Petition for Writ of Certiorari — Nicholas Young, Petitioner v. United States

No. 18-__

IN THE

Supreme Court of the United States

____________________

NICHOLAS YOUNG,

Petitioner,

v.

UNITED STATES,

Respondent.

____________________

On Petition for a Writ of Certiorari

to the United States Court of Appeals

for the Fourth Circuit

____________________

PETITION FOR A WRIT OF CERTIORARI

____________________

David B. Smith

Counsel of Record

Nicholas David Smith

DAVID B. SMITH PLLC

7 East 20th Street, Suite 4R

New York, NY 10003

(917) 722-1096

nds@davidbsmithpllc.com

dbs@davidbsmithpllc.com

Counsel for Petitioner

i

QUESTIONS PRESENTED

The decision below affirmed Petitioner’s conviction

for attempting to provide material support to a Foreign Terrorist Organization (“FTO”) pursuant to 18

U.S.C. § 2339B. Following a six-year investigation,

Petitioner’s crime was to send $245 in gift cards to an

undercover agent, posing as an FTO member, who solicited them. During the former police officer’s entrapment trial, the district court admitted dozens of

white nationalism artifacts as evidence of Petitioner’s

predisposition to materially support militant Islamism and permitted an expert to educate the jury on a

perceived white nationalist-militant Islamic “convergence.” The government offered no evidence the FTO

seeks small financial contributions from Americans,

or that Petitioner ever considered making one prior to

the sting operation. The following questions are presented in this case:

1. Whether evidence of a criminal defendant’s

prior, constitutionally protected activity may be admitted to prove the predisposition element of the entrapment defense, and if so, whether such activity

must be “similar” in nature to the charged crime.

2. Whether, to avoid prosecution of thoughtcrime,

the predisposition element contains an objective “positional” component in addition to a subjective “dispositional” one. United States v. Hollingsworth, 27 F.3d

1196 (7th Cir. 1994) (en banc) (Posner, C.J.).

ii

TABLE OF CONTENTS

Page

PETITION FOR A WRIT OF CERTIORARI .............1

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

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

RELEVANT STATUTORY PROVISIONS.................1

STATEMENT OF THE CASE ....................................1

A. The Six-Year Undercover Investigation ...........3

B. Pretrial Proceedings and Trial .........................8

C. The Fourth Circuit’s Decision .........................11

REASONS FOR GRANTING THE WRIT................11

I. THE COURTS OF APPEALS ARE DIVIDED

OVER THE CONTOURS OF “PREDISPOSITION” EVIDENCE ..............................................13

A. Following Jacobson, the Second, Sixth,

Eighth and Ninth Circuits Only Permit

Predisposition Evidence of Prior Crimes .......13

B. The Fourth Circuit and Others Have Unwisely Split with Jacobson .............................15

II. THE COURTS OF APPEALS ARE DIVIDED

OVER WHETHER THE PREDISPOSITION

ELEMENT CONTAINS AN OBJECTIVE

“POSITIONAL” COMPONENT BEYOND

THE SUBJECTIVE “DISPOSITIONAL” ONE

..............................................................................19

iii

TABLE OF CONTENTS

(continued)

Page

A. The Seventh, First and Fifth Circuits

Require Proof the Defendant Was Objectively Positioned to Commit the

Crime Absent Government Intervention .............................................................19

B. The Second and Ninth Circuits, and the

District Court Here, Have Strayed

from Jacobson ...........................................23

CONCLUSION ..........................................................29

APPENDIX A:

Fourth Circuit Opinion

(February 21, 2019) ..............................................1a

APPENDIX B:

District Court Order Denying Rule 29(a) Motion

(December 15, 2017) ...........................................39a

APPENDIX C:

Statutory Provision Involved

18 U.S.C. § 2339B ...............................................43a

iv

TABLE OF AUTHORITIES

Page(s)

CASES

Brandenburg v. Ohio,

395 U.S. 444 (1969) ............................................ 16

Holder v. Humanitarian Law Project,

561 U.S. 1 (2010) ................................................ 25

Illinois v. Gates,

462 U.S. 213 (1983) ............................................ 20

Jacobson v. United States,

503 U.S. 540 (1992) ..................................... passim

Rayamajhi v. Whitaker,

912 F.3d 1241 (9th Cir. 2019)............................ 25

Sherman v. United States,

356 U.S. 369 (1958) ........................................ 3, 17

Sorrells v. United States,

287 U.S. 435 (1932) ............................................ 17

United States v. Barger,

931 F.2d 359 (6th Cir. 1991).............................. 16

United States v. Becker,

62 F.2d 1007 (2d Cir. 1933) ............................... 15

United States v. Blankenship,

775 F.2d 735 (6th Cir. 1985).............................. 14

United States v. Bramble,

641 F.2d 681 (9th Cir. 1981).............................. 14

United States v. Cromitie,

727 F.3d 194 (2d Cir. 2013) ..............14, 22, 23, 26

United States v. Gamache,

156 F.3d 1 (1st Cir. 1998) .................................. 22

United States v. Gendron,

18 F.3d 955 (1st Cir. 1993) ................................ 22

v

TABLE OF AUTHORITIES

(continued)

Page(s)

United States v. Harvey,

991 F.2d 981 (2d Cir. 1993) ............................... 14

United States v. Hollingsworth,

27 F.3d 1196 (7th Cir. 1994) (en banc)....... passim

United States v. Kaminski,

703 F.2d 1004 (7th Cir. 1983)...................... 15, 16

United States v. Khalil,

279 F.3d 358 (6th Cir. 2002).............................. 16

United States v. Lachapelle,

969 F.2d 632 (8th Cir. 1992).............................. 14

United States v. Mayfield,

771 F.3d 417 (7th Cir. 2014).............................. 22

United States v. McLaurin,

764 F.3d 372 (4th Cir. 2014).............................. 16

United States v. Reyes,

239 F.3d 722 (5th Cir. 2001).............................. 22

United States v. Russell,

411 U.S. 423 (1973) ........................................ 3, 17

United States v. Thickstun,

110 F.3d 1394 (9th Cir. 1997)............................ 23

United States v. Wise,

221 F.3d 140 (5th Cir. 2000).............................. 22

Zalaski v. City of Hartford,

723 F.3d 382 (2d Cir. 2013) ............................... 21

STATUTES AND RULES

18 U.S.C. § 2339B .................................................. 24

Fed. R. Evid. 401 ...................................................... 8

Fed. R. Evid. 403 ...................................................... 8

vi

TABLE OF AUTHORITIES

(continued)

Page(s)

Fed. R. Evid. 404 ...................................................... 8

OTHER AUTHORITIES

Eric Lichtblau, How an American Ended Up

Accused of Aiding ISIS with Gift Cards,

N.Y.TIMES, Jan. 29, 2017 at A15 ......................... 5

Human Rights Watch, Illusion of Justice:

Human Rights Abuses in US Terrorism

Prosecutions (2014) ............................................ 12

Jensen and LaFree, Final Report: Empirical

Assessment of Domestic Radicalization

(College Park, Md.: University of

Maryland, 2016) ............................................. 9, 10

LaFave, Israel, King, Kerr, Criminal

Procedure (4th ed. 2015) ............................. 18, 28

Norris and Grol-Prokopczyk, Estimating the

Prevalence of Entrapment in Post-9/11

Terrorism Cases, 105 Crim. L. &

Criminology (2015) ............................................ 12

Paul Marcus, The Entrapment Defense

(4th ed. 2009) .............................................. 15, 17

Simon Sebag Montefiore, Stalin: The Court of the

Red Tsar (Knopf 2007) ...................................... 16

PETITION FOR A WRIT OF CERTIORARI

Petitioner Nicholas Young respectfully requests a

writ of certiorari to review the judgment of the United

States Court of Appeals for the Fourth Circuit.

OPINIONS BELOW

The opinion of the Fourth Circuit is reported at

916 F.3d 368 and is reprinted in the Appendix to the

Petition (“App.”) at 1a-38a.

JURISDICTION

The court of appeals issued its decision on February 21, 2019. App. 1a. This Court has jurisdiction

under 28 U.S.C. § 1254(1).

RELEVANT STATUTORY PROVISIONS

The pertinent provision in the U.S. Code is reprinted at App. 43a.

STATEMENT OF THE CASE

Following a six-year undercover investigation, petitioner Nicholas Young was charged with attempting

to provide material support to an FTO after sending

$245 in Google Play gift cards to an undercover agent

who had requested them. Young had served with distinction in law enforcement for the entire investigation. Convicted at trial over his entrapment defense,

he is now serving a fifteen-year prison sentence.

At trial, the government offered no evidence that

Young had ever communicated with any person affiliated with an FTO in the real world, entertained any

plans to join an FTO, or ever contemplated materially

contributing to one prior to sending the gift cards in

2

this case. Nor did the government offer evidence that

Young ever planned, attempted to commit, participated in, or encouraged, any act of violence.

No real-world terrorist appeared in the investigation. The charge was simply that, after various undercover agents befriended Young for over half a decade, he was ultimately prevailed upon to send gift

cards to one of them after an agent pretended in 2016

to travel to Syria to join the Islamic State, otherwise

known as ISIS, a group that did not exist when

Young’s investigation began in 2010. No evidence

was offered that ISIS in fact requests, or has requested, Google gift cards or other small-donor financial contributions from Americans.

Young’s conviction was built on two legal errors,

reflecting splits among the courts of appeals on key

entrapment defense questions that have remained

unresolved for at least 25 years.

First, although Young was charged with attempting to support a militant Islamist terror group in the

Middle East, the district court allowed the government to show the jury over three dozen pieces of Nazi

and white supremacist “evidence”—including images

of burning crosses displayed to the jury in closing argument—to establish Young’s predisposition to commit the gift-card offense. The Fourth Circuit affirmed, holding the entrapment defense opens the evidentiary door to “a broad swath of evidence [] of the

defendant’s character”—criminal or otherwise. That

is inconsistent with the more surgical approach of the

Second, Sixth, Eighth and Ninth Circuits, as well as

with this Court’s decisions, which require predisposition evidence to consist of prior, similar criminal acts,

3

not just disreputable but constitutionally protected

behavior or beliefs. Jacobson v. United States, 503

U.S. 540 (1992); United States v. Russell, 411 U.S. 423

(1973); Sherman v. United States, 356 U.S. 369

(1958).

Second, the district court found the evidence sufficient to convict Young even though it was undisputed

the government offered no proof that ISIS (or another

FTO) in fact requests—or was likely to request—

small financial contributions from Americans, or that

Young had ever considered making one before sending the gift cards. That does not square with Jacobson’s cardinal holding that entrapment is “the apprehension of an otherwise law-abiding citizen who, left

to his own devices, likely would have never run afoul

of the law.” 503 U.S. at 553-54. The Court should clarify that—consistent with the interpretation of the

First, Fifth and Seventh Circuits—Jacobson demands

the government make a “positional” showing that, in

the totality of the objective circumstances, the crime

was of a sort the defendant likely would commit absent government intervention.

To avoid thoughtcrime prosecution, entrapment

cannot be merely a question of the defendant’s mental

state; it must also incorporate objective probability.

A. The Six-Year Undercover Investigation

From 2003 to the day of his arrest in August 2016,

Petitioner served as a Metro police officer in Washington, D.C. In 2006 the U.S. Attorney’s Office for the

District of Columbia awarded him a commendation

for subduing a robber brandishing a butcher’s knife,

without reaching for his police firearm. 4th Cir. Joint

4

Appendix (“CAJA”) at 1744-46. The following year, in

2007, Petitioner’s father died of myocardial infarction, bringing on Petitioner’s clinical depression.

Around the same time, he converted from Catholicism

to Islam. Id. at 1798-99.

In 2010 the FBI opened a counterterrorism investigation into Petitioner, code-named Slow Decline.

CAJA 1394. The predicate was Young’s “connection”

to a fellow George Mason University student who had

been arrested that year for attempting to provide material support to an FTO. However, the government

would later learn this “connection” consisted of a single phone call and mutual participation in the Muslim

Student Association at GMU. Id. at 513.

That same year, the Bureau tasked an undercover

agent with the pseudonym “Khalil Sullivan” to befriend Young and assess whether he posed a threat.

CAJA 509-11. Sullivan’s “legend”—his fictitious

background—was that he was a recent convert to Islam from Catholicism, as well as a U.S. Marine, both

of which traits would appeal to the patriotic Young,

who, horrified by the terror attacks on 9/11, had himself registered for the National Guard. Over nearly

two years, the government agent fabricated a friendship with Young, watching movies in Young’s home,

and praying with him in places of religious worship.

Id. at 504-13.

A questing personality led Young to travel the

world. Half a year after meeting Sullivan, in May

2011 Young ventured to Cairo, Egypt and, together

with a BBC reporter, across the border to Libya, then

in the midst of civil strife, with the U.S. Government

5

and its NATO allies giving material support to partisans contesting the rule of then-dictator Muammar

Qaddafi. CAJA 530-32. Young made no secret of traveling to Libya (later placing a bumper sticker on his

pickup truck unabashedly declaring, “Libya Civil War

Vet”), sharing the Government’s condemnation of

Qaddafian atrocities, encountering “migrant workers,

rebels, and humanitarian aid people,” and packing a

flak jacket, which he duly disclosed to customs agents.

Id. at 530-41. The sole documentary evidence of the

trip comprised photographs of Young riding a tourist’s

camel in the shadow of the pyramids, posing on the

beach with ordinary Libyans, and of children playing

with dogs. Id. at 1645-51; see also Eric Lichtblau,

How an American Ended Up Accused of Aiding ISIS

with Gift Cards, N.Y.TIMES, Jan. 29, 2017 at A15

(Young confiding to Lichtblau that although he got

“shot at a lot,” he didn’t join up with any terrorists).

After Young returned to the U.S. the same

month—May 2011—the Bureau took actions indicating it did not regard his Libya trip as a terrorism

threat. Agent “Sullivan” ceased investigating Young

in April 2012. CAJA 471. Shortly after his return,

the Bureau indicated it wished to recruit Young as a

paid informant. Id. at 1426-29. An internal Bureau

analysis determined (at “less than high confidence”)

that he had not traveled to Libya to join an FTO. Id.

at 1411-14. And when a Libyan national emailed

Young in June 2011 requesting a night-vision scope,

Young declined, noting it would be illegal under export laws. Id. at 1300-03. He remained on the police

force, carrying a firearm every day, for the next five

years.

6

Three years later, in May 2014, the Bureau paid

$34,000 to an informant with the pseudonym “Mo” to

befriend Young at a mosque and test again his willingness to support terrorism. CAJA 670-71. Young’s

“friendship” with the Bureau’s informant would continue for the next two years, through August 2016.

Id.

Mirroring Young’s own personal history, “Mo’s”

legend was that he attended GMU, had a religious

conflict at work and a strained relationship with his

father, and served in the military reserves. CAJA

567, 670. Over two years, Young and the FBI informant shared meals, prayed together, and held deeply

personal conversations about family and their love

lives (he had a weak point—this Fortunato). Id. at

714-16.

In summer of 2014, when ISIS emerged in Iraq,

Mo’s handler instructed him to broach the new terror

group with Young. CAJA 693. Among other remarks,

Young responded that ISIS were “a bunch of criminals

who are hungry for power and money”; that he was

“against ISIS because of all the bad stuff” he was

hearing about them; and that it was “un-Islamic to

rebel against the legitimate government.” Id. at 68485; 688-89. On the orders of his handler, Mo continued to press Young to support ISIS. When Mo indicated he wished to travel to Turkey, and perhaps then

on to Syria to join ISIS, Young admonished, inter alia,

that Mo should instead find a new job in America—

where Muslims are not restricted from practicing

their religion—and that joining an FTO was a crime.

Id. at 683, 692-94, 724-25.

7

Nevertheless, Young agreed to continue emailing

with Mo, even after the latter pretended to travel to

Turkey and then on to Syria. Then, for almost another two years, between December 2014 and August

2016, undercover agents posing as Mo sporadically

emailed Young “from Syria.” At this time, agents began acknowledging internally to one another that the

five-year-old investigation of Slow Decline was going

nowhere. Quipped one agent: nothing less than a “defibrillator” was needed to resurrect the investigation.

CAJA 1866-71.

At length, in July 2016 the agents posing as Mo

emailed and texted Young to send some Google Play

gift cards, putatively so the “brothers in Syria” could

purchase an encrypted chat app and communicate

with potential recruits outside Mesopotamia. (Google

Play gift cards can be redeemed for apps, podcasts,

movies and music retailed by Google.) After making

their solicitation, agents set forth the national security stakes of the Google card scheme as follows:

Agent A: “Let’s hope he goes 1 more step further.”

Agent B: “just 1 more step.”

Agent A: “1 huge step !!!!”

Agent B: “1 small step for [the counterterrorism

section], 1 giant leap for Slow Decline.” CAJA 1868

(email produced to the defense in classified format one

business day before the original trial date, together

with suggestion of the spoliation of multiple informant audio recordings of Petitioner).

Young ignored the agents’ first two attempts to solicit gift cards. On July 28, 2016, the agents asked

8

Young, for a third time, to send “any [gift card] codes

you can get. . . .” CAJA 855-58. This time Young sent

Google cards worth $245. A few days later, he was

arrested at his police station and charged with attempting to materially support the Islamic State.

B. Pretrial Proceedings and Trial

Young’s six-year probe never investigated a hate

crime; he had no criminal history. CAJA 1409. Accordingly, when agents searched his home following

his arrest in August 2016, it was pursuant to a warrant focused on evidence of FTO crimes, specifically

pertaining to ISIS. Id. at 55. The agents found no

evidence tying Young to any FTO.

Agents found something else. Entering a room

containing historical memorabilia from various world

wars and conflicts—Vietnam, Civil War, Crimean

War—agents spotted Nazi and white supremacist

posters, literature and curios. They placed a midsearch call to an Assistant United States Attorney,

asking how to proceed. The AUSA ordered the agents

to seize the Nazi “evidence.” CAJA 89-90.

Young indicated he would raise an entrapment defense, requiring the government to prove he had a

predisposition to give material support to an FTO

“prior to first being approached by government

agents,” Jacobson, 503 U.S. at 549—i.e., before 2010,

when agent “Sullivan” met Young—and four years before ISIS came into existence. The government conceded it could not satisfy the predisposition element

with evidence of Young’s proclivity for militant Islamism—it would need to offer the Nazi and white supremacist “evidence.” CAJA 114-15.

9

Denying Young’s pretrial objections under Rules

401, 403 and 404(b) of the Federal Rules of Evidence,

the district court allowed Nazi and white supremacist

evidence to be presented to the jury, predicating this

on a single comment Young had allegedly made fifteen years before trial. A fellow police officer “recalled” that, when they were both enrolled in a GMU

course entitled European Racism, they attended a

British National Party conference in 2001 for a class

project. Young was said to have remarked, “Do not

discount the idea of an alliance with the Muslims to

combat the Jews.” CAJA 139.

At the same time, the government proffered the

expert opinion of Dr. Daveed Gartenstein-Ross, the

owner of a for-profit national security consultancy.

Gartenstein-Ross proposed to testify that, in his expert opinion, there existed a white supremacist-militant Islamic “convergence.” His proposed testimony

included displaying for the jury dozens of Nazi, white

supremacist and anti-Semitic pictures and objects.

Gartenstein-Ross had never testified in a criminal

case or published any peer-reviewed papers on a Muslim-Nazi “convergence” (nor had any other person) or

on any ethnic nationalism subject. Before being engaged by the government, Gartenstein-Ross had undertaken no study to establish the “convergence,” nor

had any other researcher. Gartenstein-Ross was compensated $16,000 for his testimony.

The expert report omitted the findings of the country’s leading terrorism study, sponsored by the Department of Justice: Jensen and LaFree, Final Report: Empirical Assessment of Domestic Radicalization (College Park, Md.: University of Maryland,

10

2016) (the “EADR”). Having built the largest known

database on radicalization in the U.S., the EADR concluded:

(i) insufficient data exist to compare militant Islamist and far-right radicalization; but that,

(ii) initial indicators suggest dozens of material

distinctions in radicalization between the two groups.

EADR, p. 15.

In moving to exclude the “expert,” Young presented all this information to the district court. CAJA

154-72. Denying the motion, the district court: considered none of the Rule 702 factors; held no Daubert

hearing; and permitted no voir dire of the expert prior

to admitting his opinion. The court simply stated,

“he’s a better expert in some areas than others” and

admitted Gartenstein-Ross. CAJA 163-64.

At trial, the expert displayed for the jury over

three dozen pieces of white supremacist “evidence,”

including SS images, swastikas, pictures of Adolf Hitler, photographs of Young costumed as a Nazi for

World War II reenactment, Nazi history books, an

anti-Semitic cartoon. The government offered an Israeli flag seized from Young’s home, said to have been

disrespected by Petitioner. During closing argument,

a cross burned on each juror’s personal screen as an

AUSA averred that this evidence reflected Young’s

character. CAJA 1631-44. No evidence was offered

at trial that Young had ever considered materially

contributing to an FTO before the sting, or that ISIS

in fact seeks out financial contributions from Americans. The district court denied Young’s motion for

11

judgment of acquittal before submission to the jury.

App. 39a.

The jury found Young guilty of attempting to provide material support to the Islamic State. Making

no reference to ISIS or the gift cards—instead referencing his (nonexistent) “association” with white supremacists and his lawful ownership of firearms—the

district court delivered a sentence of fifteen years’ incarceration.

C. The Fourth Circuit’s Decision

The Fourth Circuit affirmed Young’s attempted

material-support conviction. App. 2a. (Separately, it

reversed Young’s two convictions for attempted obstruction of justice for insufficient evidence. Of the

four original charges filed against Young, three have

been dismissed or vacated on appeal for having been

supported by evidence insufficient for any rational juror to find guilt. Id. at 22a.)

Regarding predisposition evidence, the Fourth

Circuit, relying on pre-Jacobson precedent from the

Seventh Circuit, held that although white supremacism and militant Islamism are antithetical ideologies, the entrapment defense opens the door to, and

renders probative, “a broad swath of evidence [] of the

defendant’s character.” App. 11a. That distinguishes

the Fourth Circuit’s approach from that of the Second,

Sixth, Eighth and Ninth Circuits—and from this

Court’s precedent—which require that predisposition

proof consist of evidence the defendant previously

committed the same—or at least a similar—crime.

12

REASONS FOR GRANTING THE WRIT

The entrapment defense has long played a significant role in American criminal jurisprudence. But in

the aftermath of the September 11 terrorism attacks,

it has acquired new prominence in prosecutions involving the highest stakes in public policy. Since 9/11

over 800 individuals have been prosecuted in federal

courts for terrorism-related offenses. By some estimates, at least one of every three cases has been built

on a sting operation where an undercover agent

played an active role in the charged crime. Complicating matters further, the unbounded scope of activity swept up by terrorism “material support” statutes

has further muddied ambiguities in entrapment law.

See Human Rights Watch, Illusion of Justice: Human

Rights Abuses in US Terrorism Prosecutions 3 (2014)

(“Illusion

of

Justice”),

available

at

http://bit.ly/2VNhnck; see also Norris and Grol-Prokopczyk, Estimating the Prevalence of Entrapment in

Post-9/11 Terrorism Cases, 105 Crim. L. & Criminology 663 (2015) (database of post-9/11 sting operations

indicating approximately 5% of investigations

thwarted bona fide domestic security threats).

Yet the Court has not clarified entrapment doctrine in over 25 years. Jacobson v. United States, 503

U.S. 540 (1992). Since 1992, the courts of appeals

have divided in their interpretation of Jacobson along

two fundamental lines, both at issue here. First, they

disagree over the type of evidence the government

must offer to establish the defendant’s “predisposition” to commit the offense before the sting operation:

whether it must consist of a prior “similar” crime, or

13

merely of any derogatory information about the defendant’s character, constitutionally protected or no.

The courts of appeals are also split on another entrapment question: whether Jacobson requires a governmental showing not just that the defendant was

psychologically disposed to commit the offense, but

that he was also objectively positioned to commit it in

the totality of the circumstances. Courts hewing to

the latter interpretation reason that if entrapment exists to exculpate objectively harmless people—as Jacobson so holds—then predisposition law must be

drawn to exclude from penalty those who are unlikely

to commit the offense because of either their mental

disposition or lack of real-world opportunity.

The Court should use this case, which touches on

both these recurring questions arising in the post9/11 legal landscape, to settle them squarely.

I.

THE COURTS OF APPEALS ARE DIVIDED

OVER THE CONTOURS OF “PREDISPOSITION” EVIDENCE

A. Following Jacobson, the Second, Sixth,

Eighth and Ninth Circuits Only Permit

Predisposition Evidence of Prior Crimes

In Jacobson v. United States, the Court considered

a sting operation remarkably similar to this case, in

form if not criminal content. Federal agents began

investigating Jacobson when he purchased magazines

catering to an interest in preteen sex, though such periodicals were not then illegal to possess. For the next

two years—four fewer than here—the government

waged a campaign to lure Jacobson into buying magazines that, because they included photographs of

14

children engaged in sex, violated newly minted child

pornography laws. Agents advised Jacobson he would

be striking a blow for the First Amendment. He ultimately succumbed to the sting. 503 U.S. at 543-50.

Reversing his conviction, the Court clarified two

points of law relevant to this petition. First, “the prosecution must prove [] the defendant was disposed to

commit the criminal act prior to first being approached by government agents.” 503 U.S. at 549.

And, secondly, predisposition evidence may not consist of legal, constitutionally protected activity. That

is why Jacobson’s pre-investigation acquisition of legal but prurient magazines could not constitute predisposition evidence, for “evidence of predisposition to

do what once was lawful is not, by itself, sufficient to

show predisposition to do what is now illegal, for there

is a common understanding that most people obey the

law even when they disapprove of it.” Id. at 551.

The Second, Sixth, Eighth and Ninth Circuits

have kept faith with Jacobson’s holding that when the

government has induced the defendant to commit

crime X, in an entrapment trial his predisposition

must be proven with evidence of his prior conviction

of crime X, or at least by making a showing that he

committed prior crime X, or a crime “similar” to X. See

United States v. Harvey, 991 F. 2d 981, 996 (2d Cir.

1993) (citing Jacobson and reversing conviction for

predisposition-admission of legal, adult X-rated videotapes in child pornography trial); United States v.

Lachapelle, 969 F.2d 632, 638 (8th Cir. 1992) (in child

pornography case following Jacobson, district court

abused discretion by admitting predisposition evidence consisting of legally acquired pornography);

15

United States v. Blankenship, 775 F.2d 735, 739-40

(6th Cir. 1985) (in an illegal firearms dealing entrapment case, error to admit predisposition evidence consisting of defendant’s earlier discussion of purloining

a rare coin collection); United States v. Bramble, F.2d

681, 682-83 (9th Cir. 1981) (in cocaine distribution

sting trial, abuse of discretion for district court to admit predisposition evidence of defendant’s prior “cultivation of 21 marijuana plants”).

More recently, the Second Circuit addressed the

contours of predisposition evidence in the context of

militant Islamist terrorism. See United States v.

Cromitie, 727 F.3d 194, 207 (2d Cir. 2013). And although the panel’s majority opinion strayed from Jacobson in other respects (addressed infra), it nevertheless clearly held that predisposition evidence must

at least concern the defendant’s prior criminal activity, even if merely at the incipient “design” stage. 727

F.3d at 212 (citing defendant’s pre-investigation “designs” to: join a Pakistani terror group; buy missiles;

bomb someplace; take out an American plane: all

criminal activities); see also United States v. Becker,

62 F.2d 1007 (2d Cir. 1933) (Judge Hand focusing predisposition inquiry on “existing course of similar criminal conduct”) (emphasis added).

B. The Fourth Circuit and Others Have Unwisely Split with Jacobson

Prior to Jacobson, in United States v. Kaminski,

703 F.2d 1004, 1007 (7th Cir. 1983), the Seventh Circuit crafted a taxonomy of predisposition evidence.

Among other things, it held that the government may

offer predisposition proof showing the general “character and reputation of the defendant,” criminal or

16

otherwise. 703 F.2d at 1007. Although Kaminski preceded Jacobson, its inconsistent predisposition taxonomy—porous enough for the government to drive

through with a coach-and-four—has been widely followed by various federal appellate and hundreds of

trial courts. See Paul Marcus, The Entrapment Defense § 4.05D (4th ed. 2009) (collecting Kaminski-inspired federal and state cases).

Here, the Fourth Circuit followed Kaminski in lieu

of Jacobson. In a case concerning Petitioner’s alleged

support for a militant Islamist group in the Middle

East, the district court admitted over three dozen

pieces of “evidence” comprising SS images, swastikas,

pictures of Adolf Hitler, burning crosses, photographs

of Petitioner costumed as a Nazi for World War II

reenactment, Nazi history books, and anti-Semitic

cartoons. This “evidence” was not only not criminal

in nature, as required by Jacobson. It was also activity protected by the First Amendment, see, e.g., Brandenburg v. Ohio, 395 U.S. 444 (1969), as well as being

irrelevant to the crime charged, an attempt to provide

material support to an Islamist Foreign Terrorist Organization. 1 The Fourth Circuit affirmed the decision

to admit such “predisposition evidence” inasmuch as

the entrapment defense opens the door to “‘a broad

The exquisitely inflammatory irrelevance of this “evidence”

echoes an episode from the Moscow show trials in the 1930s. On

trial for his supposed terroristic support for a Rightist-Trotskyite convergence, the USSR announced that former KGB chief Yagoda’s dacha contained 3,904 pornographic images. Simon Sebag Montefiore, Stalin: The Court of the Red Tsar, p. 195 (Knopf

2007).

1

17

swath of evidence, including aspects of the defendant’s character….’” App. 11a. (quoting United States

v. McLaurin, 764 F.3d 372, 381 (4th Cir. 2014)). For

this predisposition-proof-may-comprise-general-character-evidence point of law, McLaurin in turn relies

on a Sixth Circuit decision. 764 F.3d at 381 (citing

United States v. Khalil, 279 F.3d 358, 365 (6th Cir.

2002)). Khalil in turn relies on United States v.

Barger, 931 F.2d 359 (6th Cir. 1991), which is itself

rooted in Kaminski. 931 F.2d at 366.

Inconsistent with Jacobson—and Rules 403 and

404 of the Federal Rules of Evidence—Kaminski is

bad law. See Marcus, supra, § 4.05I (Stressing the

need, post-Jacobson, “to distinguish between prior

acts, as opposed to prior crimes. The former involves

far more dangerous [predisposition] possibilities than

the latter”) (emphasis original). Indeed, the Fourth

Circuit’s decision to follow Kaminski over Jacobson

creates a set piece of the injustices posed by a bluntly

defined “subjective” entrapment test of which various

Justices have presciently warned over the years.

The subjective entrapment test, also known as the

Sherman-Sorrells test, focuses on the defendant’s psychological state—his thoughts—before being induced

to commit the crime. Sherman, 356 U.S. at 376; Sorrells v. United States, 287 U.S. 435 (1932). Both decisions drew sharp concurrences that homed in on the

subjective test’s drawbacks. In Sorrells, Justice Roberts, joined by Justices Brandeis and Stone, faulted

the subjective test for “pivot[ing] conviction [] not on

the commission of the crime charged, but on the prior

reputation or some former act of the defendant not

18

mentioned in the indictment.” 287 U.S. at 458-59 (emphasis added). Building on Justice Roberts’ concurrence, Justice Frankfurter, concurring in Sherman

and joined by Justices Douglas, Harlan and Brennan,

added that, contra the subjective test, “no matter

what the defendant’s past record and present inclinations to criminality, or the depths to which he has sunk

in the estimation of society, certain police conduct to

ensnare him into further crime is not to be tolerated

by an advanced society.” 356 U.S. at 383 (emphasis

added); see also Russell, 411 U.S. at 440 (Justice Stewart objecting in dissent that the subjective test threatens “the introduction into evidence of all kinds of

hearsay, suspicion and rumor—all of which would be

inadmissible in any other context”).

Justices Roberts and Frankfurter were making

the case for an objective entrapment test—one exclusively asking whether the government “employed

methods of persuasion or inducement which create a

substantial risk that such an offense will be committed by persons other than those who are ready to commit it” and considering “surrounding circumstances

such as evidence of the manner in which the particular criminal business is unusually carried on.”

LaFave, Israel, King, Kerr, Criminal Procedure §

5.2(a) (4th ed. 2015). Although some courts of appeals

hold that objectivity plays no current role in entrapment law (see infra), the objective test is favored by a

majority of criminal law commentators and has been

adopted by the American Law Institute’s Model Penal

Code (ALI Model Penal Code § 2.13) and by one-third

of the states either by statute or judicial decision. Id.

at § 5.2(b).

19

The current circuit split notwithstanding, one

prominent criminal law commentator has observed

that “it is important to recognize that [an] indiscriminate attitude toward predisposition evidence is by no

means a necessary feature of the subjective test.”

LaFave, Israel, King, Kerr, supra, at § 5.2(b). To take

the example ready to hand, the Court can clarify here

that Jacobson limited predisposition proof to evidence

that the defendant has previously been convicted of

the charged crime or a “similar” one, or evidence the

defendant previously committed—or planned, attempted or conspired to commit—the same or similar

crime but was not charged. 503 U.S. at 551 (“evidence

of predisposition to do what once was lawful is not, by

itself, sufficient to show predisposition to do what is

now illegal.”).

In material-support cases such as this one, the balance between the accused’s First Amendment rights

and the government’s predisposition burden would

pivot on Brandenburg. If the proposed predisposition

evidence amounted to the announcement of a concrete

plan, boasting of past terrorism-related offenses, or

incitement to imminent terrorism, it is admissible under Jacobson-Brandenburg. Mere statements of sympathy or political advocacy would not be. Brandenburg, 395 U.S. at 447; see also Sherman, “A Person

Otherwise Innocent”: Policing Entrapment in Preventative, Undercover Counterterrorism Investigations,

11 U. PA. J. CONST. L. 1475, 1506 (2009) (advocating

Brandenburg predisposition test).

Such clarification would correctly identify the district court’s grievous twofold error here: converting a

20

militant Islamist terrorism trial into a hate crime

trial where no hate crime was ever so much as investigated; and effectively convicting a man for the exercise of his First Amendment rights. Left alone, the

precedent is set for politically motivated sting operations lurking behind the fig leaf of token pretextual

crime.

II. THE COURTS OF APPEALS ARE DIVIDED

OVER WHETHER THE PREDISPOSITION

ELEMENT CONTAINS AN OBJECTIVE

“POSITIONAL” COMPONENT BEYOND

THE SUBJECTIVE “DISPOSITIONAL” ONE

A. The Seventh, First and Fifth Circuits Require Proof the Defendant Was Objectively Positioned to Commit the Crime Absent Government Intervention

Part of Jacobson’s analysis is not found in the

Court’s previous entrapment decisions. Entrapment,

Jacobson uniquely held, is “the apprehension of an

otherwise law-abiding citizen who, if left to his own

devices, likely would have never run afoul of the law.”

503 U.S. at 553-54. That citizen was Jacobson. Yet

Jacobson did have a psychological predisposition to

consume child pornography (albeit one that was

demonstrated with then legally acquired magazines).

Only, as a farmer in Nebraska, his ability to obtain

child pornography in the pre-internet age was nonexistent. Duly, over the course of the two-year investigation, agents did not witness Jacobson receiving any

non-governmental solicitations to buy pornography.

503 U.S. at 545. It was not Jacobson’s mental state

alone—or at all—that allowed the Court to conclude

21

that had he been “left to his own devices,” in all likelihood he would “have never run afoul of the law.” Id.

at 553-54. It was the totality of the circumstances—

subjective and objective.

This reading of Jacobson neatly harmonizes with

the Court’s foundational precedent in another area of

criminal law—probable cause. Entrapment and probable cause analyses are illuminatingly analogous. In

both situations, the court understands in hindsight a

crime has been committed. The court then temporally

places itself in law enforcement’s mindset before the

crime was committed (entrapment) or uncovered

(probable cause) and asks whether it was probable

that a crime would be committed or found. In Illinois

v. Gates, for example, the Court held that, in such a

“fluid” context, “turning on the assessment of probabilities in particular factual contexts,” common sense

dictates that “[r]igid legal rules are ill-suited to an

area of such diversity [probable cause determinations].” 462 U.S. 213, 232 (1983). An objective, totality-of-the-circumstances test was applied. Id. Just as

the rigid pre-Gates probable cause formulae did not

adequately capture the true probability of uncovering

evidence of crime, a rigidly psychological entrapment

test fails to measure the probability of a future crime’s

commission. See, e.g., Zalaski v. City of Hartford, 723

F.3d 382, 393-94 (2d Cir. 2013) (probable cause determination blends assessment of defendant’s subjective

intent with objective surrounding circumstances).

The Seventh Circuit has adopted this interpretation of Jacobson. See United States v. Hollingsworth,

27 F.3d 1196 (7th Cir. 1994) (en banc) (Posner, C.J.).

22

There, a dentist tried his hand at international finance, opening a Virgin Islands bank and advertising

for customers. While attending a money laundering

seminar, a customs agent spotted the dentist’s ad. Assuming a pseudonym, the agent began pitching

money laundering schemes to the dentist. For over

half a year, the agent could not get the dentist to express agreement. Ultimately, nearly a year after they

first communicated, the agent persuaded the dentist

to launder $200,000 in proceeds from “the smuggling

of guns to [then apartheid] South Africa.” Arrested,

the dentist was carrying a fake-name passport issued

by the mythical “Dominion of Melchizedek,” acquired

after meeting the agent. 27 F.3d at 1200-03.

Applying Jacobson, Chief Judge Posner elucidated

why “left to his own devices,” in all likelihood the dentist never would “have never run afoul of the law.” Id.

at 1202. Before the agent began his sting, there was

no evidence the dentist had ever considered money

laundering or ever engaged in any financial wrongdoing. The dentist’s bank was on the verge of closing.

The bank had never attracted a single customer other

than the agent, who was the only person to ever respond to the ad. The dentist was in slow decline: “Had

[the agent] not answered the ad, [the dentist] would

have soon folded his financial venture. It would have

joined his other failures—his movie theaters that

failed, his amusement park that failed, his apartment

building that failed, his attempt to market cookbooks

written by his wife that failed.” Id. at 1202.

The point was not that the dentist was psychologically “incapable of engaging in the act of money laundering. . . . But to get into the international money-

23

laundering business you need underworld contacts, financial acumen or assets, access to foreign banks or

bankers, or other assets. [The dentist] had none.

Even if [he] wanted to go into money laundering before [he] met [the agent], the likelihood that [he] could

have done so was remote. [Like Jacobson, he] was objectively harmless.” 27 F.3d at 1202 (emphasis original); see also United States v. Mayfield, 771 F.3d 417,

428 (7th Cir. 2014) (“[P]redisposition is largely probabilistic, not psychological.”)

Decisions in the Fifth and First Circuits are in accord. See United States v. Reyes, 239 F.3d 722, 739

(5th Cir. 2001) (applying Hollingsworth); United

States v. Wise, 221 F.3d 140, 155-56 (5th Cir. 2000)

(same); Untied States v. Gamache, 156 F.3d 1, 11-12

(1st Cir. 1998) (citing Hollingsworth and holding that

the defendant’s “stated willingness to commit the

crime, although clearly relevant to the jury’s inquiry,

is not sufficient by itself to mandate a finding that he

was predisposed”); United States v. Gendron, 18 F.3d

955, 963 (1st Cir. 1993) (Breyer, C.J.) (Following Jacobson, a defendant is not entrapped if “[h]e is [] someone who would likely commit the crime under the circumstances and for the reasons normally associated

with that crime….”) (emphasis added).

B. The Second and Ninth Circuits, and the

District Court Here, Have Strayed from

Jacobson

The Second and Ninth Circuits have rejected Hollingsworth’s interpretation of Jacobson. See Cromitie,

727 F.3d at 216-17; United States v. Thickstun, 110 F.

3d 1394, 1398 (9th Cir. 1997). Rather, both decisions

reject caricatures of the Hollingsworth rule.

24

In Thickstun, a bribery case, the Ninth Circuit reasoned that Hollingsworth’s interpretation of Jacobson

must be misplaced, as it was unnecessary for the Jacobson court to transcend ordinary subjective analysis

given the “absence of evidence of predisposition.” 110

F.3d at 1398. Yet, as shown above, there was evidence of Jacobson’s pre-investigation interest in child

pornography. Jacobson, 503 U.S. at 542. Thickstun

also reasoned that Jacobson-Hollingsworth “would be

especially problematic in bribery cases [since] a person is never ‘positionally’ able to bribe a public official

without cooperation from that official.” 110 F.3d at

1398. That is a crabbed understanding of JacobsonHollingsworth. In a bribery case, Jacobson-Hollingsworth does not turn a blind eye to every circumstance beyond the briber’s personal “position.” Instead, it inquires whether, for example, apart from

the sting operation, the briber enjoyed contacts with

real world officials, whether he had ever attempted to

make contacts, whether those officials were venal,

whether the briber had ever attempted to bribe them,

and whether he had a motive to do so.

In Cromitie, a material-support-for-terrorism entrapment case, the panel’s majority rejected an objective “positional” predisposition analysis with one sentence: “A person who has a pre-existing design to commit terrorist acts against United States interests, or

who promptly agrees to play a part in such activity,

should not escape punishment just because he was

not in a position to obtain Stinger missiles and launch

them at United States airplanes.” 727 F.3d at 216.

What this abbreviated analysis neglects to consider are the primary statutes with which terrorism

25

defendants are charged—18 U.S.C. §§ 2339A and

2339B—which do not merely cover such support as

the provision of Stinger missiles. See, e.g., Trial and

Terror, The Intercept_(Mar. 7, 2019), http://trial-andterror.theintercept.com (51% of terrorism defendants

charged with §§ 2339A and 2339B). Indeed, “Material

support or resources” in those statutes means:

any property, tangible or intangible, or service, including currency or monetary instruments or financial securities, financial services, lodging,

training, expert advice or assistance, safehouses,

false documentation or identification, communications equipment, facilities, weapons, lethal substances, explosives, personnel (1 or more individuals who may be or include oneself), and transportation, except medicine or religious materials.

18 U.S.C. § 2339A(b)(1).

There is no de minimis exception to “material support or resources” and the government need not prove

the defendant provided the support or resources with

the specific intent to further the FTO’s illegal activities; it must only show the defendant knew the recipient of the support or resources was affiliated with a

group connected to terrorism. See, e.g., Rayamajhi v.

Whitaker, 912 F.3d 1241, 1245 (9th Cir. 2019) (“[T]he

material support bar does not contain an exception for

people who merely give de minimis funds to a terrorist organization.”); Holder v. Humanitarian Law Project, 561 U.S. 1, 130 (2010) (specific intent to advance

the FTO’s terrorist activities is not essential).

26

With the full sweep of the material-support statutes in view, the danger of rejecting Jacobson-Hollingsworth’s objective positional test in terrorism

sting operations becomes no less clear than the absence of true risk in its proper application. Consider

the following hypothetical material-support investigations.

In the first, assume A falsely believes that his

friend, undercover informant B, has associated himself with an FTO. Over dinner at a fine restaurant, A

admonishes B to discontinue immediately his relationship with the terror group. B demurs. Following

the meal, B confesses he has forgotten his wallet—

would A mind paying the $245 bill this time? (B had

insisted on ordering expensive arak.) Although initially disinclined, A is at length prevailed upon to foot

the bill. Since money is fungible—and specific intent

to further the FTO’s illegal activities is not required—

A is now guilty of attempting to provide material support to an FTO, unless he was entrapped. The Jacobson-Hollingsworth test does not eschew an analysis of

A’s mental disposition prior to meeting B. It simply

adds such commonsense questions as: in the real

world, does this FTO acquire resources in this manner

from Americans? Is it likely to? If not, can it be fairly

inferred from a person’s willingness to split a dinner

bill that he would be willing to send money overseas,

willing to harm the innocent? Have any of the FTO’s

members ever communicated with A? Has he tried to

communicate with them? Are they likely to in the future?

27

In the second case, again assume A falsely believes

that his friend, undercover informant B, has associated himself with an FTO. This time, however, B tells

A the FTO is searching for a secret weapon called Melchizedek. In reality, Melchizedek either does not exist or is virtually impossible to secure, but B leads A

to believe it does. B asks A to provide $245 to acquire

one component of Melchizedek. A obliges. Here, it is

true, the Jacobson-Hollingsworth test would indeed

ask whether, absent government intervention, A

would likely have given resources to the FTO for the

acquisition of nonexistent Melchizedek. But Jacobson-Hollingsworth’s

totality-of-the-circumstances

test would not stop there. It would also ask: what did

A “know” about the purpose of the weapon? Is that

purpose analogous to one pursued by the FTO in the

real world? Does the FTO seek resources from Americans to acquire its real weapons? Even if not, as an

empirical matter is a demonstrated willingness to

send money to an FTO indicative of a disposition to

commit a “lone-wolf” act of terrorism, which demonstrably exists in the real world?

Properly applied, then, Jacobson-Hollingsworth

does not create the “Stinger missile problem” identified by the Cromitie majority. 727 F.3d at 216. It does,

however, prevent cases—like this one—which flout

Jacobson’s rule that entrapment is “the apprehension

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

own devices, likely would have never run afoul of the

law.” 503 U.S. at 553-54. Or, more precisely, it arms

fact-finders with a discretionary veto over liberty/security balancing which would otherwise be struck by

28

security services sub rosa, without public accountability. Here, the district court denied Petitioner’s motion

for acquittal before submission of the case to the jury

even though the government offered no evidence that:

(1) the FTO seeks Google Play gift cards, or other

small financial contributions, from Americans; (2) Petitioner ever communicated with, or attempted to

communicate with, the FTO in the real world; (3) the

FTO was likely to request a contribution from Petitioner; or (4) Petitioner’s willingness to send gift cards

foreshadowed an inclination to contribute to activities

actually practiced by an FTO. App. 39a.

Petitioner’s case is not sui generis. Starting with

the most specific comparison, this particular gift-card

operation has been repeatedly used by the FBI—

though without evidence presented that it reflects the

real-world activity of the relevant FTO. See, e.g.,

United States v. Lionel Williams, 17-CR-01, Dkt. 47

(E.D. Va. Dec. 20, 2017) (sentencing defendant to

twenty years’ incarceration for sending $50 to an undercover agent he believed was associated with an

FTO); United States v. Harris Qamar, 16-CR-227,

Dkt. 43 (E.D. Va. Feb. 17, 2017) (sentencing defendant to eight years’ incarceration for sending $40 in

Google Play gift cards to a person he believed was associated with an FTO).

Myriad similar cases appear to involve defendants

lacking demonstrated connections to real-world terror

groups prior to sting operations. See, e.g., United

States v. Bouterse, 13-CR-635 (S.D.N.Y. Mar. 3, 2015)

(sentencing son of president of Suriname to 16 years’

incarceration for inter alia agreeing to informant’s

scheme to send “Hezbollah trainees” to Caribbean

29

country with no known connections to international

terrorism); United States v. Rahatul Kahn, 14-CR212, Dkt. 53 (W.D. Tex. Sept. 29, 2015) (sentencing

defendant to ten years’ incarceration for conversations with informant about the latter’s feigned interest in joining FTO); United States v. Oumar Issa, et

al., 09-CR-1244 (S.D.N.Y. Mar. 12, 2012 ) (sentencing

defendants from poor African village to five years’ incarceration for agreeing with an informant, posing as

a “Colombian narco-gang member,” to “transport cocaine” from West Africa to Spain “on behalf of al

Qaeda”). See generally Trial and Terror, The Intercept (Mar. 7, 2019), http://trial-and-terror.theintercept.com.

Since it ameliorates some of the strongest criticisms of a subjective entrapment test, many legal

commentators have supported Hollingsworth’s interpretation of Jacobson. LaFave, Israel, King, Kerr, supra, § 5.2(b); see also McAdams, Reforming Entrapment Doctrine in United States v. Hollingsworth, 74

U.Chi.L.Rev.1795 (2007).

This case presents an opportunity for the Court to

resolve the circuit split over Hollingsworth and

thereby improve on the subjective entrapment test.

When the government secures a man’s conviction of a

crime it induced him to commit—and which he may

have been mentally disposed to commit—but which

he likely would not have committed in his objective

circumstances absent government intervention, it is

punishing thoughtcrime. That is Petitioner’s case.

30

CONCLUSION

For the foregoing reasons, the petition for a writ of

certiorari should be granted.

Respectfully submitted,

David B. Smith

Counsel of Record

Nicholas David Smith

DAVID B. SMITH PLLC

7 East 20th Street, Suite 4R

New York, NY 10003

(917) 722-1096

nds@davidbsmithpllc.com

dbs@davidbsmithpllc.com

Counsel for Petitioner

May 16, 2019