United States v. Farooq

21-0707
United States v. Farooq
United States Court of Appeals
for the Second Circuit
August Term 2022
Argued: November 23, 2022
Decided: January 30, 2023
No. 21-0707
U NITED S TATES OF AMERICA,
Appellee,
v.
K HAWAJA MUHAMMAD F AROOQ ,
Defendant-Appellant.
On Appeal from the United States District Court
for the Eastern District of New York
Before: K EARSE , PARK, and MENASHI, Circuit Judges.
Defendant-Appellant Khawaja Muhammad Farooq pled guilty
to one count of extortion under 18 U.S.C. § 875(d) for threatening to
disseminate nude photographs of Jane Doe if she did not return to a
relationship with him. Farooq now appeals, arguing that the plea
proceedings were defective because the district court did not explain
the “wrongfulness” element of extortion under United States v.
Jackson, 180 F.3d 55 (2d Cir. 1999). He also challenges two special

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conditions of supervised release on First Amendment grounds: (1) a
requirement that Farooq seek retraction of articles he published about
Jane Doe and her brother-in-law, John Doe, and (2) a requirement that
he seek approval from the district court before publishing any further
information about them.
We conclude as follows: First, the plea proceedings were not
defective because the district court correctly determined that Farooq
understood the “nature of each charge” to which he pled. Fed. R.
Crim. P. 11(b)(1)(G). Jackson does not require a separate explanation
of “wrongfulness” under 18 U.S.C. § 875(d) when, as here, the
defendant stipulates that he has no plausible claim of right to the
thing of value. See 180 F.3d at 70–71. Second, the special condition
that Farooq seek retraction of articles he published about Jane Doe
and John Doe has expired, so Farooq’s challenge to that condition is
moot. Finally, the special condition that Farooq seek approval from
the district court before publishing further information about Jane
Doe and John Doe does not violate the First Amendment under the
circumstances here. Farooq pled guilty to extortion by threatening
to publish nude images of Jane Doe, and he is a journalist who had
published or threatened to publish information about her and John
Doe in the past. So the district court acted within its broad discretion
by imposing the narrowly tailored special condition requiring Farooq
to obtain approval from the court before publishing any further
information about them. We thus AFFIRM.
JOSHUA PHILIP B USSEN (Brian A. Jacobs, on the brief),
Morvillo Abramowitz Grand Iason & Anello P.C., New
York, NY, for Defendant-Appellant.
K AYLA C. B ENSING (Amy Busa, on the brief), Assistant
United States Attorneys, for Breon Peace, United States
Attorney for the Eastern District of New York, New York,
NY, for Appellee.

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PARK, Circuit Judge:
Defendant-Appellant Khawaja Muhammad Farooq pled guilty
to one count of extortion under 18 U.S.C. § 875(d) for threatening to
disseminate nude photographs of Jane Doe if she did not return to a
relationship with him. Farooq now appeals, arguing that the plea
proceedings were defective because the district court did not explain
the “wrongfulness” element of extortion under United States v.
Jackson, 180 F.3d 55 (2d Cir. 1999). He also challenges two special
conditions of supervised release on First Amendment grounds: (1) a
requirement that Farooq seek retraction of articles he published about
Jane Doe and her brother-in-law, John Doe, and (2) a requirement that
he seek approval from the district court before publishing any further
information about them.
We conclude as follows: First, the plea proceedings were not
defective because the district court correctly determined that Farooq
understood the “nature of each charge” to which he pled. Fed. R.
Crim. P. 11(b)(1)(G). Jackson does not require a separate explanation
of “wrongfulness” under 18 U.S.C. § 875(d) when, as here, the
defendant stipulates that he has no plausible claim of right to the
thing of value. See 180 F.3d at 70–71. Second, the special condition
that Farooq seek retraction of articles he published about Jane Doe
and John Doe has expired, so Farooq’s challenge to that condition is
moot. Finally, the special condition that Farooq seek approval from
the district court before publishing further information about Jane
Doe and John Doe does not violate the First Amendment under the
circumstances here. Farooq pled guilty to extortion by threatening
to publish nude images of Jane Doe, and he is a journalist who had
published or threatened to publish information about her and John

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Doe in the past. So the district court acted within its broad discretion
by imposing the narrowly tailored special condition requiring Farooq
to obtain approval from the court before publishing any further
information about them. We thus affirm.
I. BACKGROUND
A. Facts1
Farooq met Jane Doe in 2013 when she traveled from Pakistan
to the United States for business. They remained in touch and began
a romantic relationship after she returned to Pakistan. They
communicated over Skype and WhatsApp and had some accounts
with shared passwords. In 2016, Farooq asked Jane Doe’s family for
permission to marry her, and the family refused. Jane Doe ended
the relationship shortly after that. Farooq continued to contact Jane
Doe, but she did not respond.
Farooq then began sending emails and text messages to Jane
Doe’s coworkers. He also sent individuals to Jane Doe’s workplace
to ask her to contact him. In early 2018, one of Jane Doe’s coworkers
told her that Farooq was asking Jane Doe to log on to a shared Skype
account to see some photos. She logged on and saw sexually explicit
photos that Farooq had taken of her without her consent. Farooq
threatened to share the photos with her family, coworkers, and village
if she did not call him. Farooq knew that Jane Doe is from a
conservative village in Pakistan where women may be harmed or
even killed if they are perceived to bring dishonor on their families.
1 Unless otherwise noted, all facts are drawn from the Presentence
Investigation Report (“PSR”), which the district court adopted in its entirety
at sentencing.

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Farooq’s threatened disclosure of the photos thus caused Jane Doe
substantial distress and fear.
Jane Doe shared what was happening with her brother-in-law
John Doe. Farooq continued to send threatening messages to Jane
Doe: “Don’t treat anyone like a dog. When a dog becomes crazy, it
bites and its poisonous bite can kill a person. . . . You treated me less
than a dog. . . . You would not have listened to me, if I had not saved
all your pictures.” PSR ¶ 10. He also sent threatening messages to
John Doe, stating that he would send the photos to John Doe’s
colleagues, get him fired, and “destroy” him. Id. ¶ 18.
At the time, Farooq worked as a journalist for a Pakistani
publication and carried a United Nations press pass. He referenced
his press access in his messages to Jane Doe and John Doe, including,
for example, by stating to John Doe: “I have started the proceedings
with a local TV channel in the US. I am requesting you to stop this
non sense [sic] . . . otherwise this news will broadcast on CNN, Fox
news and BBC London.” District Ct. Doc. No. 59, Ex. 3. Farooq
messaged one of Jane Doe’s coworkers that “it’s better for [Jane Doe]
to talk to me. Otherwise I will post her nude pictures and whatever
[John Doe] is saying about her, on all the university websites and
social media.” PSR ¶ 15. Farooq also contacted the Prime Minister
of Pakistan, the Chief Justice of the Pakistani Supreme Court, the
Consul General of Pakistan to the United States in New York, and the
Chief Minister of Punjab with information about Jane Doe and John
Doe.
Farooq’s messages came to the attention of the FBI, and he was
arrested in Brooklyn in 2019.

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B. Procedural History
The government charged Farooq with two counts of extortion
with threats to injure Jane Doe and John Doe under 18 U.S.C. § 875(c)
and two counts of extortion with threats to injure their reputations
under 18 U.S.C. § 875(d).
1. The Plea Proceeding
In June 2019, Farooq pled guilty to Count Two of the
indictment—extortion of Jane Doe under 18 U.S.C. § 875(d). At the
plea hearing, he admitted the following: “On September 16, 2018, I
sent an e-mail from Brooklyn, New York to a woman in Pakistan
called Jane Doe in the indictment and I threatened to send naked
pictures of her to other men in Pakistan unless she came back to me.”
App’x at 208. During the plea colloquy, Farooq’s counsel had the
following exchange with the district court:
Defense counsel: Your Honor, if I may add as a matter
of law, there are two elements that I think are legal
questions rather than factual. I’ve discussed with Mr.
Farooq, and he will stipulate, that the relationship that he
sought to have with Jane Doe, if she complied with his
requests, is a quote, “thing of value.”
The Court: That’s what I was going to ask you.
Defense counsel: And is also not something to which
he was legally entitled.
The Court: So you would stipulate to the fact that this
relationship meets the definition of thing of value for
purposes of Section 875(d)?

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Defense counsel: I would. And that his threat to send
the pictures in exchange for that thing of value
constitutes legal extortion.
Id. at 208–09. Farooq also stipulated that his “intention” was to make
Jane Doe “feel that if she did not come back to [him, Farooq] would
send the pictures to other men.” Id. at 210.
Seven months later, Farooq, proceeding pro se, moved to
withdraw his guilty plea, arguing that it was not voluntary and that
the statements he made during the plea proceeding were false and
coerced by his attorney. The district court denied Farooq’s motion
to withdraw the guilty plea because of the delay between his plea and
the motion, the failure to raise any new evidence to support his claims
of innocence, and the absence of evidence of coercion. See United
States v. Farooq, No. 19-CR-100, 2020 WL 1083624, at *2–6 (E.D.N.Y.
Mar. 6, 2020).
The district court also denied Farooq’s subsequent motions to
withdraw his guilty plea after reviewing transcripts that Farooq
argued would show his innocence. The court concluded that the
transcripts did not support his new theory that Jane Doe consented to
the extortion to persuade John Doe to let her return to her relationship
with Farooq.
2. Sentencing
The district court sentenced Farooq to the maximum sentence
of two years’ imprisonment with one year of supervised release.
The district court imposed two special conditions of supervised
release at issue on appeal:
[1] The defendant shall endeavor to have retracted any
newspaper or press article that he has facilitated the

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publishing or posting of, either directly or indirectly, and
that contains the true name or other personal identifying
information, place of employment, or visual image of
John Doe or Jane Doe.
[2] The defendant shall refrain from disseminating any
information about Jane Doe or John Doe in any medium,
either directly or indirectly, including through other
individuals, absent seeking and obtaining permission
from the Court.
District Ct. Doc. No. 142 at 5.
3. Post-Sentencing Developments
Farooq’s initial term of supervised release was set to expire in
April 2022. In March 2022, the district court extended that initial
term to resolve Farooq’s alleged violation of the conditions of his
supervised release. Farooq pled guilty to one count of violating the
conditions of supervised release by contacting John Doe. In
November 2022, the district court sentenced Farooq to time served
and imposed a renewed term of supervised release set to expire on
February 9, 2023. The new term of supervised release included the
special condition prohibiting dissemination of information about Jane
Doe and John Doe, but it did not renew the condition requiring
Farooq to seek retraction of articles he published about Jane Doe and
John Doe.
II. DISCUSSION
Farooq argues that the district court erred by not separately
explaining the “wrongfulness” element of extortion to him during the
plea proceeding. This argument is without merit. Federal Rule of
Criminal Procedure 11 requires that the defendant understand the

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“nature of each charge” against him. Farooq’s stipulations during
the plea proceeding confirm that he understood the nature of the
extortion charge under 18 U.S.C . § 875(d), including its
“wrongfulness.”
Farooq further challenges the special conditions of supervised
release on First Amendment grounds. First, the special condition
requiring Farooq to seek retraction of articles he published is now
moot. Second, the special condition requiring the district court’s
approval before Farooq publishes information about Jane Doe and
John Doe is narrowly tailored under the circumstances here.
A. The Plea Proceeding
1. Legal Standards
We review Farooq’s challenge to the plea proceeding for plain
error because he did not object below. United States v. Balde, 943 F.3d
73, 95 (2d Cir. 2019). To show plain error, there must (1) be an error
that (2) is “clear or obvious, rather than subject to reasonable
dispute,” and (3) the error must have “affected the appellant’s
substantial rights,” and (4) have “seriously affect[ed] the fairness,
integrity or public reputation of judicial proceedings.” Id. at 96
(citation omitted).
Rule 11 of the Federal Rules of Criminal Procedure requires
that the district court “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). Rule 11 does
not require that the judge personally “explain the elements of each
charge to the defendant on the record” as long as “the record
accurately reflects that the nature of the charge and the elements of

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the crime were explained to the defendant by his own, competent
counsel.” Bradshaw v. Stumpf, 545 U.S. 175, 183 (2005); see also United
States v. Torrellas, 455 F.3d 96, 102 (2d Cir. 2006) (“[W]hile Rule 11
imposes strict requirements on what information the district courts
must convey and determine before they accept a plea, it does not tell
them precisely how to perform this important task in the great variety
of cases that come before them.” (cleaned up)).
Farooq pled guilty to extortion under 18 U.S.C. § 875(d), which
states: “Whoever, with intent to extort from any person . . . any
money or other thing of value, transmits in interstate or foreign
commerce any communication containing any threat to injure the
property or reputation of the addressee . . . shall be fined under this
title or imprisoned not more than two years, or both.” The statute
does not include the word “wrongfulness,” but we have clarified that
§ 875(d) contains an implicit wrongfulness element. United States v.
Jackson, 180 F.3d 55, 70 (2d Cir. 1999).
2. Application
The question here is whether Farooq understood the “nature of
[the extortion] charge.” Fed R. Crim. P. 11(b)(1)(G). Farooq argues
that it was plain error here for the district court not to explain on the
record the wrongfulness element as articulated by Jackson. But
neither the extortion statute nor Jackson supports his argument.
As an initial matter, Jackson involved jury instructions, which
are generally held to a higher standard than the district court’s
guidance during a plea proceeding. See United States v. Saft, 558 F.2d
1073, 1079 (2d Cir. 1977) (“The contention that even in [a plea
proceeding] the judge must deliver to the defendant the equivalent of

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a jury charge finds no support in the language of [Rule 11] and runs
counter to the legislative history.”).
In any event, Farooq misreads Jackson’s analysis of
“wrongfulness.” The defendant in that case requested a jury
instruction separately explaining the “wrongfulness” element of
extortion. Jackson, 180 F.3d at 65. The district court rejected the
proposed jury instruction because “threatening someone’s reputation
for money or a thing of value is inherently wrongful.” Id. (citation
omitted). We clarified, however, that a threat to reputation is not
wrongful under § 875(d) if the person has a plausible claim of right to
the thing of value. Id. at 67 (“For example, the purchaser of an
allegedly defective product may threaten to complain to a consumer
protection agency or to bring suit in a public forum if the
manufacturer does not make good on its warranty.”). So the jury
instructions would have been proper if they made clear that the
“threat to disclose was issued in connection with a claim for [a thing
of value] to which she was not entitled or which had no nexus to a
plausible claim of right.” Id. at 71.
The record reflects that Farooq understood the wrongfulness of
his conduct. He stipulated that the relationship he sought to have
with Jane Doe is a “thing of value” and is “not something to which he
was legally entitled.” App’x at 209. Under Jackson, that amounted
to an admission that Farooq’s threat was “inherently wrongful.” 180
F.3d at 71. And the threat to Jane Doe’s reputation—i.e., the
dissemination of nude pictures—“had no nexus with any plausible
claim of right.” Id. at 70 (noting that threats of disclosure of “sexual
indiscretions” are “inherently wrongful”). Thus, Farooq’s
stipulation makes clear that he understood the nature of the charge

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against him, including the inherent wrongfulness of his conduct.
We conclude that there was no plain error in his plea allocution.2
B. The Conditions of Supervised Release
1. Legal Standards
We review special conditions of supervised release for abuse of
discretion. United States v. McLaurin, 731 F.3d 258, 261 (2d Cir. 2013).
But “[w]hen a challenge to a condition of supervised release presents
an issue of law, we review the imposition of that condition de novo,
bearing in mind that any error of law necessarily constitutes an abuse
of discretion.” Id. (citation omitted).
In general, “a district court may impose special conditions of
supervised release that are reasonably related to certain statutory
factors governing sentencing, involve no greater deprivation of
liberty than is reasonably necessary to implement the statutory
purposes of sentencing, and are consistent with pertinent Sentencing
Commission policy statements.” United States v. Eaglin, 913 F.3d 88,
94 (2d Cir. 2019) (cleaned up). Relevant factors include the “nature
and circumstances of the offense,” “the history and characteristics of
the defendant,” and the need for “adequate deterrence,” “protect[ing]
the public from further crimes,” and “provid[ing] the defendant with
needed . . . correctional treatment in the most effective manner.”
United States v. Bolin, 976 F.3d 202, 210 (2d Cir. 2020) (quoting U.S.S.G.
2 For the same reasons, the district court acted within its broad
discretion to deny Farooq’s motion to withdraw his guilty plea. The
district court determined that Farooq’s “statement that everything [he] said
during that plea proceeding was a lie” was not “credible” and that there
was no “support in the record that [his] lawyer improperly pressured [him]
into pleading guilty.” App’x at 399.

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§ 5D1.3(b)(1)). For fundamental liberty interests, the condition is
“’reasonably necessary’ only if the deprivation is narrowly tailored to
serve a compelling government interest.” Id. (quoting United States
v. Myers, 426 F.3d 117, 126 (2d Cir. 2005)).
2. Retraction Requirement
The special condition of supervised release requiring Farooq to
seek retraction of articles he published about Jane Doe and John Doe
has expired, so his challenge to this condition is moot. In November
2022, the district court did not renew this condition when sentencing
Farooq for the violation of his initial term of supervised release.
Farooq asserts that his challenge to the condition is not moot because
it is “capable of repetition, yet evading review.” Turner v. Rogers, 564
U.S. 431, 440 (2011). We are unpersuaded.
Expiration or modification of a special condition of supervised
release typically moots an appeal challenging that condition. See
United States v. Juv. Male, 564 U.S. 932, 936 (2011) (holding that there
is no presumption of collateral consequences for an expired sentence);
United States v. Johnson, 446 F.3d 272, 276 (2d Cir. 2006) (noting that an
objection to a condition of supervised release became moot when the
condition was modified). The district court did not renew this
condition, and there is no indication that it would reimpose it again.3
Farooq’s appeal of this condition is thus moot.
3 Farooq’s reliance on United States v. Melton, 666 F.3d 513 (8th Cir.
2012), is misguided. That case involved different circumstances in which
the defendant had been ordered multiple times to complete stays at a
halfway house for time periods that were too short to challenge in court
before they ended. See id. at 515 n.3.

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3. Publishing Limitation
Farooq also challenges the special condition of supervised
release requiring him to seek the district court’s approval before
disseminating any information about Jane Doe and John Doe.
Although this condition restricts Farooq’s First Amendment rights,
we conclude that it was within the district court’s discretion to impose
this condition under the circumstances here. The condition is closely
related to Farooq’s criminal conduct and is narrowly tailored to
protect Jane Doe and John Doe in light of Farooq’s history of
threatening them and his background as a journalist.
As a general matter, conditions that would be unconstitutional
“when cast as a broadly-applicable criminal prohibition” may be
“permissible when imposed on an individual as a condition of
supervised release.” Eaglin, 913 F.3d at 96. The constitutional
rights of defendants subject to conditions of supervised release may
be limited. See, e.g., Farrell v. Burke, 449 F.3d 470, 497 (2d Cir. 2006)
(“[W]e note that the First Amendment rights of parolees are
circumscribed.”); Porth v. Templar, 453 F.2d 330, 334 (10th Cir. 1971)
(“[One on probation] forfeits much of his freedom of action and even
freedom of expression to the extent necessary to successful
rehabilitation and protection of the public programs.”).
We recognize that the special condition of supervised release
prohibiting Farooq from “disseminating any information about Jane
Doe or John Doe in any medium . . . absent seeking and obtaining
permission from the Court” is a content-based prior restraint on
speech. See United States v. Quattrone, 402 F.3d 304, 309 (2d Cir. 2005)
(defining a prior restraint as a “judicial order that suppresses
speech—or provides for its suppression at the discretion of

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government officials—on the basis of the speech’s content and in
advance of its actual expression”). And there is “a heavy
presumption against [the] constitutional validity” of “[a]ny
imposition of a prior restraint.” Id. at 310 (quoting Bantam Books, Inc.
v. Sullivan, 372 U.S. 58, 70 (1963)). We have thus vacated overly
broad conditions of supervised release implicating First Amendment
rights. See, e.g., Bolin, 976 F.3d at 215–16 (vacating as
unconstitutional condition of supervised release prohibiting
defendant from engaging in internet speech “that promotes or
endorses violence, unlawful activity, or any groups that espouse such
ideas”). But see, e.g., United States v. Schiff, 876 F.2d 272, 276–77 (2d
Cir. 1989) (upholding as constitutional condition prohibiting
association with groups advocating noncompliance with tax laws).
Under the circumstances of this case, the special condition is
narrowly tailored. First, it is “reasonably related” to the “nature and
circumstances” of Farooq’s offense. U.S.S.G. § 5D1.3(b)(1). The
charged conduct and the conduct to which Farooq pled guilty related
to exposing Jane Doe’s and John Doe’s identities and disseminating
information that would embarrass and harm them. Farooq pled
guilty to emailing Jane Doe and “threaten[ing] to send naked pictures
of her to other men in Pakistan unless she came back to [him].”
App’x at 208. Farooq also contacted Jane Doe and John Doe both
directly and indirectly through their coworkers. So the conduct
covered by the special condition is closely related to the conduct for
which Farooq was charged.
Second, the special condition is closely related to Farooq’s
“history and characteristics.” U.S.S.G. § 5D1.3(b)(1). Farooq
repeatedly violated court orders throughout the case, including

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violating a family-court order of protection and contacting someone
in Pakistan about John Doe. Throughout the district court
proceedings, Farooq tried to publicize information about Jane Doe
and John Doe against the district court’s express orders. This
included sending letters to the President of the United States and
various government officials identifying both Jane Doe and John Doe
and sending copies of allegedly published articles to the district court
identifying Jane Doe and describing Farooq’s relationship with her.
Farooq also repeatedly alluded to or sought to introduce into
evidence articles that named the victims and disclosed potentially
harmful details about them. So the condition was closely related to
Farooq’s history of disseminating information about Jane Doe and
John Doe, including in defiance of court orders.
Third, the condition is narrowly tailored because it restricts
public dissemination of information only about Jane Doe or John Doe.
It is not a broad prohibition on speaking about the case or criticizing
the attorneys or the district court. See United States v. Coleman, No.
98-1299, 1999 WL 278878, at *2 (2d Cir. May 4, 1999) (explaining in
dicta that prohibiting the defendant from criticizing the government
“or anyone else” would “surely exceed a District Court’s discretion”).
The condition itself limits the restriction to “information about Jane
Doe or John Doe.” The district court explained the limited scope of
the condition during the sentencing hearing, noting that the purpose
was to “prevent Mr. Farooq from continuing to threaten [the victims]
through media.” App’x at 573. So the scope of the condition was
limited to information about Jane Doe and John Doe.
Fourth, the condition is limited in duration. Upon Farooq’s
guilty plea to the violation of supervised release, the district court

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imposed a new term of supervised release in November 2021 set to
expire in February 2023—lasting approximately three months.
Finally, the condition still allows Farooq to seek permission
from the district court to publish information about Jane Doe or John
Doe. In light of these limitations and the record before us, we
conclude that it was within the district court’s discretion to impose
this special condition.
III. CONCLUSION
We have considered all of Farooq’s remaining arguments and
have found them to be without merit. For the reasons set forth
above, the judgment of the district court is affirmed.

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