Petition for Writ of Certiorari — Hugo Santana-Dones, Petitioner v. United States

No. _____

________________________________________________

In the

Supreme Court of the United States

October Term, 2018

_______________________________________________

HUGO SANTANA-DONES,

Petitioner,

v.

UNITED STATES OF AMERICA,

Respondent

________________________________________________________

PETITION FOR A WRIT OF CERTIORARI TO THE UNITED

STATES COURT OF APPEALS FOR THE FIRST CIRCUIT

______________________________________________________

PETITION FOR WRIT OF CERTIORARI

AND APPENDIX

___________________________________________________________

Karen A. Pickett

Pickett Law Offices, P.C.

Counsel of Record

125 High Street, 26th Floor

Boston, MA 02110

(617) 423-0485

Counsel for Hugo Santana-Dones

QUESTIONS PRESENTED

1. Whether This Court Should Grant This Petition Because The First Circuit’s Standard Of

Review On The “Necessity” Of A Warrant To Intercept Wire Communications Violates

Mr. Santana-Dones’ Constitutional And Statutory Rights And Finds No Support In Other

Circuits.

2. Whether This Court Should Grant This Petition Because The Government Did Not

Meet Its Statutory Burden Of Showing The Warrant To Intercept Wire Communications

Was “Necessary.”

ii

TABLE OF CONTENTS

QUESTIONS PRESENTED ............................................................................................... ii

TABLE OF CONTENTS ................................................................................................... iii

TABLE OF AUTHORITIES ............................................................................................. iv

OPINIONS BELOW ............................................................................................................1

JURISDICTION ..................................................................................................................1

RELEVANT CONSTITUTIONAL AND STATUTORY PROVISIONS ..........................2

STATEMENT OF CASE ....................................................................................................3

REASONS FOR GRANTING THE PETITION………………………………………… 6

A. This Court Should Grant The Petition Because A Standard Of Review As

To Whether A Wiretap Interception Is Necessary Should Not Be Based

On Whether Facts Set Forth In A Wiretap Application Were “Minimally

Adequate” - - This Standard Violates Mr. Santana-Dones’ Rights

And Does Not Find Support In Other Circuits………………………………..6

B. The First Circuit’s Opinion Does Not Establish That The Wiretap

Warrant Was Necessary……………………………………………………….8

CONCLUSION…………………………………………………………………………... 12

INDEX TO APPENDICES

Appendix A: Judgment and Opinion of the United States Court of Appeals ....................A

Appendix B: Finding and Order of the District Court ....................................................... B

iii

TABLE OF AUTHORITIES

Cases

United States v. Ashley, 876 F.2d 1069 (1st Cir. 1989)………………………………………11

United States v. Delima, 886 F.3d 64 (1st Cir. 2018)………………………………………...10

United States v. Giordano, 416 U.S. 505 (1974)………………………………………………8

United States v. Gordon, 871 F.3d 35 (1st Cir. 2017)………………………………………….7

United States v. Ippolito, 774 F.2d 1482 (9th Cir. 1985)…………………………………..9, 11

United States v. Lopez, 300 F.3d 46 (1st Cir. 2012)………………………………………….11

United States v. Melendez-Santiago, 644 F.3d 54 (1st Cir. 2011)……………………………10

United States v. Rodriguez, 851 F.3d 931 (9th Cir. 2017)……………………………………..8

United States v. Santana-Dones, 920 F.3d 70 (1st Cir. 2019)………………………………….7

Constitutional And Statutory Provisions

Fifth Amendment to the United States Constitution………………......................................2, 8

18 U.S.C. §2518…………………………………………………………………………..passim

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No. _____

________________________________________________

In the

Supreme Court of the United States

October Term, 2018

_______________________________________________

HUGO SANTANA-DONES,

Petitioner

v.

UNITED STATES OF AMERICA,

Respondent

________________________________________________________

PETITION FOR A WRIT OF CERTIORARI TO THE UNITED

STATES COURT OF APPEALS FOR THE FIRST CIRCUIT

______________________________________________________

Hugo Santana-Dones (“petitioner” or “Mr. Santana-Dones”) respectfully petitions this

Court for a writ of certiorari to review the judgment of the United States Court of Appeals for the

First Circuit that affirmed the judgment of the United States District Court for the District of

Massachusetts.

OPINIONS BELOW

The judgment and opinion of the United States Court of Appeals for the First Circuit is

Appendix A to this petition. The finding and order of the United States District Court of

Massachusetts denying Mr. Santana-Dones’ motion to suppress is attached as Exhibit B to this

petition.

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JURISDICTION

The Judgment of the United States Court of Appeals for the First Circuit was entered on

March 29, 2019. This Court has jurisdiction under 28 U.S.C. § 1254(1). The District Court had

jurisdiction pursuant to 18 U.S.C. § 3231, and the Court of Appeals had jurisdiction pursuant to

28 U.S.C. § 1291.

RELEVANT CONSTITUTIONAL AND STATUTORY PROVISIONS

18 U.S.C. Section 2518(3):

(3) Upon such application the judge may enter an ex parte order, as requested or as modified,

authorizing or approving interception of wire, oral, or electronic communications within the

territorial jurisdiction of the court in which the judge is sitting (and outside that jurisdiction but

within the United States in the case of a mobile interception device authorized by a Federal court

within such jurisdiction), if the judge determines on the basis of the facts submitted by the

applicant that—

(a)

there is probable cause for belief that an individual is committing, has committed, or is about to

commit a particular offense enumerated in section 2516 of this chapter;

(b)

there is probable cause for belief that particular communications concerning that offense will be

obtained through such interception;

(c)

normal investigative procedures have been tried and have failed or reasonably appear to be

unlikely to succeed if tried or to be too dangerous;

(d)

except as provided in subsection (11), there is probable cause for belief that the facilities from

which, or the place where, the wire, oral, or electronic communications are to be intercepted are

being used, or are about to be used, in connection with the commission of such offense, or are

leased to, listed in the name of, or commonly used by such person

Fifth Amendment To United States Constitution:

No person shall be held to answer for a capital, or otherwise infamous crime, unless on a

presentment or indictment of a grand jury, except in cases arising in the land or naval forces, or

in the militia, when in actual service in time of war or public danger; nor shall any person be

subject for the same offense to be twice put in jeopardy of life or limb; nor shall be compelled in

any criminal case to be a witness against himself, nor be deprived of life, liberty, or property,

without due process of law; nor shall private property be taken for public use, without just

compensation.

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STATEMENT OF THE CASE

A. Procedural History1

On September 16, 2015, the grand jury returned an indictment against Mr.

Santana-Dones and four co-defendants. (RA 17). Mr. Santana-Dones was charged with three

counts: conspiracy to possess with intent to distribute, and to distribute, heroin and cocaine in

violation of 21 U.S.C. § 846 (Count One); distribution and possession with the intent to

distribute heroin in violation of 21 U.S.C. § 841(a)(1) (Count Four); and possession of heroin

and cocaine with the intent to distribute in violation of 21 U.S.C. § 841(a)(1) (Count Eight). (RA

17-33).

On July 15, 2016, Mr. Santana-Dones and three of his co-defendants filed a “Motion to

Suppress Evidence Obtained by Unlawful Interception of Wire Communications” (hereafter

referred to as “Motion to Suppress”). (RA 34). The Government opposed this Motion. (RA

103). The district court held a non-evidentiary hearing on September 6, 2016. (RA 9; D.E. 75).

On October 11, 2016, the district court entered a finding and order denying the Motion to

Suppress. (RA 123; Add. 8-10).

Mr. Santana-Dones and the Government entered into a plea agreement on April 19, 2017.

(RA 126). Pursuant to the plea agreement: “Defendant’s plea shall, with the U.S. Attorney’s

consent, be a conditional plea of guilty, reserving Defendant’s right to appeal the denial of

Defendant’s Motion to suppress the wiretap evidence seized in this case…” On May 18, 2017,

Mr. Santana-Dones pleaded guilty pursuant to the terms of the plea agreement. (R.A. 12; D.E.

164). On September 6, 2017, Mr. Santana-Dones was sentenced to a term of imprisonment of 80

Matters contained in the Appendix at the First Circuit will be designated by RA-page

number.

1

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months. (RA 13; D.E. 184). Judgment entered on the docket on September 18, 2017 (RA 139),

and Mr. Santana-Dones filed a timely appeal that same day. (RA 146).

B. Facts Relevant To Resolution Of The Petition

The Government gathered evidence by means of a court-ordered authorization

to intercept wire communications to and from a telephone number that the Government claimed

was used by co-defendant Osvaldo Vazquez (“Mr. Vazquez”). (RA 53). The authorization was

based upon an April 2015 application to the court by DEA Special Agent Michael Boyle (“Agent

Boyle”). (RA 51-102).

In Mr. Santana-Dones’ Motion to Suppress, he asserted that the Government had not

established, as a prerequisite to intercepting wiretap communications under 18 U.S.C. §

2518(3)(c), that: “normal investigative procedures have been tried and failed or reasonably

appear to be unlikely to succeed if tried or to be too dangerous[.]” (RA 37). This assertion was

premised on the Affidavit of Agent Boyle that revealed that the Government indeed had

successfully utilized investigative procedures and did not show that the requested interceptions

were needed because of lack of success or danger. Mr. Santana-Dones asserted that the

intercepted communications should be suppressed pursuant to the Fourth Amendment and to 18

U.S.C. §2515 which requires suppression of evidence obtained in violation of the statutory

requirements for intercepted communications. (RA 34-35).

In the Affidavit, Agent Boyle averred that the investigation into the alleged drug

trafficking organization (“DTO”) began in the Spring of 2014 with an anonymous tip from a

confidential informant (Aff., paras. 22; 36, RA 61; 63). This confidential informant (“CS-1”)

told law enforcement that she had known Mr. Vazquez “approximately 5 or more years

previously” and believed him to be a “heroin trafficker.” (Aff., para. 22, RA 61). Upon

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direction of law enforcement, CS-1 contacted Mr. Vazquez and renewed her relationship with

him. (Aff., par 22, RA 61).

As detailed in Agent Boyle’s Affidavit, law enforcement had great success utilizing CS1. CS-1’s continuing cooperation resulted in numerous controlled buys, incriminating audio and

video recordings, and the gathering of a plethora of information about the inner workings of the

alleged DTO. (Aff., paras. 36-65, RA 63-73).

Law enforcement was able to gain immediate access to Mr. Vazquez and the alleged

DTO through the informant. CS-1 was able to set up meetings at will, and there was no

indication that any defendant ever refused to meet with her. (Aff., paras 36-65, RA 63-73). The

meetings resulted in five successful controlled buys from August 2014 – March 2015, and

included the successful retrieval of heroin. (Aff., paras. 40-43; 45-47; 51-53; 54-60; 63-65, RA

64-73). Even in an instance where Mr. Vazquez appeared to observe police surveillance, law

enforcement was still able to complete a controlled buy. (Aff., para 92, RA 85-86).

Throughout the course of the investigation, Mr. Vazquez disclosed the identities of

additional alleged DTO participants to CS-1. Law enforcement observed CS-1 meet with Mr.

Vazquez and co-defendants Jose Lugo and Franshelly Alcantara in October 2015. (Aff., para 49,

RA 67). CS-1 was asked to take a management position within the DTO for the cities of

Lawrence and Marlboro. (Aff., para 49, RA 67).

In December 2014, CS-1 was invited to a location in Providence, Rhode Island with Mr.

Vazquez, Mr. Lugo and a man known as “Chaco.” (Aff., para. 56, RA 70). CS-1 was

encouraged to participate in the DTO and was asked if she would be willing to “transport large

sums of currency for [the DTO].” (Aff., para 57; RA 70). At that meeting, she was further taken

to the basement and shown two kilograms of heroin. (Aff., para 58, RA 70).

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CS-1 also received the personal cellular phone number of another alleged DTO

participant, Ortega Sanabria. (Aff., para 67(b), RA 74). CS-1 further was in communication

with Mr. Santana-Dones and introduced a second confidential informant to him. (Aff., para 31,

RA 62).

In his summary of the investigative efforts, Agent Boyle asserted that during the course

of the investigation, “[A]gents have, among other things: (a) gathered information from

confidential sources and informants; (b) conducted physical surveillance; (c) attached and

monitored court-authorized GPS tracking devices used by [Mr. Vazquez]; (d) issued

administrative subpoenas for telephone, rental car and travel records; (e) analyzed phone records

and pen register data.” (Aff., para 70, RA 76).

Despite the investigative successes and the lack of detection of surveillance by members

of the alleged DTO, Agent Boyle claimed that wiretap communications needed to be intercepted

to discover, e.g., the roles of the alleged DTO members, the alleged DTO’s source(s) of supply

and the methods by which the alleged DTO collected and laundered drug proceeds. (Aff., para

71, RA 77) Agent Boyle stated that he did not believe law enforcement could gain more traction

from the confidential informants because they were working as customers of the alleged DTOs,

and unlikely to receive information about the source of supply, the methods of delivery and the

larger distribution network of the alleged DTO. (Aff., paras. 77-78, RA 79).

REASONS FOR GRANTING THE PETITION

This Court should grant the petition because an appellate standard of review as to

whether a wiretap application is “minimally adequate” does not comport with statutory or due

process commands, and is inconsistent with standards of review used in other circuits. The

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Court also should grant the petition because the application here failed to meet the statutory

requirement of “necessity” justifying the interceptions.

A. This Court Should Grant The Petition Because A Standard Of Review As To Whether

A Wiretap Interception Is Necessary Should Not Be Based On Whether Facts Set

Forth In A Wiretap Application Were “Minimally Adequate” - - This Standard

Violates Mr. Santana-Dones’ Rights And Does Not Find Support In Other Circuits

Pursuant to 18 U.S.C. § 2518(3)(c), a judge may enter an order allowing

interception of wire, oral or electronic communications, only if she “determines on the basis of

the facts submitted by the applicant that --….normal investigative procedures have been tried and

have failed or reasonably appear to be unlikely to succeed if tried or to be too dangerous…” The

applicant “should demonstrate that the government has made a reasonable, good faith effort to

run the gamut of normal investigative procedures before resorting to means as intrusive as

electronic interception of phone calls.” United States v. Gordon, 871 F.3d 35, 46 (1st Cir. 2017).

The First Circuit erred in applying a standard of review that lessened the Government’s

statutory burden to establish necessity. It held that the “pivotal question” on review is “whether

the facts set forth in the application were minimally adequate to support the determination that

was made.” United States v. Santana-Dones, 920 F.3d 70, 75 (1st Cir. 2019) (internal quotations

and citation omitted).

As an initial matter, the standard of “minimal adequacy” used by the First Circuit does

not appear to have been established or adopted by any other circuit. Recently, the Ninth Circuit

discussed its standard of review of a district court’s order as: “we determine de novo whether

the information in an affiant's application for a wiretap amounts to a full and complete statement

as to whether or not other investigative procedures have been tried and failed or why they

reasonably appear to be unlikely to succeed if tried or to be too dangerous. If the wiretap

application meets the requirements of § 2518(1)(c), then the Court reviews for abuse of

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discretion the issuing court's finding that the wiretap was necessary under § 2518(3)(c) and its

decision to grant the wiretap.” United States v. Rodriguez, 851 F.3d 931, 937 (9th Cir. 2017)

(internal quotations and citations omitted). Applying a “minimally adequate” review standard

does not comport with a requirement of a first-step de novo review of the application.

Moreover, whether or not a wiretap warrant is “necessary” as required by section 2518 is

a legal determination subject to de novo review and not by deciding whether a district court’s

decision is “minimally adequate.” Applying the “minimally adequate” standard of review

further does not comport with Mr. Santana-Dones’ Fifth Amendment due process rights because

it relieves the Government of its statutory burden of showing “necessity.” See United States v.

Giordano, 416 U.S. 505, 515 (1974) (statute allowing wire interceptions “imposes important

preconditions” and should be used “with restraint;” the “applicant must state and the court must

find that normal investigative procedures have been tried and failed or reasonably appear to be

unlikely to succeed if tried or to be too dangerous.”)

B. The First Circuit’s Opinion Does Not Establish That The Wiretap Warrant Was

Necessary

The First Circuit’s opinion that the wiretap warrant was “necessary” violated Mr.

Santana-Dones’ rights and cannot be sustained. Here, the necessity requirement was not met

upon any review of Agent Boyle’s Affidavit.

Reading Agent Boyle’s Affidavit a whole establishes that the government had great

investigative success by traditional investigative means including utilizing: confidential

informants, surveillance, numerous controlled buys, GPS tracking, and pen registers. Indeed,

CS-1 was a highly trusted member of the alleged DTO who was encouraged to join in a

managerial capacity. Moreover, no controlled buy was halted due to suspected surveillance.

The Government had more than enough “goods” to pursue criminal prosecution but instead

8

wanted to get to bigger fish by shortcutting normal and productive investigative techniques. This

Court should grant the petition to remedy the violation of Mr. Santana-Dones’ privacy rights in

this manner. See United States v. Ippolito, 774 F.2d 1482, 1486 (9th Cir. 1985) (government

should not be able to “ignore avenues of investigation that appear both fruitful and costeffective”…court “would flout the statutory intent that wiretaps be used only if necessary, were

we to sanction a wiretap simply because the government pursued some ‘normal’ investigative

strategies that were unproductive, when other more fruitful investigative methods were

available.”).

In contrast to the detailed listing of the Government’s investigative successes in Agent

Boyle’s affidavit, the “necessity” showing is premised on speculation and boilerplate recitation

of standards. For example, Agent Boyle states simply that “[n]ormal investigative procedures

have been tried and have failed, appear unlikely to succeed if tried, or are too dangerous to

employ…” (Aff., para 11, RA 55). But it is abundantly clear from the rest of the Affidavit that

CS-1 had never been in danger from the other alleged DTO members - - in fact, they were

looking to “promote” her to a managerial capacity to deal drugs in specific territories and to

transport large sums of proceeds.

The Affidavit also asserts in boilerplate fashion that the wiretap was necessary because it

was “the only available investigative technique …which has a reasonable likelihood of revealing

and securing admissible evidence needed to establish the full scope and nature of the Target

Offenses and the full scope and nature of the VAZQUEZ DTO, the Target Subjects, and their

criminal associates.” (Aff., para 68, RA 75). Unclear is how this can be the “only” investigative

technique in light of the extensive evidence unearthed by law enforcement. Moreover, the

Affidavit never establishes with any logic why law enforcement refused to allow CS-1 to further

9

infiltrate the alleged DTO. Although the district court found that being a confidential informant

is “dangerous work,” there was no evidence that CS-1 faced any present or future danger from

the alleged DTO so as to justify interceptions of private phone conversations.

The facts as presented in Agent Boyle’s Affidavit are in stark contrast to other cases

where courts have upheld the necessity of the interception of communications. For example, in

Gordon, the court noted that “at least one confidential source ad been outed because the source

had been sold fake (or extremely low-quality) heroin in executing a controlled buy.” 871 F.3d at

46, n. 3. In United States v. Melendez-Santiago, 644 F.3d 54, 57 (1st Cir. 2011), agents had not

been successful in infiltrating the alleged organization, and at the time of the wiretap application,

“one of the confidential sources had been missing for months and was presumed dead; another

had been threatened with death and was no longer trusted by members of the organization.” In

United States v. Delima, 886 F.3d 64, 70 (1st Cir. 2018), the court upheld the order authorizing a

wiretap where the CIs were “low level ‘runners’ who did not have access to information

pertinent to the investigation’s goals.”

Unlike these cases, at the time of the wiretap application here, it was clear that CS-1 was

a trusted member of the alleged DTO and was asked to assume a managerial role in dealing

drugs and transporting money that would have allowed investigators even more information.

Her cooperation along with other normal investigative techniques rendered the application to

intercept communications here not necessary.

In addition to failing to establish that the normal investigative techniques that had been

used or could be used had failed, the Government also did not establish that they were “too

dangerous” pursuant to section 2518(3)(c). The claim of danger in Agent Boyle’s Affidavit was

mere boilerplate and unlike other cases where facts set forth by the Government established

10

danger. For example, in United States v. Ashley, 876 F.2d 1069, 1076 (1st Cir. 1989), a

codefendant named D’Alessio: “on two occasions warned one of the agents that he would kill

him or harm his family if he discovered that the agent was in fact a law enforcement officer. On

another occasion, D'Alessio checked the agent to determine if he was wearing a tape recorder.

D'Alessio again accused the agents of being ‘feds’ during another meeting and a companion of

D'Alessio was observed noting the license plate number of the agents' vehicle…” See also

United States v. Lopez, 300 F.3d 46, 54 (1st Cir. 2002) (affidavit alleged that the organization

was becoming aware of law enforcement involvement and a cooperator was “questioned by

conspiracy members as to whether he was in league with the authorities.”) In this case, there

simply was no showing that either law enforcement or the cooperating witnesses were in harm’s

way to justify the invasion of privacy that occurred.

In short, there can be no doubt that intercepting communications here may make law

enforcement’s job easier and more efficient. But Congress clearly placed a necessity

requirement on interception of communications to protect the proliferation of using these

intrusive means in lieu of standard and effective investigative techniques. See, e.g., Ippolito, 774

F.2d at 1486 (where law enforcement has other, fruitful investigative means, it cannot resort to

seeking a wiretap which is a “serious intrusion”). Although Agent Boyle’s affidavit is quite

long, reading it as a whole in fact establishes that without the interception, the investigation was

successful and promised to be even more so with the further use of CS-1 in the investigation and

the continued use of surveillance, GPS tracking and pen register reviews. There was no

indication that continuing these efforts would prove “too dangerous.” In short, the application to

intercept communications failed to establish the necessity of the intrusion as required under 18

U.S.C. § 2518(3)(c). This Court should grant this petition because if the First Circuit’s decision

11

is upheld, there really is no substance to Congress’ requirement that applications for warrants to

intercept wire communications show “necessity.”

Finally, this appeal was consolidated with the appeals of other co-defendants. Pursuant

to Fed.R.App.P. 28(i), to the extent that Mr. Santana-Dones’ co-defendants have submitted or

will submit petitions to this Court and raise relevant and helpful points, Mr. Santana-Dones joins

in those points as well.

CONCLUSION

For the reasons set forth above, Mr. Santana-Dones respectfully requests that this Court

grant his petition for a writ of certiorari.

Respectfully submitted,

HUGO SANTANA-DONES

By his counsel,

/s/Karen A. Pickett

_____________________________

Karen A. Pickett

Pickett Law Offices, P.C.

Counsel of Record

125 High Street, 26th Floor

Boston, MA 02110

(617) 423-0485

kpickettlaw@gmail.com

Dated: June 27, 2019

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