22-1022-cr United States v. Jimenez

UNITED STATES COURT OF APPEALS FOR THE SECOND CIRCUIT

SUMMARY ORDER

RULINGS BY SUMMARY ORDER DO NOT HAVE PRECEDENTIAL EFFECT. CITATION TO A SUMMARY ORDER FILED ON OR AFTER JANUARY 1, 2007, IS PERMITTED AND IS GOVERNED BY FEDERAL RULE OF APPELLATE PROCEDURE 32.1 AND THIS COURT’S LOCAL RULE 32.1.1. WHEN CITING A SUMMARY ORDER IN A DOCUMENT FILED WITH THIS COURT, A PARTY MUST CITE EITHER THE FEDERAL APPENDIX OR AN ELECTRONIC DATABASE (WITH THE NOTATION “SUMMARY ORDER”). A PARTY CITING A SUMMARY ORDER MUST SERVE A COPY OF IT ON ANY PARTY NOT REPRESENTED BY COUNSEL.

At a stated term of the United States Court of Appeals for the Second Circuit, held at the Thurgood Marshall United States Courthouse, 40 Foley Square, in the City of New York, on the 18th day of March, two thousand twenty-four.

Present:

GUIDO CALABRESI, EUNICE C. LEE, MYRNA PÉREZ, Circuit Judges. _____________________________________

UNITED STATES OF AMERICA,

Appellee,

v. No. 22-1022-cr

WILLIAM JIMENEZ, AKA Sealed Defendant 1, AKA Flip,

Defendant-Appellant. _____________________________________ For Appellee: JACOB R. FIDDELMAN, (David Abramowicz, on the brief), Assistant United States Attorneys, for Damian Williams, United States Attorney for the Southern District of New York, New York, NY.

For Defendant-Appellant: SARAH BAUMGARTEL, Federal Defenders of New York, Inc., New York, NY.

Appeal from an April 28, 2022 judgment of the United States District Court for the

Southern District of New York (Cote, J.).

UPON DUE CONSIDERATION, IT IS HEREBY ORDERED, ADJUDGED, AND

DECREED that the judgment of the district court is AFFIRMED in part and VACATED in part,

and the action is REMANDED for further proceedings consistent with this order.

Defendant-Appellant William Jimenez appeals from the district court’s judgment, entered

on April 28, 2022, following his guilty plea to one count of being a felon in possession of

ammunition, in violation of

(g)(1) and (2). Jimenez was sentenced to a term of

105 months’ imprisonment—the top of the applicable guidelines range—to be followed by three

years of supervised release. At sentencing, the district court stated that the conditions of

supervision would include “the standard conditions of supervised release,” which were set forth in

the Presentence Investigation Report (“PSR”). The district court also imposed six special

conditions without any explanation at sentencing, all but two of which had not been previously set

forth in the PSR.

2 On appeal, Jimenez challenges several of the special conditions imposed on him: a

condition requiring participation in a cognitive behavioral therapy program; a condition requiring

full-time employment (with an alternative condition requiring 20 hours of community service each

week if Jimenez is not employed or excused from employment); a condition permitting the

probation department to search Jimenez’s person, residence, and effects—including electronics—

upon reasonable suspicion; and a condition requiring disclosure of his financial information.

Jimenez argues that the district court erred because it failed to provide any reasons for

imposing these special conditions, and that the conditions themselves are overbroad, vague, and

delegate too much authority to the probation department. We remand for resentencing as to

several of the special conditions imposed on Jimenez given the district court’s lack of explanation.

* * *

“District courts possess broad discretion in imposing conditions of supervised release.”

United States v. Betts,

(2d Cir. 2018). They are “asked to carefully balance the

goals of supervised release while remaining mindful of the life-altering effects their judgments

have on defendants, their families, and their communities.” United States v. Sims,

(2d Cir. 2024). A district court may impose special conditions if they are “reasonably related”

to:

(A) the nature and circumstances of the offense and the history and characteristics of the defendant; (B) the need for the sentence imposed to afford adequate deterrence to criminal conduct; (C) the need to protect the public from further crimes of the defendant; and (D) the need to provide the defendant with needed educational or vocational training, medical care, or other correctional treatment in the most effective manner.

3 United States v. Carlineo,

(2d Cir. 2021) (quoting U.S. Sent’g Guidelines

Manual § 5D1.3(b)). A special condition must “involve no greater deprivation of liberty than is

reasonably necessary” to implement the statutory purposes of sentencing. United States v. Myers,

(2d Cir. 2005) (quoting U.S. Sent’g Guidelines Manual § 5D1.3(b)).

Moreover, when determining whether to impose special conditions, “[a] district court is

required to make an individualized assessment . . . and to state on the record the reason for

imposing it; the failure to do so is error.” Betts,

; see United States v. Bleau,

(2d Cir. 2019) (explaining that the district court’s failure to explain its rationale for

imposing a special condition constitutes plain error when “it is not obvious from the record why

such a condition was reasonably necessary” and, “[t]hus, there is a reasonable probability that the

error affected the outcome of [the defendant]’s sentence”) (internal quotation marks omitted); see

also Sims,

(sentencing courts are “required to make findings specific to the

defendant . . . that . . . justify including the special condition” at issue). If a district court does not

provide such an explanation, the condition at issue may be upheld “only if the district court’s

reasoning ‘is self-evident in the record.’” Betts,

(quoting United States v. Balon,

, 41 n.1 (2d Cir. 2004)).

Cognitive Behavioral Therapy Condition

Jimenez argues that the district court erred by imposing a special condition requiring

cognitive behavioral therapy because the condition was not explained by the court, is vague, and

improperly delegates judicial power to the probation department.

We agree that because the district court did not explain its reasoning for imposing the

cognitive behavioral therapy condition, and because justification for doing so is not self-evident

4 from the record, the condition must be vacated. 1 The record does not indicate that Jimenez has a

history of therapy or diagnosed mental health concerns which would necessitate therapy.

Additionally, based on the record, such mental health treatment was not suggested by probation,

the government, or the defense. Moreover, the undefined nature of the kind of program required

by this condition, while not the specific basis for our remand, raises questions about the meaning

of the condition. See Carlineo, 998 F.3d at 536–37 (finding that special condition requiring that

defendant participate in a restorative justice program was impermissibly vague given that the court

gave no guidance as to what specific activities would be involved or the required frequency of the

sessions, and because defendant was not put on notice as to what conduct would violate the

condition). Accordingly, we vacate this special condition and remand the case for the district

court to provide sufficient reasoning justifying this condition and explaining its requirements if

the court decides to reimpose it.

Condition Requiring 20 Hours of Community Service

Jimenez argues that the district court erred by imposing “without justification” the special

condition requiring him to complete 20 hours of community service for every week that he is

unemployed. Appellant’s Br. at 29.

While the Sentencing Guidelines allow the imposition of community service as a special

condition, see U.S. Sent’g Guidelines Manual § 5F1.3, here, the district court provided no

reasoning for its imposition. Nor is the district court’s reasoning as to the individualized need for

this condition self-evident in the record. Neither the probation department nor any party

1 Because we remand based on the district court’s lack of justification, we do not reach Jimenez’s claim of improper delegation.

5 requested community service, and the district court did not propose any outer limit on the total

number of community service hours to be performed. Without such a limit, Jimenez could exceed

the presumptive maximum of 400 hours of community service within as little as five months if he

is unable to secure employment after incarceration. See United States v. Parkins,

(2d. Cir. 2019) (explaining that the Guidelines “must be read to advise that courts should generally

refrain from imposing more than a total of 400 hours of community service as a condition of

supervised release”); U.S. Sent’g Guidelines Manual § 5F1.3 cmt. n.1 (noting that “[c]ommunity

service generally should not be imposed in excess of 400 hours”). Because the district court failed

to articulate any justification for the community service condition or delineate the outer bounds

for the number of hours, and because the reasoning is not self-evident, we remand to the district

court for resentencing.

Work Condition

Jimenez argues that the district court’s imposition of the standard condition that he “work

full time (at least 30 hours per week) . . . unless the probation officer excuses” him from doing so

conflicts with the court’s imposition of the special condition that he “seek and maintain full-time

employment” without exception. Appellant’s Br. at 36 (quoting App’x at 89–90). While these

two conditions are not inconsistent, the district court should clarify on remand which condition

takes precedence, as the special condition leaves no room for exception or excusal. See United

States v. Boyd,

, 52 (2d Cir. 2019) (summary order) (remanding to the district

court to clarify whether the special condition imposing a 40-hour work week requirement or the

standard condition imposing a 30-hour work week requirement takes precedence).

6 Search Condition

While an individual on supervised release has a diminished expectation of privacy, Balon,

, the district court provided no explanation for the broad search condition included

in Jimenez’s terms of supervised release. The court did not explain, nor is it self-evident from the

record, how a search condition of the broad scope at issue here—which includes search of

Jimenez’s home, belongings, and all electronics—is reasonably related to his offense of

conviction. 2 In light of the remand for elucidation of the other special conditions, the district

court may want to reconsider this expansive search condition or take care to explain how this

search condition is based on an individualized assessment of Jimenez, his history, or his offense.

See United States v. Griffin,

, 661, 661 n.5 (2d Cir. 2021) (summary order)

(noting “puzzlement” over how the electronic search condition is reasonably related to defendant’s

robbery conviction and remanding given the absence of an adequate explanation for its

imposition).

Financial Information Condition

Finally, Jimenez challenges the condition of supervision requiring him to provide the

probation department with “access to any and all requested financial information,” App’x at 89,

given that the court provided no explanation and that there was no apparent basis in the record for

2 The special condition reads: “You shall submit your person, and any property, residence, vehicle, papers, computer, other electronic communication, data storage devices, cloud storage or media, and effects to a search by any United States Probation Officer, and if needed, with the assistance of any law enforcement. The search is to be conducted when there is reasonable suspicion concerning violation of a condition of supervision or unlawful conduct by the person being supervised. Failure to submit to a search may be grounds for revocation of release. You shall warn any other occupants that the premises may be subject to searches pursuant to this condition. Any search shall be conducted at a reasonable time and in a reasonable manner.”

7 this condition. Jimenez also argues that the financial information condition is unconstitutionally

vague and overbroad. Because Jimenez’s offense conduct and personal history includes turning

to drug dealing to make money, it is self-evident from the record that the ability to review

Jimenez’s personal finances reasonably relates to the important interest of protecting the public

and deterring recidivism. See United States v. Brown,

(2d Cir. 2005) (holding

that a financial information condition is permissible where the supervisee has a history of making

money through illegal conduct). Nor is the financial information condition impermissibly vague.

The condition is “sufficiently clear to inform [Jimenez] of what conduct will result in his being

returned to prison,” United States v. MacMillen,

(2d Cir. 2008) (quoting United

States v. Simmons,

(2d Cir. 2003)), as it requires him to provide the probation

department only “requested” financial information. Accordingly, we conclude that the district

court did not err in imposing the financial information disclosure condition.

* * *

For the reasons set forth above, we instruct the district court to determine whether each of

the special conditions that were imposed without specific justification is reasonably related to the

factors set forth in the Sentencing Guidelines § 5D1.3(b) and, if so, to explain the reasons for

imposing the condition. We therefore AFFIRM the judgment in part, VACATE in part,

and REMAND for further proceedings consistent with this order.

FOR THE COURT: Catherine O’Hagan Wolfe, Clerk of Court

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