United States v. Pineda-Buenaventura

In the

United States Court of Appeals

For the Seventh Circuit

Nos. 09-1500, 09-1525, 09-1875 & 09-2431

U NITED S TATES OF A MERICA,

Plaintiff-Appellee,

v.

T EODULO P INEDA-B UENAVENTURA ,

O TONIEL M ENDOZA, G ERARDO P INEDA-SORIA, and

A RTURO P INEDA-L OPEZ,

Defendants-Appellants.

Appeals from the United States District Court

for the Western District of Wisconsin.

No. 08-CR-105—Barbara B. Crabb, Judge.

A RGUED M ARCH 31, 2010—D ECIDED S EPTEMBER 15, 2010

Before M ANION and W ILLIAMS, Circuit Judges, and

D ARRAH, District Judge.Œ

W ILLIAMS, Circuit Judge. This is a consolidated appeal

of four defendants involved in a large cocaine distribu-

Œ

The Honorable John W. Darrah, United States District Court

for the Northern District of Illinois, Eastern Division, sitting

by designation.

2 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

tion conspiracy that operated in Jefferson County, Wis-

consin. Following an investigation involving wiretap

surveillance, controlled purchases, and confidential in-

formants, sixteen individuals were charged in two

separate indictments for conduct related to the conspir-

acy. The four defendants involved here—Teodulo Pineda-

Buenaventura, Otoniel Mendoza, Gerardo Pineda-Soria,

and Arturo Pineda-Lopez—each pled guilty to pos-

sessing or conspiring to possess with intent to distribute

cocaine. Each now appeals. Teodulo Pineda-Buenaventura

challenges his sentence, arguing that the drug amount

calculation in his presentence investigation report was

insufficient to support the statutory mandatory mini-

mum sentence he received. Otoniel Mendoza challenges

the validity of his guilty plea, arguing that his plea col-

loquy did not satisfy the requirements of Federal

Rule of Criminal Procedure 11. Gerardo Pineda-Soria

appeals the denial of his motion to suppress drugs

found in his apartment and statements he made there-

after, arguing that the search violated the Fourth Amend-

ment. And Arturo Pineda-Lopez’s attorney has filed an

Anders brief, seeking to withdraw on the basis that there

are no non-frivolous arguments to be made by Pineda-

Lopez on appeal.

For the reasons explained below, we vacate Pineda-

Buenaventura’s sentence and remand for resentencing

because the district court’s drug quantity findings

did not support the sentence he received. We also

vacate Mendoza’s conviction because his plea colloquy

did not satisfy the requirements of Rule 11, and so we

remand for further proceedings. Furthermore, we affirm

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 3

the district court’s denial of Pineda-Soria’s motion to

suppress because he and his co-tenants gave valid

consent to search his apartment. Finally, we grant

Pineda-Lopez’s counsel permission to withdraw because

a challenge to the reasonableness of his sentence would

be frivolous.

I. TEODULO PINEDA-BUENAVENTURA—DRUG

AMOUNT FINDING

Teodulo Pineda-Buenaventura was a “runner” in the

drug conspiracy who delivered cocaine at the direc-

tion of his cousin, Efrain Pineda-Buenaventura, one of

the co-leaders of the conspiracy.1 On June 19, 2008, after

wiretap surveillance, police executed a search warrant

at his home and recovered cocaine, a digital scale, a

firearm, and $16,000 in cash. He was arrested, admitted

to his involvement in the conspiracy, and on Decem-

ber 10, 2008, pled guilty pursuant to a written plea agree-

ment to a single count of conspiracy to possess with

intent to distribute at least 500 grams of cocaine. The

plea agreement provided that he was subject to a

60-month mandatory minimum term of imprisonment

pursuant to 21 U.S.C. § 841(b)(1)(B), but offered no

details as to the specific amount of drugs to which he

was admitting responsibility. At the plea hearing, the

1

“Pineda-Buenaventura” refers to defendant-appellant Teodulo

Pineda-Buenaventura. When we refer to Efrain Pineda-

Buenaventura, we do so using his full name so as to avoid

confusion.

4 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

government acknowledged that while the count to

which Pineda-Buenaventura was pleading was based

on an amount of at least 500 grams, if the presentence

investigation resulted in a finding that he was re-

sponsible for less, he would only be held accountable

for that lower amount.

Pineda-Buenaventura’s presentence investigation re-

port (“PSR”) stated that 105 grams of cocaine were re-

covered from his home during the execution of the

search warrant and that wiretap surveillance showed

he had made deliveries totaling approximately 300

grams of cocaine. The PSR also found that Pineda-

Buenaventura made 22 additional deliveries in which

the drug quantities “could not be determined.” Based on

these findings, the PSR stated that “[t]he probation

office believes that Teodulo’s relevant conduct involves

at least 400 grams to 500 grams of cocaine, resulting in

a base offense level of 24. This is a conservative estimate.”

At Pineda-Buenaventura’s sentencing hearing, the

district judge imposed the statutory minimum sentence

of 60 months based on responsibility for 500 or more

grams of cocaine. The district court appeared to agree

with the findings in the PSR—including, presumably,

its estimate that Pineda-Buenaventura was responsible

for “at least” 400 to 500 grams of cocaine—but then

stated “[y]our relevant conduct involves at least 400

grams but less than 500 grams of cocaine.” (emphasis

added). Apparently, the district judge believed that

Pineda-Buenaventura was responsible for at least 500

grams (given that she sentenced him to a mandatory

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 5

minimum based on that amount), but then made an

express finding that he was responsible for less than

that amount.

Pineda-Buenaventura contends that his PSR does not

establish that he was responsible for at least 500 grams of

cocaine in the conspiracy, the amount necessary for the

charge to which he pled. Because he forfeited this argu-

ment by failing to challenge the PSR’s amount deter-

minations below (he admits this), the sentence is re-

viewed for plain error.2 United States v. Jacques, 345 F.3d

960, 962 (7th Cir. 2003). Under this standard of review,

we affirm a sentence unless, after considering all the

evidence, we have a “definite and firm conviction that

a mistake has been committed.” United States v. Haynes,

582 F.3d 686, 709 (7th Cir. 2009) (quotation omitted).

We find that while the PSR may support a finding that

Pineda-Buenaventura was responsible for at least 500

grams under the evidentiary standards applicable at

sentencing, remand is necessary because the sentencing

judge made a finding on the record that Pineda-

Buenaventura was responsible for less than that amount.

2

The government argues that Pineda-Buenaventura waived,

not merely forfeited, appeal on this issue. But waiver is an

intentional, strategic decision not to raise a challenge, whereas

an argument is forfeited when the issue is not raised neg-

ligently or accidentally. See United States v. Cooper, 243 F.3d

411, 416 (7th Cir. 2001). We can discern no tactical reason

behind Pineda-Buenaventura’s failure to raise this argument.

See United States v. Jaimes-Jaimes, 406 F.3d 845, 848 (7th Cir.

2005) (“Waiver principles should be construed liberally in

favor of the defendant.”).

6 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

Evidentiary standards at sentencing are not as

stringent as those at trial. United States v. Taylor, 72

F.3d 533, 543 (7th Cir. 1995). A district court can deter-

mine drug quantities attributable to a defendant based

only on a preponderance of the evidence, United States

v. Salinas, 62 F.3d 855, 859 (7th Cir. 1995), and can rely

on the findings set forth in a PSR so long as the infor-

mation has “sufficient indicia of reliability to support

its probable accuracy.” U.S.S.G. § 6A1.3(a). That said, we

have encouraged courts to “make conservative estimates

[of drug amounts], especially when presented with gen-

eralized testimony, as a way to . . . approximate drug

quantities.” United States v. Henderson, 58 F.3d 1145,

1152 (7th Cir. 1995). Here, while the facts set forth

in Pineda-Buenaventura’s PSR would arguably support

a finding that he was responsible for over 500 grams of

cocaine under the standard we just described, the sen-

tencing judge’s express statement that his relevant

conduct involved “less than 500 grams” forecloses any

such interpretation and compels remand.

“A sentencing based on an incorrect Guidelines range

constitutes plain error and warrants a remand for

resentencing, unless we have reason to believe that the

error in no way affected the district court’s selection of

a particular sentence.” United States v. Farmer, 543 F.3d

363, 375 (7th Cir. 2008). Here, relevant conduct in-

volving an amount between 400 and 499 grams—the

amount expressly referenced by the district judge—

would have generated an advisory Guideline range of

46-57 months, not the 60-month minimum set forth

in § 841(b)(1).

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 7

Remand will provide the district court with an oppor-

tunity to clarify its findings regarding the drug amount

attributable to Pineda-Buenaventura and to impose

an appropriate sentence for that amount. See, e.g., United

States v. Salem, 597 F.3d 877, 887-88 (7th Cir. 2010) (re-

manding for resentencing when findings were insuf-

ficient to support sentence imposed). It is possible that

the sentencing judge merely misspoke when making

the finding that Pineda-Buenaventura’s relevant conduct

involved “less than 500 grams,” but there is no way to

be sure of this, especially when the PSR on its own

terms does not unequivocally establish that Pineda-

Buenaventura was responsible for at least 500 grams

of drugs. See id. at 888 (if court relies on PSR to make a

finding as to certain conduct, the PSR must actually

define that conduct); see also Farmer, 543 F.3d at 375 (“We

have no reason to believe that the district court would

not have selected an even lower sentence if given the

opportunity to do so, thus, we must remand.”).

II. OTONIEL MENDOZA—RULE 11 PLEA COLLO-

QUY

Otoniel Mendoza was another “runner” that delivered

cocaine in the conspiracy. A search warrant executed

at Mendoza’s home yielded 339 grams of cocaine and

9 grams of methamphetamine. Wiretap surveillance

revealed that he had delivered an additional 283 grams

of cocaine, and made 21 additional deliveries for which

the amount could not be determined. On December 12,

2008, Mendoza pled guilty to a single count of conspiracy

8 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

to possess at least 500 grams of cocaine with intent to

distribute, pursuant to a written plea agreement. The

agreement stated that he was subject to a 60-month man-

datory minimum term of imprisonment per 21 U.S.C.

§ 846, but did not discuss any relevant conduct to which

he was pleading.

Mendoza makes two arguments on appeal: (1) that

his plea colloquy did not satisfy Rule 11’s requirement

that his plea be knowing and voluntary, and (2) that the

facts upon which his mandatory minimum sentence

was based must be found by a jury. We address each in

turn.

A. Mendoza’s Plea Colloquy Did Not Satisfy Rule 11

Mendoza claims that his guilty plea to conspiring to

distribute cocaine fell short of Rule 11’s requirement

that it be knowing and voluntary. He argues that the

district court failed to ensure that he understood the

nature of the conspiracy charge to which he was

pleading, that he never clearly pled guilty to specific acts

in furtherance of that conspiracy, and that he was never

clearly told he was pleading to an offense with a five-

year mandatory minimum sentence.

A careful review of Mendoza’s colloquy with the court

at his plea hearing—relevant portions of which we

quote below—demonstrates that Mendoza was indeed

confused with the concept of the conspiracy to which

he was pleading, and was equivocal in many of his an-

swers to the court regarding his conduct. We cannot

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 9

say with confidence that Mendoza ever truly under-

stood the nature of the conspiracy to which he was ad-

mitting involvement, nor can we determine exactly

what acts Mendoza believed he was admitting to. We

conclude that the plea colloquy fell short of Rule

11(b)(1)(G)’s requirement that Mendoza understand

the nature of the charge to which he pled guilty.

1. The Plea Colloquy

Problems began early in Mendoza’s exchange with

the court, which took place through a translator due

to Mendoza’s limited English. Asked by the district

judge whether he understood that the government was

charging him with agreeing with others to distribute

drugs, he answered “Yes. But the one thing about us

coming to an agreement isn’t so”—displaying a lack of

agreement with a critical element of a conspiracy.

Noticing Mendoza’s apparent confusion, the district

court attempted to clarify Mendoza’s understanding of

the conspiracy, and the following exchange occurred:

THE COURT: When you talk about a conspiracy,

it’s not saying that you all sat around a table and

agreed on each and every part of the conspiracy.

The Government has to show that you did agree

to something that carried out the conspiracy. The

Government says that this conspiracy involved

cocaine and it involved at least 500 grams of co-

caine. That doesn’t—the Government isn’t saying

that you yourself were responsible for dis-

tributing 500 grams, but it does say that the con-

10 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

spiracy, all of the people involved conspired to

distribute 500 grams or more.

MENDOZA: I just have one question.

THE COURT: Yes.

MENDOZA: Could you tell me more or less

how many people are in the conspiracy?

THE COURT: According to the Indictment, there’s

seven that are named. That includes you, but

then the Indictment also talks about others who

may or may not be known to the grand jury.

MENDOZA: Well, the thing is that I wasn’t in

contact with those people. I don’t know those

people, and I can’t name them here in the papers.

The district judge again attempted to clarify by explaining

that Mendoza need not have specifically reached agree-

ment with each member of the conspiracy, to which

he vaguely replied “[w]ell, maybe I’m pleading guilty

because I did sell a few times.” When the court at-

tempted to again determine whether Mendoza under-

stood the government’s allegations as to what he had

done, Mendoza’s answer was still equivocal: “Yes, I do

understand, but I need to see a little bit more. I don’t

know how much the Government may have.”

Later in the hearing, the government proffered some of

the evidence it would have introduced had Mendoza

chosen to go to trial. The government referred to inter-

cepted telephone calls between Mendoza and Efrain

Pineda-Buenaventura in which Mendoza was directed to

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 11

deliver cocaine; Mendoza’s own admission at the time

of his arrest that he had delivered cocaine; and evidence

that had been seized at Mendoza’s apartment, including

200 grams of cocaine, a digital scale, and packaging

materials. Asked whether he disputed any of the evi-

dence the government said it could prove, Mendoza

said that he did not.

Mendoza was then asked to describe in his own

words what he had done in connection with the con-

spiracy, however, and this is where things again got

problematic. Mendoza began by vaguely describing

his relationship with Efrain Pineda-Buenaventura, but

did not initially describe any activity involving the

delivery of cocaine. The court sought to focus matters

and the following exchange ensued:

THE COURT: Did you—did you deliver drugs

to [Efrain] Pineda-Buenaventura? Did you pick up

drugs from him?

MENDOZA: No.

THE COURT: Did you do any of the things that

Mr. Connell [government lawyer] talked about?

MENDOZA: I don’t remember too well what it

was that he said, but—

The government lawyer then offered to assist by re-

iterating some of the government’s proof against

Mendoza, which the court invited him to do. The gov-

ernment lawyer again referred to intercepted telephone

calls in which Efrain Pineda-Buenaventura instructed

12 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

Mendoza to deliver drugs to various persons, and also

again referred to Mendoza’s own statement at his arrest

that he had in fact delivered drugs at Efrain Pineda-

Buenaventura’s direction. When the court turned back

to Mendoza and sought to confirm his understanding of

this, this exchange occurred, which we quote at length:

THE COURT: Did [Efrain] Pineda-Buenaventura

call you and ask you or tell you to deliver drugs?

MENDOZA: He told me to go and deliver some

CDs that some people had lent to him.

THE COURT: All right. I’m not going any farther

with this. Mr. Mendoza, if you don’t agree that you

did any of the things that Mr. Connell says you

did, we’ll continue this trial—this for trial.

MENDOZA: Well, there is a part that I am guilty of

there, but the thing is though in part they are

pinning a lot of stuff on me and I don’t believe

I did all of that.

THE COURT: All right. I’ll start—I’ll give you one

last chance and then I have other matters that

I need to take care of, Mr. Mendoza, and I’m not

interested in spending more time with you if

you’re not willing to take any responsibility. We’ll

just go to trial. We’ll have a jury decide what

happened in this case. I’ll ask you once again, did

you deliver any cocaine at the request of any of

the people that you conspired with? Mr. Delyea

[defense counsel].

DEFENSE COUNSEL: Actually the point I made

is did you ever just do it one time. Apparently

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 13

there were times when they delivered CDs and

DVDs.

THE COURT: I’m not interested in that.

DEFENSE COUNSEL: I understand.

THE COURT: I just want to know whether he

ever delivered cocaine.

DEFENSE COUNSEL: If there was ever one occa-

sion.

THE COURT: Ever. Any occasion on which he

delivered cocaine with any of the people named

in the Indictment or others.

MENDOZA: Yes, there was one time. But not

specifically in the calls, but one time, yes.

THE COURT: And who called you and asked you

to deliver cocaine?

MENDOZA: Well, it wasn’t directly—it wasn’t

directly somebody calling me and saying well,

let’s deliver cocaine to so-and-so. I think it was

cocaine—well, I never had this, but I think it

was cocaine.

THE COURT: But who asked you to deliver it?

MENDOZA: Well they called me and had

me—Efrain called me to have me take that over to

someone who I guess had ordered it from him.

I don’t know how they ordered the stuff from him.

THE COURT: You don’t need to know that. Who

called you? [Efrain] Pineda-Buenaventura?

14 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

MENDOZA: Yes, him.

THE COURT: All right. Then on the basis of this

extended discussion with counsel and with

Mr. Mendoza and upon the basis of the entire

record in the case, I find and conclude,

Mr. Mendoza, that you have entered a plea of

guilty knowingly, understandingly, and volun-

tarily . . . .

2. Analysis

Mendoza claims that his plea colloquy did not comply

with Rule 11 because he never understood the nature of

the charge against him. Because Mendoza never sought

to withdraw his plea in the district court, our review is

for plain error. United States v. Vonn, 535 U.S. 55, 63

(2002); United States v. Burnside, 588 F.3d 511, 520

(7th Cir. 2009). We review Mendoza’s claim of a

Rule 11 violation to determine whether (1) an error has

occurred; (2) it was plain; (3) it affected Mendoza’s sub-

stantial rights; and (4) it seriously affected the fair-

ness, integrity, or public reputation of the judicial pro-

ceedings. See Burnside, 588 F.3d at 520.

Rule 11 requires that “before the court accepts a plea

of guilty or nolo contendere . . . the court must address

the defendant personally in open court . . . [and] inform

the defendant of, and determine that the defendant

understands . . . the nature of each charge to which

the defendant is pleading.” Fed. R. Crim. P. 11(b)(1)(G). It

requires that a district court “ensure that [the defendant]

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 15

understands the law of his crime in relation to the facts

of his case.” Vonn, 535 U.S. at 62. Unless a defendant

“fully comprehends the elements of the crime to which

he is confessing, his plea cannot be said to have been

knowingly and voluntarily entered.” United States v.

Fernandez, 205 F.3d 1020, 1025 (7th Cir. 2000) (quota-

tion and citation omitted). To determine whether a de-

fendant in fact understands the nature of a charge, we

take a totality-of-the-circumstances approach and con-

sider (1) the complexity of the charge; (2) the de-

fendant’s intelligence, age, and education; (3) whether

the defendant was represented by counsel; (4) the

district judge’s inquiry during the plea hearing and the

defendant’s own statements; and (5) the evidence

proffered by the government. Id. (citing United States

v. LeDonne, 21 F.3d 1418, 1423 (7th Cir. 1994)).

Our assessment of these factors in Fernandez is instruc-

tive here. In Fernandez, a native Spanish-speaking defen-

dant with a fifth grade education and limited English

pled guilty to conspiring to distribute marijuana. 205

F.3d at 1022. At his plea hearing, Fernandez, like

Mendoza here, demonstrated confusion both with the

concept of the conspiracy and the specific acts to which

he was pleading guilty. Id. at 1025-27. In his exchanges

with the court, Fernandez gave ambiguous, partial, and

even contradictory answers, and at times appeared con-

fused. Id. For example, when asked by the court whether

he had done the things set forth in the government’s

proffer, Fernandez gave inconsistent and unclear

answers, varying from “Yes, your Honor, I did,” to “[n]ot

16 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

everything. I thought I was pleading guilty partially,” to

“[n]ot all of the acts, partially.” Id. at 1026-27.

On appeal, Fernandez argued his plea was not

voluntary, and we agreed, finding the guilty plea

to have been “enveloped in confusion and misunder-

standing.” Id. at 1026. Reviewing the record, we found

that Fernandez exhibited confusion over the nature of

the conspiracy, and that “like most lay people, Fernandez

would not understand the term ‘conspiracy’ without

some further explanation.” Id. at 1026. We also found

that there was general confusion regarding “precisely

what acts Fernandez admitted.” Id. at 1027. We con-

cluded that “Fernandez’ accounts of what acts he ad-

mitted and those he denied were very murky. Based

on this record, it is impossible to ascertain precisely

what acts Fernandez admits and which he denies.” Id.

Evaluating the totality of the circumstances, we held

that “we cannot conclude that Fernandez was fully

aware of the nature of the crime to which he pleaded

guilty” and remanded the case to the district court for

a new plea. Id. at 1026, 1030.

Reviewing the record here (especially the portions

quoted above) in light of Fernandez and the relevant

factors, we cannot say with confidence that Mendoza

ever truly understood the nature of the conspiracy to

which he was pleading. Mendoza demonstrated confu-

sion with the concept of the conspiracy, and that confu-

sion was never fully resolved by the court. Nor can we

clearly determine exactly what acts Mendoza admitted.

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 17

The first two factors in our totality-of-the-circumstances

approach—complexity of the charge and defendant’s

age and education—mitigate against a finding that

Mendoza understood exactly what he was pleading to.

Conspiracy is not a concept immediately under-

standable to a layperson. See United States v. Blalock, 321

F.3d 686, 689 (7th Cir. 2003) (“[C]onspiracy is generally

considered a rather complicated offense.”); see also United

States v. Wetterlin, 583 F.2d 346, 350 (7th Cir. 1978) (charge

of conspiracy “is not a self-explanatory legal term”). The

relative complexity of a conspiracy charge, coupled

with Mendoza’s sixth-grade education level and lim-

ited English, favor a finding that Mendoza did not com-

prehend the charge to which he was pleading. See

Fernandez, 205 F.3d at 1026.

The fact that Mendoza was represented by counsel—

the third factor in our inquiry—did not alleviate the

problems we perceive here. At certain points during the

plea hearing, Mendoza’s lawyer did attempt to clarify

matters for his client and the court, but those attempts

are not a substitute for Mendoza himself actually indi-

cating an understanding of the charge to which he was

pleading. At certain points during the hearing, counsel’s

presence almost seems to have complicated matters—

at times when meaningful follow-up questions might

have confirmed Mendoza’s understanding, counsel

instead stepped in and offered comments that took the

court in another direction. Moreover, Mendoza himself

indicated at the beginning of the hearing that there had

been some communication problems with his lawyer.

Asked by the court whether counsel had answered all of

18 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

his questions, Mendoza answered, “Well, I’m not really

clear on some of them, but others, yes.” Mendoza in-

dicated that he was not sure if his lawyer had understood

him in their conversations, stating that “[h]e doesn’t

speak my Spanish.” And counsel himself informed the

court at the close of the plea hearing that he and

Mendoza had had “some difficulty communicating.”

The fourth factor—the district judge’s inquiry during

the plea hearing and the defendant’s own statements—

is the most troubling. A careful review of the plea

colloquy demonstrates that Mendoza never seemed

to have a real grasp of what the conspiracy was. The

court made attempts to clarify and explain the con-

spiracy to Mendoza, but the record shows that he at

best indicated only partial understanding, and at times

made statements that entirely undercut it—such as “the

one thing about us coming to an agreement isn’t so”

and “I wasn’t in contact with those people.” Further

attempts were made to clarify matters, to which

Mendoza only stated that he would “need to see a little

bit more” in order to understand, because he didn’t

“know how much the Government may have.”

And when it came time for Mendoza to explain in

his own words what he did, his accounts were

noncommital, vague, and evasive. Mendoza repeatedly

hedged in his answers and descriptions of his conduct

to the court, prompting numerous (fruitless) clarifying

questions from the court. At one point, he even dis-

cussed delivering compact discs for Efrain Pineda-

Buenaventura instead of drugs. Eventually, after signifi-

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 19

cant back-and-forth with the court —during which time

the district judge told Mendoza that he had “one last

chance,” that she had “other matters . . . to take care of,”

and that “I’m not interested in spending more time with

you if you’re not willing to take any responsibility”—

Mendoza finally stated that Efrain Pineda-Buenaventura

had on one occasion instructed him to deliver drugs to

someone. This lone statement is eclipsed in context by

the significant confusion that preceded it. At any point

during the colloquy, the district court could have taken

a brief recess in order to allow counsel to talk with his

client confidentially, address Mendoza’s apparent con-

fusion, and determine if he did indeed wish to proceed

with a plea. Such a conference might have helped to

avoid the problems that occurred here. But based on this

record, we cannot be confident that Mendoza under-

stood the nature of the crime to which he was pleading

guilty, or exactly which acts he was admitting having

committed. See Fernandez, 205 F.3d at 1027. The fourth

factor in our totality-of-the-circumstances inquiry favors

Mendoza.

The fifth factor in our inquiry examines the govern-

ment’s proffered evidence. Examining this factor in

Fernandez, we found that “while there was nothing

wrong with the AUSA’s factual proffer on its face, the

surrounding chaos at this change of plea hearing sig-

nificantly negated any confidence in Fernandez’ under-

standing of and admission to those facts.” Id. The same

could be said here. The government’s explanation of its

evidence against Mendoza was sufficient, but Mendoza’s

20 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

various reactions to it undermine our confidence that

he understood the acts to which he was admitting. While

Mendoza initially said that what the government had

proffered was “fair,” he then later stated that he did not

remember what the government’s evidence was. Even

when the proffer was reiterated, he showed further

confusion and was evasive. Just as in Fernandez, where

we were concerned with a defendant who admitted to,

in his words, “[n]ot all of the acts, partially,” here Mendoza

was similarly noncommital, saying “there is a part that

I am guilty of there, but the thing is . . . I don’t believe

I did all of that.” See id. (“Because we cannot glean a

clear understanding of Fernandez’ participation in the

crime charged, it is impossible to determine whether

Fernandez himself understood the nature of the crime

to which he was pleading guilty.”). Mendoza’s tentative,

qualified responses to the government’s proffered evi-

dence undermine our confidence that he really did under-

stand exactly what to which he was pleading guilty. See id.

We find that the Rule 11 errors that occurred during the

plea colloquy in this case were plain and affected

Mendoza’s substantial rights. See Vonn, 535 U.S. at 62;

see also United States v. Bradley, 381 F.3d 641, 647 (7th Cir.

2004) (“Misunderstanding of the nature of the charge . . .

is not harmless error.”). That a plea be knowing and

voluntary is a “core concern” of Rule 11. United States v.

Pena, 314 F.3d 1152, 1157 (9th Cir. 2003). “[A] defendant’s

clear understanding of the nature of the charge to which

he is pleading guilty relates to the very heart of the

protections afforded by the Constitution and Rule 11.”

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 21

Fernandez, 205 F.3d at 1027. Looking at the totality of

the circumstances, we conclude that the variances from

Rule 11 that occurred during Mendoza’s plea colloquy

warrant vacatur of his conviction and a remand for

further proceedings.3

3

Mendoza also argues that his plea was not knowing and

voluntary because he did not have a clear understanding of the

mandatory minimum sentence he faced and that he never

actually pled guilty to responsibility for the requisite 500

grams or more of drugs to support that sentence. Because

we vacate the plea on other grounds, we need not reach this

argument. We note, however, that in this respect “Rule 11 only

requires that the court inform the defendant of the maximum

and minimum penalties . . . as well as the fact that the partic-

ular sentence imposed will be determined by reference to the

federal sentencing guidelines.” Blalock, 321 F.3d at 689 (holding

that plea was voluntary when court had not determined

drug amount at time of hearing, and told defendant amount

would be subsequently determined); see also Fed. R. Crim. P.

11(b)(1)(I). That requirement was satisfied here. The govern-

ment specifically referred to the potential five-year mandatory

minimum at the hearing, and Mendoza’s lawyer himself

clarified with the court that the drug amount was not being

established at that hearing, and instead would occur later

when the PSR was written. See, e.g., United States v. Wagner,

996 F.2d 906, 912 (7th Cir. 1993) (rejecting claim that plea

was involuntary on basis that specific amount had not been

determined, noting that parties had acknowledged exact drug

amounts would be calculated later).

22 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

B. Whether Facts Triggering Mendoza’s Mandatory

Minimum Sentence Needed to Be Proven Beyond

a Reasonable Doubt

Mendoza also appeals his sentence on the basis that a

jury, not a sentencing court, must find facts sufficient to

trigger the application of the mandatory minimum sen-

tence to which he was subjected. Because we are va-

cating Mendoza’s conviction on the basis set forth above,

we need not reach this issue. We note, however, that this

argument is foreclosed in the Seventh Circuit, because

our precedent is clear that judges may determine drug

amounts by a preponderance of the evidence that sub-

ject a defendant to a statutory mandatory minimum. See,

e.g., United States v. Clark, 538 F.3d 803, 811-12 (7th

Cir. 2008); United States v. Price, 516 F.3d 597, 605 (7th

Cir. 2008). Mendoza acknowledges this, but states in his

brief that he raises the issue to “preserve it for further

review” in light of the Supreme Court having granted

certiorari in United States v. O’Brien, 560 U.S. - - - -, 130

S. Ct. 2169 (2010) (the case has been decided since the time

Mendoza filed his brief). It is unclear why Mendoza

hedged a bet on the outcome of O’Brien. O’Brien

involved a provision of 18 U.S.C. § 924(c)—a statute not

at issue in this case—that provides for a 30-year man-

datory minimum sentence when the firearm used in

the offense is a machine gun. 18 U.S.C. § 924(c)(1)(B)(ii).

The O’Brien court ruled that the fact that a gun is a ma-

chine gun is an element of the § 924(c) offense that

must be proved to a jury beyond a reasonable doubt, as

opposed to a sentencing factor to be proven to the judge.

O’Brien, 130 S. Ct. at 2180. The holding has no bearing

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 23

on the validity of Mendoza’s sentence under 21 U.S.C.

§ 841(b)(1)(B). As we have repeatedly held, the amount

of drugs a defendant possessed is not an element of a

§ 841 offense and the sentencing judge can find facts

that trigger a mandatory minimum sentence. See Clark,

538 F.3d at 811-12; see also United States v. Washington, 558

F.3d 716, 720 (7th Cir. 2009); Price, 516 F.3d at 605.

Amount findings need be determined beyond a rea-

sonable doubt only when they implicate a statutory

maximum prison term, which is not the case here. See

United States v. Kelly, 519 F.3d 355, 363 (7th Cir. 2008);

see also Harris v. United States, 536 U.S. 545 (2002).

III. GERARDO PINEDA-SORIA—MOTION TO SUP-

PRESS

Gerardo Pineda-Soria was a supplier of cocaine to the

conspiracy. He pled guilty to possessing with intent

to distribute cocaine in violation of 21 U.S.C. § 841(a),

subject to a plea agreement in which he retained his

ability to appeal the district court’s denial of his mo-

tion to suppress drugs that had been found during a

search of his residence. He was sentenced to 30 months’

imprisonment. He now appeals the denial of his motion

to suppress.

When considering a motion to suppress, we review the

district court’s legal conclusions de novo, and factual

findings and credibility determinations for clear error.

United States v. Lewis, 608 F.3d 996, 999 (7th Cir. 2010). We

are particularly deferential to credibility findings, and

“unless the trial court has credited testimony that is

24 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

contrary to the laws of nature or so internally incon-

sistent or implausible on its fact that no reasonable

factfinder would credit it, we defer to the trial court’s

finding.” United States v. Collins, 604 F.3d 481, 486 (7th Cir.

2010).

A. The Search of Pineda-Soria’s Apartment

On June 18, 2008, Drug Enforcement Agency (“DEA”)

agents obtained a search warrant for Pineda-Soria’s

residence at 253 South High Street, Apartment A, in

Janesville, Wisconsin. The doorway of 253 South High

Street opens into a two-story foyer, and the building is

divided into two apartments, A and B. The entrance to

Apartment A is on the first floor, and an open staircase

leads up to the door for Apartment B. Neither door has

a letter, however, so it would not necessarily be clear

to someone that they were separate apartments. Based

on information that the upstairs apartment was empty,

agents limited their warrant application only to Apart-

ment A, and the warrant itself was similarly limited. An

arrest warrant for Pineda-Soria was issued at the same

time.

At 6:01 a.m. the next morning, DEA agents and Janes-

ville police officers executed the warrant. None of the

DEA agents that were aware of the Apartment A/B dis-

tinction were present at the search, and apparently had

not informed any of the searching officers that the

warrant was limited to the downstairs unit. Unaware of

the warrant’s limitation or the distinction between the

units, the entry team entered both Apartments A and B. In

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 25

performing a preliminary sweep of Apartment B, agents

found three men sleeping: Pineda-Soria, along with

Hoguer Pineda and Adrian Lazcano (the “co-tenants”). The

three were taken downstairs and outside. Pineda-Soria

was taken to the Janesville police station to be inter-

viewed, while Pineda and Lazcano remained on the

premises.

Before any contraband was found, a DEA agent

became aware that Apartment B was a separate unit

after speaking with residents of the downstairs unit.

Realizing the error, searching officers immediately

ceased the nascent search and withdrew to the front

lawn to wait for further instructions. It was decided to

ask Pineda-Soria and the co-tenants for consent to

search, and DEA agents also contacted an Assistant

United States Attorney regarding the possibility of ob-

taining another search warrant for Apartment B at the

same time.

At approximately 6:45 a.m., a Spanish-speaking Janes-

ville police officer asked each co-tenant separately

whether he would consent to a search of Apartment B.

Both men had by this point been allowed to get

dressed, and were not handcuffed. The interviewing

officer first asked the co-tenants if they lived in the

unit and both stated that they did. The officer then

told them it was up to them whether or not to allow a

search and both individually gave oral consent to

search. Police decided it would be advisable to also

obtain written consent from each co-tenant, and tele-

phoned another officer to bring a written consent form

26 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

that he could translate into Spanish for them to read

and sign.

In the meantime, at the Janesville police station, DEA

agents and police advised Pineda-Soria of his rights

and asked for his cooperation. He signed a Miranda

waiver form, and at 7:08 a.m. he filled out a written

consent form consenting to a search of Apartment B.

The record is not clear as to whether officers resumed

searching the upstairs unit once the co-tenants consented

at 6:45 a.m., or whether they also waited for Pineda-

Soria’s consent that came approximately 25 minutes

later. In any event, officers re-entered Apartment B, and

found a kilogram of cocaine under Pineda-Soria’s bed.4

By this time, agents had completed an initial inter-

view with Pineda-Soria, who had to that point denied

any involvement in the alleged conspiracy. When they

brought him back to the apartment building, they

learned that cocaine had been found in the search of

Apartment B. This update was shared with Pineda-Soria,

and he was reminded of his Miranda rights. Pineda-Soria

agreed to cooperate, and confronted with the evidence

that had been found, admitted to involvement in the

conspiracy.

Pineda-Soria moved to suppress the physical evidence

found in his apartment and the statements that he had

made, arguing that the search of Apartment B occurred

4

At some point during the search, a Spanish translation of

a written consent form was produced for the co-tenants,

which each signed at 7:40 a.m.

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 27

without a valid warrant and that there had been no

valid consent, and on December 8, 2008, an evidentiary

hearing was held. On February 11, 2009, a magistrate

judge issued a Report and Recommendation that the

district court deny the motion to suppress, finding

(1) that the consents to search Apartment B were valid,

and (2) that the inevitable discovery doctrine also ap-

plied. On March 5, 2009, the district court adopted the

Report and Recommendation and denied the motion to

suppress. Pineda-Soria then entered into a conditional

plea to one count of possessing with intent to distribute

cocaine, reserving his right to appeal the denial of his

motion to suppress.

B. Whether the Consents Were Voluntary

Pineda-Soria appeals the denial of his motion to sup-

press on two grounds. First, he argues that none of the

consents given to search Apartment B were voluntary.

Second, he asserts that the inevitable discovery doc-

trine should not apply, arguing that the government

failed to meet its burden of proof to benefit from

that doctrine.

No one disputes that the initial search of the upstairs

unit was illegal; officers entered Apartment B armed with

a warrant that only gave them permission to search

Apartment A. Nothing was found in the brief initial

sweep, however. It was not until officers re-entered the

unit, after receiving consent to do so, that contraband

was discovered. The Fourth Amendment’s warrant re-

28 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

quirement does not apply in circumstances where an

authorized party voluntarily consents to a search. United

States v. Parker, 469 F.3d 1074, 1077 (7th Cir. 2007); see

also Schneckloth v. Bustamonte, 412 U.S. 218, 219 (1973).

The relevant question here is whether the consents

from Pineda-Soria and his co-tenants to search Apart-

ment B were valid.5

Whether a defendant voluntarily consented to a search

is a question of fact determined by examining the

totality of the circumstances. Lewis, 608 F.3d at 999. In

making this determination, we consider (1) the de-

fendant’s age, intelligence, and education; (2) whether

the defendant was advised of his constitutional rights;

(3) how long the defendant was detained prior to

giving consent; (4) whether the consent was immediate,

or was prompted by repeated requests by authorities;

(5) whether any physical coercion was used; and

(6) whether the defendant was in police custody when

he gave his consent. United States v. Risner, 593 F.3d

692, 694 (7th Cir. 2010); see also United States v. Figueroa-

Espana, 511 F.3d 696, 704-05 (7th Cir. 2007). We review

5

While none of the officers on the scene were aware of the

warrant’s limitation to Apartment A, under the collective

knowledge doctrine the fact that some DEA agents were aware

of the distinction forecloses the good faith exception here. See

United States v. Harris, 585 F.3d 394, 400 (7th Cir. 2009). We

agree with the district court’s conclusion that the DEA’s

failure to properly inform or supervise the executing police

of this fact was reckless, meaning the exclusionary rule is in

play. Herring v. United States, 129 S. Ct. 695, 702 (2009).

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 29

a district court’s finding of voluntary consent for clear

error. United States v. Santiago, 428 F.3d 699, 704 (7th Cir.

2007). And when consent is given after an illegal search

has occurred, we must also be sure that the illegality

did not taint any consent that was given. To determine

whether the taint from an initial illegal search has been

purged, we examine (1) the temporal proximity of the

illegal entry and the consent; (2) the presence of inter-

vening circumstances; and (3) the purpose and flagrancy

of the official misconduct. Brown v. Illinois, 422 U.S. 590,

603-04 (1975); see also United States v. Robeles-Ortega, 348

F.3d 679, 681 (7th Cir. 2003). Viewing the circumstances

in light of these standards, we find that the consents

given in this case were valid and were not tainted by

the initial warrantless search, and that the district court

properly denied Pineda-Soria’s motion to suppress.

1. The Co-Tenants’ Consents

We first examine the consents given by the co-tenants,

Pineda and Lazcano. Approximately 45 minutes tran-

spired between the time that they were rousted out of

bed to when they gave their initial oral consent. They

were permitted to get dressed, initially sat on a couch

in Apartment A, then were relocated to the yard outside

of the house. They were not handcuffed, and were in

the company of other people that they knew. The record

is not clear on their age or education level, but we know

that officers communicated with them in their native

Spanish. When asked for consent, both co-tenants were

informed that they did not have to give permission, both

30 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

orally and on the written consent forms they signed. See

United States v. Valencia, 913 F.2d 378, 381 (7th Cir.

1990) (finding it significant that defendant had been

told he did not have to consent to search). The record

shows that each man gave his consent immediately, and

there is no evidence of repeated prodding or questioning

by police. While being awoken by armed officers and

made to leave their dwelling certainly must have been

an intimidating experience, there is no evidence that

any subsequent events took place that were coercive in

any way.

Nor do we think that the initial illegal entry tainted

the co-tenants’ consent in any way. Considering the

Brown factors, we find that the temporal proximity of

the illegal entry and consent, taken together with the in-

tervening circumstances, support the district court’s

finding that there was no taint. Brown, 422 U.S. at 603-04.

Forty-five minutes transpired between the time of the

illegal entry and the co-tenants’ verbal consents, and an

hour and forty minutes passed between the entry and

the written consent. See Valencia, 913 F.2d at 382. There

is no evidence of any coercion taking place during that

time; conversely, both Pineda and Lazcano were told

they did not have to consent if they did not want to.

Finally, consideration of the “purpose and flagrancy

of the official misconduct” weighs heavily in favor of

finding that any taint was purged. The initial entry into

Apartment B was a mistake on the part of the searching

officers, none of whom were aware of the limitation

on the warrant. Once the mistake was discovered, officers

immediately withdrew from the upstairs unit to deter-

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 31

mine what should be done next. The initial entry does not

appear to have been at all flagrant or purposeful, and it

did not taint the co-tenants’ subsequent consent. The

district court’s determination that the co-tenants’ con-

sents were voluntary is not clearly erroneous.

Pineda-Soria contends that even if the consents were

voluntary, neither co-tenant had any authority to actually

give it. By failing to object to the magistrate judge’s rec-

ommendation finding that they had authority, Pineda-

Soria has waived this issue on appeal. United States v.

Moore, 563 F.3d 583, 585 (7th Cir. 2009). And in any

event, the co-tenants did have apparent authority to

consent to the search. A police officer asked both men, in

Spanish, if they lived in the unit, and both answered

that they did. Pineda-Soria argues that officers have a

duty to inquire further as to a third party’s authority,

but that is only true when the circumstances make the

authority questionable in the first place. See United States v.

Goins, 437 F.3d 644, 649 (7th Cir. 2006). An officer can

conduct a search when the facts available at the time

“warrant a man of reasonable caution in the belief that the

consenting party had authority over the premises.” Illinois

v. Rodriguez, 497 U.S. 177, 188 (1990) (quotation omit-

ted). Here, the facts clearly warranted such a belief.

Pineda and Lazcano had authority to grant consent to

search Apartment B.

2. Pineda-Soria’s Consent

Having reached this conclusion, we need not address

the voluntariness of Pineda-Soria’s consent, but do so

32 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

anyway. We are more concerned with the voluntariness

of Pineda-Soria’s consent than we are with that of the

co-tenants. He was rousted out of bed and whisked

away to a police station for interrogation, and was thus

in a far more restrictive and potentially coercive setting

than the co-tenants were. And unlike the co-tenants,

Pineda-Soria was not on the premises and had no knowl-

edge of what was transpiring there. For all Pineda-

Soria knew, contraband could already have been found

at the location, and he may well have felt pressure to

appear cooperative and consent when he otherwise

would not have. See, e.g., Brown, 422 U.S. at 605 n.12. At

the same time, he was given Miranda warnings, spoken

to in his native Spanish, and chose to sign a written

consent form agreeing to the search. While the question

of the voluntariness of Pineda-Soria’s consent is a closer

call than that of his co-tenants, we are not “left with the

definite and firm conviction that a mistake has been

made” by the district court, and we find no clear

error in its finding that Pineda-Soria’s consent was also

voluntary. Lewis, 608 F.3d at 1000 (quotation and citation

omitted).

Having found that the district court did not err in con-

cluding that the consents from Pineda-Soria and the co-

tenants were valid, we need not reach the question of

whether the inevitable discovery doctrine would also

have justified the warrantless search. See United States v.

Patterson, 65 F.3d 68, 72 (7th Cir. 1995). We affirm

the district court’s denial of Pineda-Soria’s motion to

suppress the contraband found in his apartment and

the statements he made in connection therewith.

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 33

IV. ARTURO PINEDA-LOPEZ—COUNSEL’S MO-

TION TO WITHDRAW

Arturo Pineda-Lopez was another “runner” in the con-

spiracy and was overheard on wiretaps delivering

cocaine for Efrain Pineda-Buenaventura. Evidence

showed he delivered somewhere between 500 grams and

2 kilograms of drugs. He pled guilty pursuant to a

plea agreement to conspiracy to possess with intent

to distribute 500 grams of cocaine, in violation of 21

U.S.C. § 846. Pineda-Lopez’s PSR determined that he

had a base offense level under the sentencing guidelines

of 21, after a 3-level downward adjustment based on

acceptance of responsibility and a 2-level downward

adjustment because he met the “safety valve” provision,

18 U.S.C. § 3553(f). Coupled with a criminal history

category of I, Pineda-Lopez’s advisory guideline range

was 37-46 months. At sentencing, the district court gave

him the bottom of the range: 37 months. Pineda-Lopez’s

trial counsel has filed an Anders brief seeking permission

to withdraw on the basis that there are no non-

frivolous arguments to be made on appeal. See Anders v.

California, 386 U.S. 738 (1967).

Pineda-Lopez did not respond to his counsel’s submis-

sion, and so we review the potential issues counsel has

identified in his brief. See United States v. Garcia, 580

F.3d 528, 543 (7th Cir. 2009). Counsel represents that

Pineda-Lopez would challenge the reasonableness of

his sentence by arguing that his 37-month term is

unduly harsh in light of his limited involvement in the

conspiracy and his lack of criminal history. Counsel

34 Nos. 09-1500, 09-1525, 09-1875 & 09-2431

claims that while Pineda-Lopez may view the sentence

as harsh, it was well within the district court’s discretion

to impose it, and points out that the sentence is at

the bottom of the advisory guideline range. Therefore,

counsel argues, Pineda-Lopez’s argument would be

frivolous if raised on appeal.

Having reviewed the record and counsel’s Anders brief,

we agree. The court reviews the reasonableness of a

sentence under an abuse of discretion standard. United

States v. Poetz, 582 F.3d 835, 837 (7th Cir. 2009). We

apply a presumption of reasonableness to a sentence

that reflects proper application of the guidelines. Rita v.

United States, 551 U.S. 338, 347 (2007). Here, the sentence

was reasonable. The district court properly calculated

and considered the applicable Sentencing Guidelines

range, did not clearly err in its factual findings, and

imposed a sentence at the bottom of the range after con-

sidering the § 3553(a) factors. We conclude that there

are no non-frivolous issues on appeal, grant coun-

sel’s motion to withdraw, and dismiss Pineda-Lopez’s

appeal. See United States v. Recendiz, 557 F.3d 511, 534 (7th

Cir. 2009).

CONCLUSION

We V ACATE Teodulo Pineda-Buenaventura’s sentence

and R EMAND to the district court for resentencing con-

sistent with this opinion. We V ACATE Otoniel Mendoza’s

conviction and R EMAND for further proceedings. We

A FFIRM the district court’s denial of Gerardo Pineda-

Nos. 09-1500, 09-1525, 09-1875 & 09-2431 35

Soria’s motion to suppress. And we G RANT Pineda-Lopez’s

counsel’s motion to withdraw and D ISMISS his appeal.

9-15-10