trial, it

becomes the government's obligation to prove beyond a reasonable

doubt that no entrapment occurred.

We

begin

by

examining

whether

Salinas-Acevedo

has

satisfied the improper inducement prong of his two-part burden.

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 26 of 42

Because Salinas-Acevedo did not deal directly with Camacho -- the

"government agent" in this case, see United States v. Luisi, 482

F.3d 43, 53 (1st Cir. 2007) (explaining that an individual hired

as a government informant constitutes a government agent for

entrapment

purposes)

--

but

middleman

(Rullán-Santiago),

was

brought

into

Salinas-Acevedo

derivative theory of entrapment.

the

deal

by

a

must

rely

on

a

Under this theory, the conduct

of a middleman is only attributable to the government where:

(1) the government agent specifically targeted the

defendant in order to induce him to commit illegal

conduct; (2) the agent acted through the middleman after

other government attempts at inducing the defendant had

failed; (3) the government agent requested, encouraged,

or instructed the middleman to employ a specified

inducement, which could be found improper, against the

targeted defendant; (4) the agent's actions led the

middleman to do what the government sought, even if the

government did not use improper means to influence the

middleman; and (5) as a result of the middleman's

inducement, the targeted defendant in fact engaged in

the illegal conduct.

Luisi, 482 F.3d at 55.

Salinas-Acevedo

requirements.

satisfies

the

first

two

of

these

The recorded conversations proffered by Salinas-

Acevedo show Camacho more than once asking Rullán-Santiago and

Méndez-Pérez about Salinas-Acevedo, and encouraging them to get

Salinas-Acevedo involved in the drug deals.

Viewing the evidence

in the light most favorable to Salinas-Acevedo, a jury could

conclude that Camacho targeted Salinas-Acevedo and used at least

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 27 of 42

Rullán-Santiago,

if

not

both

middlemen,8

to

induce

him

to

participate in the March 24 transaction.

In

order

to

meet

the

third

requirement,

however,

Salinas-Acevedo must show that the government (via its agent

Camacho)

encouraged

Rullán-Santiago

"improper" inducement.9

Id.

to

employ

a

specific

The key issue here is whether a

specified improper inducement by Rullán-Santiago (or Méndez-Pérez)

can be attributed to the government itself.

The government would

be responsible for any improper inducement by either middleman if

8

It appears Méndez-Pérez may not have attempted to recruit

Salinas-Acevedo. The video recording from the March 24 drug deal

shows Camacho asking Salinas-Acevedo if he knows anyone

"trustworthy" that he would recommend for future deals, to which

Salinas-Acevedo suggests his "buddy" Méndez-Pérez, and then

appears surprised to hear that Méndez-Pérez was "already part of

the clan." The government argues that if Méndez-Pérez had actually

induced Salinas-Acevedo into participating in the March 24 drug

deal, Salinas-Acevedo would not have been surprised to hear he was

already in on the conspiracy. Salinas-Acevedo does not challenge

this argument.

9

Salinas-Acevedo appears to raise an alternative argument in

his reply brief that he was not required to meet this third factor

at all, and that the factors laid out in Luisi, 482 F.3d at 55,

are merely factors for the district court to weigh in assessing a

defendant's derivative entrapment theory. We need not address an

argument raised for the first time in a party's reply brief. See

N. Am. Specialty Ins. Co. v. Lapalme, 258 F.3d 35, 45 (1st Cir.

2001) ("[A]bsent exceptional circumstances, an appellant cannot

raise an argument for the first time in a reply brief."). Nor

would it make any difference here because Salinas-Acevedo is

incorrect. All five Luisi factors must be met in order to warrant

an entrapment instruction based on the conduct of a middleman.

See Luisi, 482 F.3d at 55; see also United States v. NavedoRamirez, 781 F.3d 563, 570 n.1 (1st Cir. 2015) (describing the

Luisi factors as "conditions" that must be "satisfied").

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 28 of 42

its agent (Camacho) had "told" or "instructed" the middleman

(Rullán-Santiago or Méndez-Pérez) to apply the inducement later

deemed improper.

See United States v. Rogers, 102 F.3d 641, 645

(1st Cir. 1996) ("Under the case law the government would be

responsible if [its agent] told [the middleman] to apply the

pressure or inducement later deemed improper, and perhaps if [the

government's

agent]

knowingly

tolerated

it,

but

not

if

[the

government's agent] were ignorant of it."); Luisi, 482 F.3d at 55.

For

example,

in

Rogers,

a

government

agent

was

introduced to a third-party middleman who engaged the defendant in

a conspiracy to purchase drugs with the intent to sell.

The

defendant argued that the middleman should be treated as an

"unwitting government agent."

disagreed,

finding

that

Rogers, 102 F.3d at 645.

there

was

insufficient

We

evidence

associating the government's agent with any improper inducement by

the middleman.

Id.

We specifically noted that even if the

middleman did act improperly, nothing in the record demonstrated

that the government agent "urged, suggested, or was even aware of"

the improper conduct referenced by the defendant.

Similarly,

here,

the

record

negates

Id.

a

finding

of

improper inducement by the government itself (via its agent,

Camacho).

On multiple occasions, Camacho told his intermediaries

not to pressure Salinas-Acevedo to participate in the drug deals.

While Camacho repeatedly asked the middlemen to check on Salinas-

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 29 of 42

Acevedo's availability and willingness to participate, there is no

evidence that he urged them to apply improper pressure on SalinasAcevedo

to

specifically

join

the

enterprise.

To

the

contrary,

Camacho

directed

Méndez-Pérez

that

"if

[Salinas-Acevedo]

gives you a lot of crap[;] . . . [t]his isn't compulsory, this is

for those who want to and know what it is."

And although Camacho did direct Rullán-Santiago to get

Salinas-Acevedo ("that guy that you tried to find last time") to

participate and Rullán-Santiago responded that he would see "if

that dog is around here," Camacho never insisted that RullánSantiago

do

whatever

it

takes

to

get

Salinas-Acevedo

to

participate. Instead, Camacho's reply -- "don't do the same shitty

thing to me like you did last week" -- appears to be a warning

about adequate notice, given that Rullán-Santiago had backed out

of the first transaction at the last minute and Camacho wanted

Rullán-Santiago to let him know "for sure" -- one way or another

-- whether Salinas-Acevedo would participate.

Salinas-Acevedo

must show not only that Camacho, through his middlemen, gave him

the opportunity to commit the crime, but also a "plus" factor -an inducement amounting to some kind of "government overreach."

Guevara, 706 F.3d at 46.

Even if we were to assume that actions

of the middlemen here were improper, Salinas-Acevedo has failed to

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 30 of 42

produce

sufficient

evidence

of

government

overreach

or

arm-

twisting in this case.10

Salinas-Acevedo has thus failed to meet the improper

inducement prong of his two-prong burden, and we need not proceed

to the second question of whether he was already predisposed to

commit the crime.

The district court did not err in denying

Salinas-Acevedo an opportunity to present an entrapment defense.

III. SANTIAGO-CORDERO

The

last

of

the

three

defendants

in

this

appeal,

Santiago-Cordero, participated in an Operation Guard Shack drug

deal on July 8, 2010, and was tried for one count each of conspiracy

10

We do not consider Salinas-Acevedo's originally-proffered

claim that Rullán-Santiago duped him into participating in the

March 24 deal by misrepresenting it as a legitimate business

transaction over the sale of diamonds. Salinas-Acevedo conceded

below that he had no proof that it was Camacho who directed or in

any way encouraged Rullán-Santiago to tell him this lie.

See

United States v. Gates, 709 F.3d 58, 63 (1st Cir. 2013) ("[A] party

cannot concede an issue in the district court and later, on appeal,

attempt to repudiate that concession and resurrect the issue. To

hold otherwise would be to allow a litigant to lead a trial court

down a primrose path and later, on appeal, profit from the invited

error."). Because Salinas-Acevedo has no evidence connecting the

purported misrepresentation to a government agent, it does not

factor into our derivative entrapment analysis.

Although Salinas-Acevedo was not permitted to argue that he

was lied to as part of an entrapment defense, we note that he did

have an opportunity to do so at trial as part of his argument that

he lacked the mens rea to commit the crime. The jury was thus

presented evidence of the alleged misrepresentation -- including

the phone conversation in which Rullán-Santiago told Camacho that

Salinas-Acevedo would "jump off the balcony" upon seeing the drugs

-- and had the opportunity to consider it in coming to its verdict.

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 31 of 42

to

distribute

and

attempted

possession

with

the

intent

to

distribute more than 5 kilograms of cocaine, as well as possession

of a firearm in furtherance of a drug crime.

The jury found

Santiago-Cordero guilty of the conspiracy and firearm counts, but

did not reach a verdict as to the attempted possession count.

For

his crimes, Santiago-Cordero was sentenced to 15-years and 1-month

imprisonment.

Santiago-Cordero raises two issues on appeal.

like

Salinas-Acevedo,

he

appeals

the

district

court's

denying him a jury instruction on an entrapment defense.

First,

ruling

Second,

he appeals the district court's denial of his motion for acquittal.

We start again with what happened below.

A.

Background

This has, by now, become a familiar scene with a familiar

cast of characters, so we will do our best to keep our narration

short.

Camacho and Rullán-Santiago reprise the same roles here

that they played in Salinas-Acevedo's story, as confidential FBI

informant

and

unsuspecting

middleman

turned

co-defendant,

respectively.

As he had done with Salinas-Acevedo, Rullán-Santiago

(with

Camacho's

blessing)

recruited

Operation Guard Shack drug deal.

Santiago-Cordero

for

an

Camacho was apparently aware in

the lead-up to the deal that Santiago-Cordero was money-strapped,

because during the phone calls in which they discussed bringing

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 32 of 42

Santiago-Cordero

on

board,

Rullán-Santiago

told

Camacho

that

Santiago-Cordero was in need of money.

On July 8, 2010, as planned, Santiago-Cordero arrived

with firearm in tow at the apartment where the sham drug deal would

take place.

Unaware that he was being surveilled by the FBI,

Santiago-Cordero provided security services at the deal, where

undercover officers posing as drug dealers exchanged sham cocaine

bricks for large amounts of cash.

After the deal was completed,

Santiago-Cordero was paid $2,000.

This was all caught on film.

Santiago-Cordero

was

arrested

shortly

thereafter,

charged, and stood trial along with Rivera-Ruperto and SalinasAcevedo.

During trial, the prosecution introduced testimony from

Camacho, as well as the video footage of the deal.

Toward

conference.

trial's

end,

the

court

held

a

jury

charge

There, counsel for Santiago-Cordero requested that

the jury be instructed on an entrapment defense, which the judge

denied.

After deliberations, the jury found Santiago-Cordero

guilty of the conspiracy and firearm counts, but did not reach a

verdict as to the attempted possession count.

About

a

week

after

trial,

Santiago-Cordero

filed

a

motion for acquittal, in which he argued that his conviction should

be vacated because the evidence had been insufficient to support

the jury's verdict on the conspiracy count.

The judge denied the

motion,

sentenced

and,

after

a

sentencing

- 32 -

hearing,

Santiago-

43

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 33 of 42

Cordero to 15-years and 1-month imprisonment.

now

appeals

both

the

sufficiency

of

the

Santiago-Cordero

evidence

and

jury

instruction issues.

B.

Analysis

1.

Sufficiency of the Evidence

Santiago-Cordero argues, as he did in his motion for

acquittal below, that both his convictions should be overturned

because: (1) the government presented inadequate evidence at trial

to

support

a

guilty

verdict

on

the

conspiracy

charge,

and

(2) without the conspiracy conviction, there was no "drug crime"

on which his conviction for possession of a firearm in furtherance

of a drug crime could be based. Because Santiago-Cordero preserved

his sufficiency of the evidence argument, we apply de novo review.

See United States v. Adorno-Molina, 774 F.3d 116, 121 (1st Cir.

2014).

In order to return a conspiracy conviction under 21

U.S.C. § 846, the government must show that: "(1) a conspiracy

existed; (2) the defendant had knowledge of the conspiracy; and

(3) the defendant knowingly and voluntarily participated in the

conspiracy."

2013).

element,

United States v. Maryea, 704 F.3d 55, 73 (1st Cir.

Here, Santiago-Cordero takes issue with the "knowledge"

arguing

that

at

trial

the

government

presented

insufficient evidence that he knew the transaction involved the

distribution of drugs.

He contends that the video footage shows

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 34 of 42

that drugs were never explicitly discussed during the transaction,

and that he never looked inside the wrapped packages to confirm

that they, in fact, contained drugs.

He also argues that Camacho

testified at trial that he did not know what Santiago-Cordero had

been

told

about

the

transaction

by

Rullán-Santiago,

and

government never put Rullán-Santiago himself on the stand.

the

Thus,

he claims, the government's evidence was insufficient to prove

beyond a reasonable doubt that he had knowledge of the nature of

the conspiracy.

But a jury verdict will not be overturned so long as we

find that a rational factfinder could have found that the evidence

presented at trial, "together with all reasonable inferences,

viewed in the light most favorable to the government," established

each element of the offense beyond a reasonable doubt.

States v. Poulin, 631 F.3d 17, 22 (1st Cir. 2011).

United

Given this

difficult standard, defendants raising this claim are "rarely

successful," United States v. Moran, 984 F.2d 1299, 1300 (1st Cir.

1993), and Santiago-Cordero is no exception.

To sustain a conspiracy conviction under § 846, the

government "need only prove that the defendant had knowledge that

he was dealing with a controlled substance, not that he had

knowledge of the specific controlled substance."

Woods, 210 F.3d 70, 77 (1st Cir. 2000).

United States v.

Here, the government

introduced at trial video footage of Santiago-Cordero, who the

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45

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 35 of 42

jury knew was a trained police officer, showing up for the July 8

deal armed with his firearm and ready to provide security.

Santiago-Cordero

frisked

the

undercover

buyer

upon

arrival at the deal site, and then watched as a substance packaged

in bricks and marked with logos (in the same manner as cocaine is

usually packaged) was exchanged for cash.

See United States v.

Azubike, 564 F.3d 59, 65 (1st Cir. 2009) (explaining that where

the jury was shown evidence that "the modus operandi of the crime

was the same as that of drug transactions sadly common in this

geographic area," this "support[ed] the jury's conclusion that

defendant knew he was transporting drugs").

Santiago-Cordero was

then paid $2,000 for what amounted to less than an hour of work.

The government also presented the jury with a recorded

phone call in which Rullán-Santiago told Camacho that he had

informed Santiago-Cordero that they would be working a drug deal,

as well as footage from the July 8 deal in which Camacho asks

Santiago-Cordero,

"Rullán

already

explained

Santiago-Cordero answers in the affirmative.

it

to

you?,"

and

On this evidence, a

jury had a more than adequate basis to come to its conclusion that

Santiago-Cordero had knowledge of the nature of the conspiracy.

We thus affirm.

2.

Entrapment Defense

We turn to Santiago-Cordero's appeal of the judge's

denial of an entrapment defense instruction.

- 35 -

Because he raised

46

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 36 of 42

the objection below, our review is de novo.

See Azubike, 564 F.3d

at 64.

Having already mapped out the doctrine of derivative

entrapment in our previous discussion of Salinas-Acevedo's appeal,

we keep our discussion of Santiago-Cordero's entrapment argument

short.

Recall that a defendant is only entitled to an entrapment

defense if he can establish the government agents improperly

induced a crime that he was not already predisposed to commit.

Sánchez-Berríos, 424 F.3d at 76-77.

Here, the only evidence that

Santiago-Cordero has produced of improper inducement is that the

government knew he was "broke and needed money," and that the

government

knew

that

its

middleman,

Rullán-Santiago,

was

a

"delinquent" and used him anyway to recruit Salinas-Acevedo.

Awareness on the part of the government of a targeted

defendant's difficult financial situation does not, without more,

constitute improper inducement.

See, e.g., United States v.

Baltas, 236 F.3d 27, 37 (1st Cir. 2001). As for Santiago-Cordero's

suggestion that using Rullán-Santiago as a middleman despite his

shady reputation somehow constituted improper inducement, this

misses the mark, too.

As we explained above, the focus in an

improper inducement inquiry is on the government's tactics for

recruiting

the

defendant.

Rullán-Santiago

may

have

been

of

disreputable character, but Santiago-Cordero has not identified

any

specific

conduct

on

Rullán-Santiago's

- 36 -

part,

whether

at

47

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 37 of 42

Camacho's

behest

inducement.

or

otherwise,

that

constitutes

improper

Thus, Santiago-Cordero did not meet his burden of

production on an entrapment defense, and was not entitled to an

instruction at trial.

CONCLUSION

For the reasons we have stated above, we affirm.

-Dissenting Opinion Follows-

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48

Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 38 of 42

TORRUELLA, Circuit Judge (Dissenting in Part).

The

majority holds that, as a matter of law, repeated suggestions

cannot give rise to a defense of entrapment.

dissent.

I respectfully

The purpose of sting operations is to bring willing

perpetrators to justice, not to induce law-abiding citizens to

err.

Repeated suggestions are precisely one way to induce law-

abiding citizens to err -- especially where, as here, those lawabiding citizens are in dire financial straits.

Because the majority has already laid out the facts of

this case, I summarize only the key facts here.

Salinas-Acevedo

was in debt, had a little daughter, and another child on the way

-- his financial situation was difficult, to say the very least.

Both the government agent and the middlemen knew this.

Still,

Salinas-Acevedo showed great reluctance to become involved in any

illegal drug transaction.

The middleman had to approach Salinas-

Acevedo multiple times in order to induce him to participate in

the drug transaction. Although Salinas-Acevedo initially agreed,

he later pulled out of the transaction on account of his little

girl.

It was only after being approached by the middleman again

that Salinas-Acevedo finally gave in and reluctantly participated

in the drug transaction.

The middleman's actions were all on the

direct instructions of the government agent.

Indeed, the final

instructions of the government agent to the middleman were "Hey,

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 39 of 42

get that guy," "find, find that guy," and, once more, "[f]ind that

guy" -- all referring to Salinas-Acevedo.

I agree with the majority that we are here faced with

derivative entrapment, and that the test for that has five prongs:

(1) a government agent specifically targeted

the defendant in order to induce him to commit

illegal conduct; (2) the agent acted through

the middleman after other government attempts

at inducing the defendant had failed; (3) the

government agent requested, encouraged, or

instructed the middleman to employ a specified

inducement, which could be found improper,

against the targeted defendant; (4) the

agent’s actions led the middleman to do what

the government sought, even if the government

did not use improper means to influence the

middleman; and (5) as a result of the

middleman’s

inducement,

the

targeted

defendant in fact engaged in the illegal

conduct.

United States v. Luisi, 482 F.3d 43, 55 (1st Cir. 2007).

I also agree with the majority that the first two prongs

of this test are satisfied -- but unlike the majority, I believe

that the third prong is satisfied as well.11

The

majority

takes

great

comfort

in

the

fact

that

"[u]nder the case law the government would be responsible if [its

agent] told [the middleman] to apply the pressure or inducement

11

Because the majority does not believe that the third prong

is satisfied here, it does not reach the fourth and fifth ones.

For the same reason, the majority also does not reach the improper

inducement prong of the entrapment analysis. On the facts of this

case, I have no difficulty finding that all these prongs have been

met.

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 40 of 42

later deemed improper, and perhaps if [the government agent]

knowingly tolerated it, but not if [the government agent] were

ignorant of it."

Cir.

1996).

United States v. Rogers, 102 F.3d 641, 645 (1st

The

majority

then

reasons

that

there

are

no

indications that the government agent engaged in any improper

inducement; the majority emphasizes that even if the middleman

somehow did engage in improper inducement, then there is no

indication that the government agent had told the middleman to do

so.

However, "examples of improper 'inducement'" include the

use of "'repeated suggestions' which succeeded only when the

defendant had lost his job and needed money for his family's food

and rent."

United States v. Gendron, 18 F.3d 955, 961 (1st Cir.

1994)(Breyer, C.J.)(quoting United States v. Kessee, 992 F.2d

1001, 1003 (9th Cir. 1993)).

In the present case, the government

agent told the middleman to engage in exactly this kind of improper

inducement, for the government agent told the middleman to approach

Salinas-Acevedo repeatedly about the drug transaction, knowing

full well that Salinas-Acevedo had serious difficulties providing

for his family, and that he had declined to participate numerous

times.12

12

Another example of improper inducement is "dogged

insistence until [defendant] capitulated". Gendron, 18 F.3d at

961 (quoting United States v. Rodriquez, 858 F.2d 809, 815 (1st

Cir. 1988)(alteration in original); see also United States v.

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 41 of 42

Other circuits have also found that repeated suggestions

constitute

improper

inducement

for

entrapment

purposes.

See

United States v. Mayfield, 771 F.3d 417, 435 (7th Cir. 2014)(en

banc)(holding that improper inducement "may be repeated attempts

at persuasion"); United States v. Kessee, 992 F.2d 1001, 1004 (9th

Cir. 1993)("[The government agent] induced [the defendant] to sell

narcotics by repeated entreaties, which only became successful

when [the defendant] had lost both his jobs and desperately needed

the money . . . A jury could have had a reasonable doubt as to

inducement or lack of predisposition"); United States v. Burkley,

591 F.2d 903, 915 (D.C. Cir. 1978) ("[T]he trial judge correctly

issued

an

entrapment

instruction

because

(1)

[the

government

agent]'s repeated requests constituted sufficient evidence of

inducement").

It is not surprising that our sister circuits have come

out this way, because the Supreme Court has found entrapment (even

as a matter of law) where repeated suggestions were involved.

Retracing the Supreme Court's key entrapment

cases may help illuminate the problem . . .

Montoya, No. 15-2089, 2016 WL 7336577, at *2 (1st Cir. Dec. 19,

2016) ("[Improper inducement] might include, for example, . . .

relentless insistence . . . to participate in a criminal scheme).

In the present case, I have no difficulty finding that the

government agent told the middleman to engage in "dogged

insistence" or "relentless insistence." This dissent focuses on

"repeated suggestions" in light of defendant's difficult financial

situation, because the facts of this case shout out "repeated

suggestions" even more loudly than they do "dogged insistence" and

"persistent insistence."

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Case 3:10-cr-00342-CCC-SCC Document 625 Filed 01/17/17 Page 42 of 42

In Sorrells the Court found that an entrapment

instruction

was

warranted

.

.

.

the

informant's persistent appeal to military

camaraderie

qualified

as

a

potentially

entrapping inducement.

[Sorrells v. United

States, 287 U.S. 435, 441 (1932).] In Sherman

the Court found entrapment as a matter of law

. . . the inducement there consisted of

repeated requests from an informant posing as

a fellow recovering addict who had fallen off

the wagon.

[Sherman v. United States, 356

U.S. 369, 371 (1958).] In Jacobson the Court

found entrapment as a matter of law . . . the

inducement in that case was a two-year

campaign

of

fake

mail-order

entreaties

conditioning the defendant to believe that

child porn was acceptable and encouraging him

to purchase it. [Jacobson v. United States,

503 U.S. 540, 546–47 (1992).]

. . . [In each of these cases] [t]he entrapment

defense was available because the government's

solicitation of the crime was accompanied by

subtle and persistent artifices and devices

that created a risk that an otherwise lawabiding person would take the bait.

Mayfield, 771 F.3d at 434 (emphasis added).

In sting operations, the Government should know when to

take "no" for an answer, lest, as here, the "Government's quest

for conviction leads to the apprehension of an otherwise lawabiding citizen who, if left to his own devices, likely would have

never run afoul of the law." Gendron, 18 F.3d at 961 (quoting

Jacobson, 503 U.S. at 553-54)(emphasis added in original).

I respectfully dissent.

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53

This is a copy of a public record, reproduced as it was published. It is not legal advice, and it may not be the version a court would rely on. Check the official source before you cite it.

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