UNITED STATES OF AMERICA, Appellee, v. KENNETH THOMPSON, Defendant-Appellant.
No. 23-6943
United States Court of Appeals For the Second Circuit
DECIDED: JULY 10, 2025
August Term, 2024; SUBMITTED: JANUARY 16, 2025
Before: LIVINGSTON, Chief Judge, RAGGI and NARDINI, Circuit Judges.
Defendant-Appellant Kenneth Thompson was convicted, following a guilty plea, of one count of being a felon in possession of a firearm and ammunition in violation of
Thompson now appeals. Through counsel, he argues that the district court procedurally erred in imposing the three special conditions because it failed to make an individualized assessment of the need to impose them and failed to state on the record its reasons for doing so. In a separate pro se submission, Thompson also argues that his counsel before the district court was ineffective and that his guilty plea was involuntary. He therefore attempts to raise several challenges to his conviction and sentence, including that the district court erred in its Sentencing Guidelines calculation and that
We disagree. First, we conclude that Thompson waived any challenge to the mental health treatment condition because the record shows he consented to its imposition. Next, we hold that the district court made an individualized assessment of the need for the conditions, that the court adequately explained its reasons for imposing them, and that the court‘s reasoning was amply supported by the record. Lastly, we decline to consider Thompson‘s ineffective assistance of counsel claim, hold that the district court sufficiently ensured that his plea was voluntary and knowing, and hold that his remaining challenges to his conviction and sentence are barred by the appellate waiver of his plea agreement.
We therefore AFFIRM the judgment of the district court.
Amy Busa and Irisa Chen, Assistant United States Attorneys, for Breon Peace, United States Attorney for the Eastern District of New York, Brooklyn, NY, for Appellee.
Lawrence Gerzog, New York, NY, for Defendant-Appellant.
WILLIAM J. NARDINI, Circuit Judge:
Defendant-Appellant Kenneth Thompson was convicted, following a guilty plea, of one count of being a felon in possession of a firearm and ammunition in violation of
Thompson now appeals. He argues that the district court procedurally erred in imposing the conditions because it failed to make an individualized assessment of the need to impose them and failed to state on the record its reasons for doing so. Thompson also argues that his counsel before the district court was ineffective and that his plea was involuntary. He therefore attempts to raise several challenges to his conviction and sentence, including that the district court erred in its Guidelines calculation and that
We disagree. First, we conclude that Thompson waived any challenge to the mental health treatment condition because the record shows he consented to its imposition. Next, we hold that the district court made an individualized assessment of the need for the conditions, that the court adequately explained its reasons for imposing them, and that the court‘s reasoning was amply supported by the record. Lastly, we decline to consider Thompson‘s ineffective assistance of counsel claim, hold that the district court sufficiently ensured that his plea was voluntary and knowing, and hold that his remaining challenges to his conviction and sentence are barred by the appellate waiver of his plea agreement.
We therefore AFFIRM the judgment of the district court.
I. Background
On June 6, 2022, officers from the New York City Police Department (NYPD) reported to a subway platform in Jackson Heights, Queens, after a 911 caller reported that someone was pointing a gun at him on a subway car. As the E train pulled into the station, the NYPD officers saw that most passengers had moved to one end of a crowded subway car, to avoid a dispute occurring at the other end. The police found the caller, who said that Thompson had pulled a gun from his waistband and pointed it at him after the two got into an argument. The officers ordered Thompson to stop, but he fled, dropping a black plastic bag into a trash can as he ran. The officers caught Thompson, pulled the bag out of the garbage, and found inside a loaded Norinco .45 caliber automatic pistol and loose rounds of ammunition.
II. District Court Proceedings
On April 18, 2023, Thompson pled guilty, pursuant to a plea agreement, to one count of being a felon in possession of a firearm and ammunition in violation of
On May 22, 2023, the district court (Diane Gujarati, District Judge) accepted Thompson‘s guilty plea, finding that Thompson understood “his rights and the consequences of his plea of guilty,” that he “knowingly and voluntarily entered a plea of guilty,” and that “there [was] a factual basis for the plea.” Dist. Ct. Dkt. 23.
On June 29, 2023, the U.S. Probation Office issued a Presentence Investigation Report (PSR).2 The PSR described Thompson‘s offense conduct and detailed his criminal history, which included at least four felonies in New York state court, including (i) a 1982 conviction for rape in the first degree, (ii) 2000 conviction for attempted rape in the first degree, (iii) 1982 conviction for robbery in the first degree, and (iv) 1980 conviction for attempted burglary in the third degree. In addition, Thompson had a 2016 conviction for forcible touching, a misdemeanor.
The Probation Office also submitted a Sentence Recommendation, which proposed that the court impose a sentence of thirty-seven months of imprisonment and two years of supervised release with the following three special conditions: (i) a search condition authorizing a probation officer to conduct a reasonable search of Thompson‘s “person, property, house, residence, vehicle, papers, computers, . . . other electronic communications or data storage devices or media, or office,” upon “reasonable suspicion . . . that the defendant has violated a condition of his supervision and that the areas to be searched contain evidence of this violation“;
(ii) compliance with sex offender registration requirements; and (iii) participation “in a mental health treatment program, which may include participation in a treatment program for sexual disorders.”3 Probation Sentencing Recommendation at 1.
On August 7, 2023, Thompson appeared before the district court for sentencing. Thompson and his counsel affirmed that they had reviewed and discussed both the PSR and the Sentence Recommendation. Thompson again told the court that he was satisfied with his counsel‘s representation. After confirming there were no further objections to the PSR beyond what Thompson had included in his sentencing submission, the district court adopted the factual information included in the PSR. In light of the seriousness of Thompson‘s crime, his criminal history, his upbringing, and his health, the court sentenced Thompson to thirty-seven months in prison, followed by two years of supervised release.
The court stated it was imposing three special conditions of supervised release “[g]iven the nature and circumstances of [Thompson‘s] offense, and [his] history and characteristics.” Gov‘t App‘x at 88. The court imposed the search condition and sex offender registration condition largely as written in the Probation Officer‘s Sentence Recommendation. With respect to the mental health treatment condition to which Thompson had initially objected, the court indicated that it intended to impose a “more general” mental health-related condition than the one recommended by the Probation Office, id. at 50, and imposed the following condition, which made no mention of sexual disorders:
The defendant shall undergo a mental health evaluation, and if deemed necessary, participate in a mental health treatment program as approved by the U.S. Probation Department. The defendant shall contribute to the cost of such services rendered and/or any psychotropic medications prescribe[d] to the degree he is reasonably able[,] [a]nd shall cooperate in securing any applicable third-party payment. The defendant shall disclose all financial information and documents to the Probation Department to assess his ability to pay.
Id. at 89. The district court asked the parties if there were any objections to the conditions as imposed. Both said no.
Thompson now appeals his conviction and sentence.
III. Discussion
On appeal, Thompson argues that the district court procedurally erred by failing to make an individualized assessment when imposing the three special conditions of supervised release, and by failing to state on the record its reasons for imposing those conditions. Thompson also argues that his counsel before the district court was ineffective and that his plea was involuntary. He therefore attempts to raise several challenges to his conviction and sentence, including that the district court erred in its Guidelines calculation and that
a. Conditions of Supervised Release
We generally “review the imposition of conditions of supervised release for abuse of discretion.” United States v. Eaglin, 913 F.3d 88, 94 (2d Cir. 2019). When, as here, the defendant does not object to the conditions before the district court, we review for plain error. See United States v. Green, 618 F.3d 120, 122 (2d Cir. 2010); see also
“Our caselaw is clear that a district court retains wide latitude in imposing conditions of supervised release.” United States v. Lewis, 125 F.4th 69, 75 (2d Cir. 2025) (alteration adopted) (internal quotation marks and 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. Farooq, 58 F.4th 687, 694 (2d Cir.) (internal quotation marks and citation omitted), cert. denied, 143 S. Ct. 2677 (2023). Relevant sentencing factors include “‘the nature and circumstances of the offense and the history and characteristics of the defendant‘; ‘the need for the sentence imposed to afford adequate deterrence to criminal conduct‘; ‘the need to protect the public from further crimes of the defendant‘; and ‘the need to provide the defendant with needed educational or vocational training, medical care, or other correctional treatment in the most effective manner.‘” United States v. Betts, 886 F.3d 198, 202 (2d Cir. 2018) (quoting
Additionally, “[a] district court is required to make an individualized assessment when determining whether to impose a special condition of supervised release, and to state on the record the reason for imposing it; the failure to do so is error.” Betts, 886 F.3d at 202. “In the absence of such an explanation, we may uphold the condition imposed only if the district court‘s reasoning is self-evident in the record.” Id. (internal quotation marks and citation omitted). When the reason for a special condition “is self-evident in the record . . . and the condition[ ] meet[s] the purposes of supervised release, any error . . . in this respect is harmless.” United States v. Balon, 384 F.3d 38, 41 n.1 (2d Cir. 2004).
1. Mental Health Treatment Condition
We first consider the district court‘s imposition of the mental health treatment condition. We conclude that Thompson has waived any challenge to the condition‘s imposition. At sentencing, the district court explained that it planned to impose a more general mental health treatment condition that (unlike the one recommended by the Probation Office) made no mention of treatment for sexual disorders, but before doing so, it directed defense counsel to consult with his client. Thompson‘s counsel then reported that he had spoken with his client and that Thompson “knows the good in counseling” and therefore “ha[d] no issue with” what the district court was “suggesting.” Gov‘t App‘x at 75. A defendant who expresses agreement with a special condition of supervised release waives any challenge to that condition on appeal. See United States v. Spruill, 808 F.3d 585, 597 (2d Cir. 2015) (“[T]his court has recognized waiver where a party actively solicits or agrees to a course of action that he later claims was error.“). Thompson‘s consent to the district court‘s proposed special condition in lieu of the condition recommended by the Probation Office “constitutes a true waiver which . . . negate[s] even plain error review.” United States v. Quinones, 511 F.3d 289, 321 (2d Cir. 2007) (internal quotation marks and citation omitted).
Even if Thompson‘s challenge to the condition had not been waived but merely forfeited, we identify no error-much less plain error-because the court‘s remarks, in their totality, were sufficient to satisfy “the requirement that [a] court must conduct an individualized assessment . . . and must state on the record the reason for imposing [a special condition].” United States v. Sims, 92 F.4th 115, 126 (2d Cir. 2024). The district court said it was ordering the special conditions given Thompson‘s personal “history and characteristics.” Gov‘t App‘x at 88. Just moments earlier, the district court had highlighted Thompson‘s difficult upbringing and background, stating that “[t]he record reflects the defendant has had struggles during his life, including from an early age. He has suffered abandonment and abuse, and I have considered those.” Id. at 85. The district court went on to tailor the mental health treatment condition, omitting the Probation Office‘s recommended focus on sexual disorder treatment and instead imposing a more general mental health treatment program because “[t]hat [could] be very helpful to [Thompson].” Id. at 74. We have previously stated that “[a] court may require as a special condition of [supervised release] that a defendant participate in a mental health program ‘[i]f the court has reason to believe that the defendant is in need of psychological or psychiatric treatment.‘” See United States v. Peterson, 248 F.3d 79, 84 (2d Cir. 2001) (third
Indeed, the record makes clear that the district court was presented with, and considered, an ample basis for imposing the mental health treatment condition. Thompson admitted he was diagnosed with anxiety as a young adult and was prescribed an antidepressant while serving a sentence for a previous conviction. He also stated at his plea hearing that he “was at a psych ward for the state . . . for stress and anxieties.” Gov‘t App‘x at 13. At sentencing, in arguing for a downward departure, defense counsel emphasized Thompson‘s “pretty horrible childhood,” stating that “it‘s difficult to imagine a tougher start in life,” id. at 65-66, and urged the court to consider the emotional and physical abuse Thompson had suffered at a young age. As noted above, when the court gave Thompson the opportunity to discuss the mental health treatment condition, defense counsel stated that “after speaking with Mr. Thompson . . . [h]e knows the good in counseling, and to what you‘re suggesting, he has no issue with [it].” Id. at 75. Thompson‘s own admissions on the record of his struggles with mental health and his acknowledgment of the benefit of treatment fully support the district court‘s imposition of the condition. See United States v. Arguedas, 134 F.4th 54, 70 (2d Cir. 2025) (finding that the reasoning for a mental health treatment condition was “self-evident in the record” given the defendant‘s “history of . . . struggles with mental health“). Thus, based on Thompson‘s statements to the Probation Office, at his plea hearing, and at sentencing, the condition is reasonably related to his history and characteristics.
2. Search Condition
We next consider the district court‘s imposition of the search condition. As stated above, the court said it was imposing all three special conditions of supervised release given “the nature and circumstances of [Thompson‘s] offense, and [his] history and characteristics.” Gov‘t App‘x at 88. In this case, the court‘s remark adequately demonstrated the district court‘s individualized assessment of the need for the search condition, and explained its basis for imposing it. As we have previously explained, “[t]he court [is] under no obligation . . . to pick through every condition and explain, point-by-point, how each was responsive to the offending conduct.” United States v. Kunz, 68 F.4th 748, 760 (2d Cir. 2023). “The specific obligation to state on the record the reason for imposing a special condition is merely a subset of the broader requirement to state in open court the reasons for the particular sentence . . . [a]nd that requirement leaves the appropriateness of brevity or length to the judge‘s own professional judgment.” United States v. Lawrence, 139 F.4th 115, 124 (2d Cir. 2025) (internal quotation marks and citation omitted); see also United States v. Jenkins, 854 F.3d 181, 194 (2d Cir. 2017) (“[A] district court is under no obligation to provide elaborate reasons for the sentence it imposes.“). Just as we have held that a district court typically need not separately articulate its reasons for imposing a term of supervised release when it has already generally stated its reasons for imposing a term of imprisonment, see United States v. Williams, 998 F.3d 538, 541-42 (2d Cir. 2021), a district court generally need not articulate separate reasons for imposing every single special condition where it has already explained the overall reasons for its sentencing decision. We therefore conclude that the district court demonstrated its individualized assessment of the search condition when it stated that, in imposing these special conditions, it was taking into account the nature and circumstances of Thompson‘s
The court‘s reliance on these factors was amply supported by the record here, given Thompson‘s history of recidivism and the nature of his past crimes. The court pointed out that Thompson has a “serious[,] long and varied criminal history,” which includes “convictions for rape, attempted rape, forcible touching, robbery and burglary.” Gov‘t App‘x at 84. The court noted that despite his prior “sentences, some lengthy,” Thompson remained undeterred from committing further crimes, including two crimes that he had committed more recently. Id. at 84-85. The record also reflects that Thompson‘s attempted rape offense was committed while he was on parole supervision for his conviction of first-degree rape, casting additional doubt on his ability to conduct himself in good faith while on supervised release. “Under these circumstances, the special search condition . . . is necessary for ensuring the effectiveness of supervision.” United States v. Robinson, 134 F.4th 104, 112 (2d Cir. 2025). “[I]t operates as an important means for enforcing the court‘s other conditions and enabling the detection of evidence of supervised release violations.” Id. For these reasons, we find that the condition is reasonably related to Thompson‘s history and characteristics and the need for deterrence, and it meets the purposes of supervised release.
Thompson argues that the breadth of the search condition imposed here, which includes searches of electronic devices, “cannot possibly be viewed as in compliance with this Court‘s precedents.” Appellant Br. at 14-15. We disagree. We recently upheld an identical search condition containing an electronic search provision in United States v. Robinson. See 134 F.4th at 108, 112. In that case, we held that despite the district court‘s failure to conduct an individualized assessment when imposing the condition,4 the need for the condition was self-evident in the record given the defendant‘s “criminal history” and “extensive history of recidivism.” Id. at 111. The imposition of an identical electronic search provision in this case is therefore
entirely appropriate for similar reasons. Additionally, in Robinson we stated that “the justification for [the] electronic search portion of the condition would be even more apparent if [the defendant‘s] [underlying or prior] convictions involved sex offenses.” Id. at 112 (referencing
Thompson also argues that the search condition implicates significant liberty interests that the district court failed to consider. We conclude that this argument, too, is without merit. This Court has
We take this opportunity to emphasize again that a district court can reasonably conclude that such search conditions are “necessary for ensuring the effectiveness of supervision,” Robinson, 134 F.4th at 112, and that “both electronic and non-electronic search conditions are often crucial” for doing so, even where the record does not indicate electronic devices were misused in the underlying crime of conviction or criminal history, id. at 112 n.4. As we have previously observed, district courts exercise their discretion to “impose terms of supervised release in nearly every federal sentence, despite being required to do so only in certain limited circumstances.” Sims, 92 F.4th at 119-20. This demonstrates a clear consensus amongst the district courts-who are on the front lines working with released defendants-that supervised release is essential for “assist[ing] individuals in their transition to community life.” United States v. Johnson, 529 U.S. 53, 59 (2000). The courts have an “overwhelming interest” in monitoring those on supervised release to “reduc[e] recidivism and thereby promot[e] reintegration and positive citizenship” among supervisees. Samson v. California, 547 U.S. 843, 853 (2006). We have therefore recognized that in overseeing individuals on supervised release, probation officers must be given “considerable investigative leeway,” United States v. Reyes, 283 F.3d 446, 457 (2d Cir. 2002), because in bringing a supervisee‘s offending conduct to the attention of the court, they act as the “eyes and ears” of the judge, id. at 455. A search condition, like the one imposed here, can be an important tool for probation officers to carry out that mandate. To strike such a condition here would improperly intrude upon the district court‘s broad discretion to determine how best to monitor Thompson‘s adherence to conditions of release and therefore impair the court‘s ability to enforce those conditions.
We also emphasize again the limited nature of the search condition here. The condition requires that the Probation Office have (i) reasonable suspicion that Thompson has violated a condition of his supervised release; and (ii) reasonable suspicion that evidence of that violation is to be found in one of the specified areas. Both the justification for the search and the limitation on the search parameters directly relate to the district court‘s need to
3. Sex Offender Registration Condition
Finally, with respect to the sex offender registration condition, we conclude for the same reasons stated above that the district court made an individualized assessment in imposing the condition and that this condition, too, is supported by the record. District courts have broad discretion to impose certain conditions of supervised release related to a defendant‘s sexual behavior even when the present conviction does not involve a sexual offense. See United States v. Dupes, 513 F.3d 338, 343-44 (2d Cir. 2008) (upholding conditions requiring the defendant to, inter alia, attend sex offender treatment and register as a sex offender where his conviction was for securities fraud). Here, Thompson had multiple prior convictions for sex offenses, including rape, attempted rape, and forcible touching. Thompson does not dispute that the law already requires him to register as a sex offender on the New York State Sex Offender Registry. The condition therefore simply requires Thompson to comply with legal obligations to which he is already subject. It is hardly a revolutionary proposition to require a supervisee to obey the law. The condition was therefore entirely appropriate.
Accordingly, we affirm the district court‘s imposition of the special conditions of supervised release.
b. Ineffective Assistance of Counsel
Thompson contends for the first time on appeal that his trial counsel was constitutionally ineffective and that his conviction should therefore be vacated. He argues pro se that trial counsel failed to raise certain stronger issues over weaker ones, failed to appeal the denial of his bail application, waived a preliminary hearing, and failed to object to certain portions of the PSR, even though he twice confirmed at his plea hearing that he was fully satisfied with his counsel‘s representation.
When an ineffective assistance of counsel claim is raised on direct appeal, the Court may: (1) decline to hear the claim and permit the appellant to raise the issue under
Because Thompson did not raise his ineffective assistance claim in the district court, and did not submit to this Court the transcript of the proceeding denying his application for bail, “there is no[t a sufficient] record that would permit [it] to be assessed on this appeal.” Id. at 97. His arguments are based primarily on his attorney‘s strategic decisions, such as the decision to waive preliminary hearings or advance certain arguments. But the record tells us nothing about why counsel made those choices, much less why they could be considered deficient or prejudicial in any way. We therefore decline to adjudicate the claim on this appeal. Thompson is free to raise the claim in the district court-which is “best suited to developing the facts necessary to determining the adequacy of representation“-through a motion under
c. Appellate Waiver
Thompson raises additional pro se challenges to his sentence and conviction, including that the district court erred in its Guidelines calculation and that
“This Court has repeatedly held that a knowing and voluntary waiver of the right to appeal a sentence is presumptively enforceable.” United States v. Ojeda, 946 F.3d 622, 629 (2d Cir. 2020). “[T]he exceptions to this rule occupy a very circumscribed area of our jurisprudence.” United States v. Borden, 16 F.4th 351, 354-55 (2d Cir. 2021) (internal quotation marks and citation omitted). In certain cases, “a defendant may have a valid claim that the waiver of appellate rights is unenforceable, such as [1] when the waiver was not made knowingly, voluntarily, and competently, [2] when the sentence was imposed based on constitutionally impermissible factors, such as ethnic, racial or other prohibited biases, [3] when the government breached the plea agreement, or [4] when the sentencing court failed to enunciate any rationale for the defendant‘s sentence, thus amounting to an abdication of judicial responsibility subject to mandamus.” United States v. Gomez-Perez, 215 F.3d 315, 319 (2d Cir. 2000) (alteration adopted) (internal quotation marks and citations omitted).
Thompson argues that his plea was unknowing because the district court failed to inform him that to prosecute under
United States v. Cook, 722 F.3d 477, 481 (2d Cir. 2013). “In assessing the likely effect of a Rule 11 error, we are to examine the entire record.” United States v. Torrellas, 455 F.3d 96, 103 (2d Cir. 2006).
We conclude that the plea agreement therefore bars Thompson‘s remaining challenges to his sentence and conviction.5 His constitutional claim and challenge to the district court‘s Guidelines calculation are explicitly barred by the language of the appellate waiver, which states that Thompson “agrees not to file an appeal or otherwise challenge . . . [his] conviction or sentence” including by raising “any argument that . . . the statutes to which [he] is pleading guilty are unconstitutional.” Gov‘t App‘x at 3; see also Cook v. United States, 84 F.4th 118, 125 (2d Cir. 2023) (holding that a valid waiver precludes a post-conviction claim that a defendant‘s conviction was predicated on an unconstitutional statute). Though we have left open the question of whether a defendant can challenge the constitutionality of his conviction on appeal notwithstanding a waiver in the rare circumstance when there has been a “complete miscarriage of justice,” Cook, 84 F.4th at 125 n.4 (internal quotation marks and citation omitted), there has been no miscarriage of justice here. Thompson argued before the district court that
withdraw his guilty plea before the court based on a challenge under Bruen. And in any case, his argument would be foreclosed by our Court‘s recent decision in Zherka v. Bondi, 140 F.4th 68 (2d Cir. 2025), which rejected an identical argument and upheld the constitutionality of
IV. Conclusion
In sum, we hold as follows:
-
Thompson‘s consent to the mental health treatment condition waives any challenge to that condition on appeal. - The district court‘s explanation that it was imposing the special conditions given the nature and circumstances of Thompson‘s offense, as well as his history and characteristics, manifested both an individualized assessment of the need for each condition and a statement of its reasons for their imposition. The district court therefore did not procedurally err in imposing the conditions.
- The district court‘s reasons for imposing the conditions were amply supported by the record.
- The district court was not required to justify the inclusion of a particular place or thing under the defendant‘s custody or control in the search condition, where the condition requires reasonable suspicion that the defendant has violated a condition of his supervised release and that evidence of a violation would be found there.
- We decline to consider Thompson‘s claim of ineffective assistance of counsel, which is raised for the first time on appeal.
- The district court ensured that Thompson‘s plea was voluntary and knowing, and consequently his remaining challenges to his conviction and sentence are barred by the appellate waiver in his plea agreement.
Accordingly, we AFFIRM the district court‘s judgment.