United States of America v. Sims
No. 21-3015
United States Court of Appeals for the Second Circuit
Decided: February 5, 2024
August Term 2022
Submitted: January 13, 2023
UNITED STATES OF AMERICA,
Appellee,
v.
DEWEY K. SIMS,
Defendant-Appellant.
No. 21-cr-52, Mae D‘Agostino, District Court Judge.
Before: CALABRESI, PÉREZ, and NATHAN, Circuit Judges.
On appeal from a sentencing judgment entered in the United States District Court for the Northern District of New York (D‘Agostino, J.).
Defendant-Appellant Dewey K. Sims pleaded guilty to possessing a firearm after a prior felony conviction, in violation of
VACATED IN PART AND REMANDED.
James P. Egan, Assistant Federal Public Defender, Federal Public Defender‘s Office, Northern District of New York, Syracuse, NY, for Defendant-Appellant.
Emmet O‘Hanlon, Assistant United States Attorney for Carla B. Freedman, United States Attorney for the Northern District of New York, Albany, NY, for Appellee.
MYRNA PÉREZ, Circuit Judge:
In this apрeal, Defendant-Appellant Dewey K. Sims challenges the district court‘s imposition of a “special condition”1 of supervised release prohibiting him from “associat[ing] with any member, associate, or prospect” of any “criminal gang, club, or organization.” Appellant‘s App‘x (“App‘x“) at 92.
When imposing a sentence that includes a term of supervised release, sentencing courts are given broad discretion to attach “special conditions,” which constrain the defendant‘s behavior. But the court‘s authority to impose such conditions is not boundless. One limitation is that the sentencing court‘s explanation of its decision to impose the special condition must be supported by the record. In this case, the sentencing court‘s reason for imposing the special condition was neither adequately explained nor supported by the record, and therefore we vacate the condition and remand the case for further proceedings.
DISCUSSION
After a criminal defendant is found guilty of an offense, the court must turn to the important task of determining an appropriate sentence. Courts impose terms of supervised release in nearly every federal sentence, despite being required to do
When a court imposes a term of supervised release, it also determines what conditions or restrictions are appropriate for that defendant. Courts are given broad latitude to design their own “special conditions,” so long as the courts, among other things, consider the goals of sentencing, including the need for the sentence to provide adequate deterrence, protect the public, and provide the defendant with needed services. See
Here, the district court imposed two conditions of supervised release that limited Sims‘s ability to associate with certain groups. The first is a standard condition listed under U.S.S.G. § 5D1.3(c), which presumptively applies to all terms of supervised release. It directs that Sims not “communicate or interact with someone the defendant knows is engaged in criminal activity” and further that “[i]f the defendant knows someone has been convicted of a felony, the defendant shall not knowingly communicate or interact with that person without first getting the permission of the probation officer” (the “Standard Non-Association Condition“). See U.S.S.G. § 5D1.3(c)(8); see also App‘x at 91.
The second condition prohibits Sims from “associat[ing] with any member, associate, or prospect of the Jungle Junkies, or any other criminal gang, club, or organization” (the “Special Non-Association Condition“). App‘x at 92. In this case, we primarily review the court‘s imposition of the Special Non-Association Condition.
I. Factual Background2
This sentencing appeal arises from Sims‘s guilty plea for possession of a firearm as an individual previously convicted of a felony, in violation of
A. The Presentence Report and Parties’ Submissions
Sims entered a guilty plea, and the United States Probation Office prepared a Presentence Investigation Report (“PSR“) for sentencing. As relevant here, the PSR noted that the National Crime Information Center (“NCIC“) records identified Sims as a member of the Jungle Junkies criminal gang, which Sims has consistently denied. Sims‘s criminal history does not contain
The PSR also mentioned Sims‘s tattoos—including a sleeve displaying the names of Sims‘s friends who passed away during his childhood—and that reports in the RICO conspiracy case had identified some of those individuals as Jungle Junkies members. During his presentencing interview, Sims informed the Probation Office that he had grown up with the individuals on his sleeve but contended that he “was friends with them long before they were ever charged” as Jungle Junkies in the RICO case.
The Probation Office recommended a sentence that included a term of supervised release and three speсial conditions, including the Special Non-Association Condition. In his sentencing submission to the court, Sims objected to the proposed Special Non-Association Condition and the portions of the report describing him as having any gang affiliation. Sims further argued that the Standard Non-Association Condition, prohibiting him from communicating or interacting with individuals involved in criminal conduct or with known felons, would achieve the same sentencing goals as the recommended Special Non-Association Condition. Therefore, Sims contended that the proposed Special Non-Association Condition was more restrictive than necessary.
B. The Sentencing Hearing
At the beginning of the sentencing hearing, the district court adopted thе factual information in the PSR, without explanation or specifically addressing Sims‘s objections. After doing so, it asked whether Sims had any ongoing objections to the facts in the PSR, to which Sims‘s attorney responded: “No, your Honor. Just the objections noted in the sentencing memo concerning the recommended conditions of supervision . . . .” App‘x at 70.
When it was time for Sims to be heard, his attorney argued that: (1) the Special Non-Association Condition was unrelated to the factors under
The court sentenced Sims to 33 months’ imprisonment to be followed by three years of supervised release. The court granted Sims‘s placement request and recommended that he be placed in a facility as close to Pennsylvania as possible. As to the term of supervised release, the court imposed fifteen “standard” conditions,3 one of which was the Standard Non-Association
The court turned to a discussion of the special conditions, stating that it found them:
necessary and justified based upon the nature of the instant offense as well as your history and characteristics as the defendant as outlined in detail in the presentence report and to promote rehabilitation of the defendant.
It is noted that the special conditions were previously disclosed to the parties and are included in the presentence report. And this afternoon I have heard arguments both for the special conditions and against the special conditions.
. . . .
As far as the condition that the defendant not associate with any gang members, I know what I know from reading the presentence investigation report, which does indicate, according to the National Crime Information Center, that this defendant has had some gang affiliation.
You know, if most of the gang members have passed away or if indeed it‘s true that Mr. Sims was not associated with the gang, this will be an easy condition for him to follow, I would think. But, again, I‘m going to err on the side of caution because I think it will promote his rehabilitation if indeed he has participated in gang activity . . . .
App‘x at 81-82. This timely appeal followed.
II. Analysis
On appeal, Sims challenges the Special Non-Association Condition on two grounds: (1) the record fails to indicate that the condition is reasonably related to the purposes of supervised release and constitutes a greater infringement on Sims‘s liberty than is necessary; and (2) the condition was impermissibly vague. We vacate and remand the Special Non-Association Condition based on the first argument. Accordingly, we need not reach the second.
A. Standard of Review
We review special conditions of supervised release for both procedural and substantive reasonableness. United States v. Eaglin, 913 F.3d 88, 94 (2d Cir. 2019). Sims challenges the procedural reasonableness of his sentence, and because he preserved his objection in the district court, we review for abuse of discretion. See United States v. Betts, 886 F.3d 198, 201 (2d Cir. 2018). As with our review of other aspects of a sentence, “[t]he procedural inquiry looks to whether the sentencing judge has properly accounted for the factors that constrain its sentencing discretion; substantive reasonableness examines whether, after accounting for those constraints, the district court‘s exercise of its discretion can be ‘located within the range of permissible decisions.‘” United States v. Kunz, 68 F.4th 748, 759 (2d Cir. 2023) (quoting United States v. Matta, 777 F.3d 116, 124 (2d Cir. 2015)).
B. Applicable Law
When deciding whether a term of supervised release is appropriate—and if
If the court decides a term of supervised release is appropriate, it must also determine what conditions should apply.
We highlight in greater detail below certain of the requirements a court must satisfy when imposing special conditions of supervised release.
1. The court must conduct an individualized assessment and find that the special condition is reasonably related to the sentencing factors.
Our precedent makes clear that for the imposition of special conditions of supervised release to be procedurally reasonable, “a District Court must ‘make an individualized assessment when determining whether to impose a speсial condition of supervised release, and . . . state on the record the reason for imposing it,‘” and “‘[a]ny explanation provided by the District Court must be adequately supported by the record.‘” Eaglin, 913 F.3d at 94 (quoting Betts, 886 F.3d at 202).
In other words, the court is required to make findings specific to the defendant, connecting those findings to the applicable § 3553(a) factors that would justify including the special condition in this case.4 See United States v. Salazar, No. 22-1385-cr, 2023 WL 4363247, at *3 (2d Cir. July 6, 2023) (vacating judgment where district court “did not make individualized
“There must be a reasonable relationship between the factors considered by the district court in the individualized assessment and the special condition of release being challenged.” United States v. Haverkamp, 958 F.3d 145, 151 (2d Cir. 2020) (citation omitted); see
2. The court must explain its reasoning, which must be supported by the record.
The court‘s individualized assessment, and its explanation for imposing the special condition following that assessment, “must be adequately supported by the record.” Eaglin, 913 F.3d at 94. If the court fails to provide an explanation, we may uphold the special condition only if the court‘s reasoning is “self-evident in the record.” Betts, 886 F.3d at 202 (quoting United States v. Balon, 384 F.3d 38, 41 n.1 (2d Cir. 2004)).5
3. The condition must not imposе a greater deprivation of liberty than reasonably necessary to accomplish sentencing objectives.
The court must also consider how a special condition will impact any cognizable liberty interests in light of any sentencing objectives.
4. The condition must be consistent with any pertinent policy statements issued by the Sentencing Commission.
In addition, courts are required to consider the Sentencing Commission‘s policy statements on, among other things, the appropriate use of conditions of supervised release.
5. The court must orally pronounce the condition in open court.
Under
6. The condition must be sufficiently clear.
“[A] defendant has a due process right to conditions of supervised release that are sufficiently clear to inform him of what conduct is prohibited so that he may act accordingly.” United States v. Carlineo, 998 F.3d 533, 536 (2d Cir. 2021). The condition must give the defendant “notice as to what conduct could trigger a charge of violating the condition,” including “what he must do, [and] for how long, to ensure he will not be re-incarcerated.” Id. at 537 (citation omitted).6 “A condition is too vague if it requires a reasonable person to speculate as to its meaning.” Id. at 536 (citation omitted). However, “[c]onditions need not be cast in letters six feet high, or describe every possible permutation, or spell out every last, self-evident detail.” United States v. Reeves, 591 F.3d 77, 81 (2d Cir. 2010) (ellipses omitted) (quoting Johnson, 446 F.3d at 280).
7. The condition must not result in the court exceeding its ability to delegate decision-making authority to Probation.
While a district court may delegate to the Probation Office decision-making
C. Application
We focus our discussion on the requirement that the court must conduct an individualized assessment as to whether the special condition is reasonably related to the applicable § 3553(a) sentencing factors and must state on the record the reason for imposing it. See Betts, 886 F.3d at 202. Of course, when the court‘s explanation for imposing the special condition is lacking, we may uphold it only if the court‘s reasoning is “self-evident” from the record. Id. This guiding principle assumes heightened import in situations such as the one we have here, where the condition being imposed impacts the defendant‘s liberty interest significantly.
The special condition central to this case falls within a particular subcategory of non-mandatory conditions of supervised release which we refer to as “non-association” conditions. Non-association conditions order the defendant to “refrain from frequenting specified kinds of places or from associating unnecessarily with specified persons.”
During the sentencing hearing, the court stated that it was imposing all three of the special conditions suggested by the Probation Office based on Sims‘s offense, his history and characteristics as described in the PSR, and the promotion of rehabilitation. And as mentioned previously, one such special condition was a non-association condition—the Special Non-Association Condition. Acknowledging that the Special Non-Association Condition need only be related to one of the sentencing factors, see McLaurin, 731 F.3d at 262, we review each of these factors below.
1. The Nature and Circumstances of the Offense
First, turning to the nature and circumstances of the offense,
In that way, this case is unlike many of our other non-association cases, where the record established that the prohibited association had some relationship to the crime of conviction. See, e.g., United States v. Bolin, 976 F.3d 202, 210-13 (2d Cir. 2020) (collecting cases).
For example, in Bolin, the defendant pled guilty to making false statements to the FBI Joint Terrorism Task Force during an investigation into threatening content that he had posted on social media. Id. at 211-13. The defendant‘s social media posts had explicitly endorsed white supremacist violence against Jews, Muslims,
Likewise, in a non-precedential case, United States v. Rakhmatov, Nos. 21-151(L), 21-167(Con), 2022 WL 16984536, at *3 (2d Cir. Nov. 17, 2022) (citing Betts, 886 F.3d at 202); see also United States v. Schiff, 876 F.2d 272, 276 (2d Cir. 1989) (“It is not an abuse of discretion for a district court to require that a person convicted of attempted tax evasion not associate with people who encourage tax evasion. We have upheld probation conditions that restrict a person‘s liberty before, when, as here, those conditions bear a reasonable relation to the crime of which the defendant stands convicted.“). In this case, however, there is no nexus between the underlying offense and the Special Non-Association Condition.
2. The History and Characteristics of the Defendant
Next, turning to Sims‘s history and characteristics,
Sims has never been charged with or convicted of a crime related to, or on behalf of, the Jungle Junkies or any other gang, gang member, or associate. Though the district court referred to Sims‘s presence in the NCIC database, it noted it was imposing the Special Non-Association Condition, even “if most of the gang members have passed away or if indeed it‘s true that Mr. Sims was not associated with the gang.” App‘x at 82. It justified imposing the Special Non-Association Condition in any event by explaining that it “will be аn easy condition” for Sims to follow. Id. But that explanation casts doubt on whether the Special Non-Association Condition should be imposed in this case. As we have discussed, we may only uphold a special condition unexplained by the district court if the court‘s justification for imposing the condition is “self-evident in the record.” Betts, 886 F.3d at 202. If Sims indeed had no association to a gang, as he contends and as posited by the district court, it is neither apparent nor self-evident how his history and characteristics would be reasonably related enough to support imposing the Special Non-Association Condition.
The reasonableness of the Special Non-Association Condition in connection with Sims‘s pаrticular history and characteristics is even less clear given that Sims had already requested (and the court granted) placement out of state, well away from any members of the Jungle Junkies with whom he might be acquainted. Further, the court imposed, and Sims had no objection to, the Standard Non-Association Condition, which prohibited Sims from communicating or interacting with individuals engaged in criminal activity or with known felons. Nonetheless, the court did not acknowledge Sims‘s argument that the Standard
Of course, there will be times when a sentencing court‘s decision to impose both the Standard Non-Association Condition and a condition like the Special Non-Association Condition here is appropriate, given a defendant‘s history and characteristics. In this case, however, it was not. Most notably, we have often upheld the imposition of both conditions when the defendant admitted and/or did not contest his relationship to the prohibited group.
Three recent non-precedential decisions where we upheld a special condition similar to the one at issue here illustrate how critical the defendant‘s history and circumstances are to assessing the appropriateness of the special condition. For example, in United States v. Floyd, we upheld a special condition prohibiting the defendant from frequenting any place where criminal gangs may meet pursuant to a non-exclusive prohibition list provided by the probation department. See 840 F. App‘x at 628, aff‘g No. 15-CR-0287-12(WFK), 2018 WL 3918166, at *3 (E.D.N.Y. Aug. 14, 2018). In that case, the district court relied on, among other things, the undisputed fact of the defendant‘s history of being affiliated with multiple gangs. 2018 WL 3918166, at *3. In LoFranco v. United States Parole Commission, we affirmed a condition prohibiting the defendant from associating with chapters of the Hell‘s Angels Motorcycle Club, of which he and his co-conspirators were members and in which he held a high-ranking leadership position. 175 F.3d 1008 (2d Cir. 1999) (unpublished), aff‘g 986 F. Supp. 796, 804-08 (S.D.N.Y. 1997).
In United States v. Marshall, we upheld a special condition identical to the one imposed on Sims. 808 F. App‘x 11, 14 (2d Cir. 2020). But in that case, the defendant admitted gang membership in an interview with the FBI, then later denied it. Id. Thus, in that context, we cited with approval the Ninth Circuit‘s view that “[a] condition barring contact with an organization may be substantively reasonаble even if the defendant denies membership.” Id. (alteration in original) (quoting United States v. Evans, 883 F.3d 1154, 1161 (9th Cir. 2018)).
In this case, however, Sims has consistently denied any affiliation with the Jungle Junkies or any other criminal gang, and the PSR provides nothing but a conclusory statement classifying him as a gang member. In fact, Sims‘s affiliation with the Jungle Junkies was so unestablished that even the district court acknowledged that Sims may not have been affiliated with the Jungle Junkies at all. Given the doubt surrounding Sims‘s affiliation with the Jungle Junkies, clarification from the district court as to why the condition is warranted in this particular case is necessary.
3. The Need for the Sentence to Deter Criminal Conduct, Protect the Public, and Provide the Defendant with Rehabilitative Treatment
Turning to the sentencing goals listed under
Further, the court provided little explanation for why imposition of the Special
If the goal is to, as a general matter, deter criminal conduct and prevent recidivism by prohibiting interactions with those involved in criminal behavior, the same is true of every case. Indeed, that goal is addressed and furthered by a Standard Non-Association Condition, which is usually already included in a defendant‘s term of supervised release. See Betts, 886 F.3d at 203 (vacating a special condition prohibiting all alcohol use and noting, among other things, that “[g]iven the factual record below,” the standard condition рrohibiting “excessive use” was “sufficient to further the objectives of sentencing“); see also United States v. Reed, 421 F. App‘x 113, 116 (2d Cir. 2011) (vacating special condition and remanding, with the direction that “[i]n determining whether special conditions are indeed necessary, we specifically direct the court to consider whether ‘standard’ condition U.S.S.G. § 5D1.3(c)(7), also imposed by the court‘s judgment, adequately addresses the court‘s alcohol and substance abuse concerns given the record in this case“).
III. Conclusion
There may be good reasons for imposing the Special Non-Association Condition. But because we have determined that the reasonableness of imposing the Special Non-Association Condition is not self-evident from this record as it stands, vacating the Special Non-Association Condition and remanding is appropriate so that the district court may provide the necessary justification or further develop the record to support the imposition of the special condition.7
We have considered all of the parties’ remaining arguments on appeal and have found them to be without merit. The judgment of the district court is VACATED IN PART with respect to the Special Non-Association Condition, and the case is REMANDED for further proceedings consistent with this opinion.