### In the 

# United States Court of Appeals For the Seventh Circuit

____________________ No. 19-1300
U NITED S TATES OF A MERICA , Plaintiff-Appellee
,

v.

S HAWN A. L EE , Defendant-Appellant

.

____________________ Appeal from the United States District Court for the Central District of Illinois. No. 3:18-cr-30011 — Sue E. Myerscough
, Judge

.

____________________

A RGUED S EPTEMBER 26, 2019

— D ECIDED F EBRUARY 18, 2020

— A MENDED J UNE 9, 2020

____________________

Before B AUER , M ANION , and S T

. E VE , Circuit Judges

. M ANION , Circuit Judge . Shawn Lee sold a staggering amount of ice methamphetamine in Central Illinois from early 2015 until his arrest in January 2018. He now appeals his sentence after pleading guilty to one count of possessing 50 grams or more of methamphetamin e with intent to distribute and one count of possessing fi rearms in furtherance of a drugtra ffi cking crime. Lee contends he should not have received2 No. 19-1300

two extra criminal history points under U.S.S.G. § 4A1.1(d) for dealing methamphetamine while on supervision for a drunk driving o ff ense. He also challenges the district judge’s imposition of a fi ne and a term of superv ised release that will prohibit him from interacting wi th known felons unless he receives the probation o ffi cer’s permission. Because this supervision term commits an imperm issible delegation of ArticleIII power relating to Lee’s liberty interest in familial association, we vacate the condition and remand for reassessment. We a ffi rm on all other grounds. I. Background In late 2017 and early 2018, DE A agents and Illinois State Police learned through multiple independent informants that Shawn Lee had been distributing large quantities of ice methamphetamine near Carlinville, Illinois. DEA agents con fi rmed those reports by arranging a controlled buy between a con fi

dential source and Lee on January 16, 2018, during which the source purchased over 83 grams of ice methamphetamine for $1,500. On January 23, 2018, state troopers conducted a planned tra ffi c stop on a vehicle drivenby Lee. Lee consented to a K-9 walkaround of the vehicle and the dog alerted to the presence of drugs. Troopers searched the car and found over seven pounds of ice methamphetamine and $19,170 in cash,including $900 of marked money used in the January 16 controlled buy. Agents arrested and interviewed Lee. He told them he had been dealing ice methamphetamine in the Carlinville area forthe last three years—since around January 2015—and admitted he intended to ship the se ized currency to his supplier in partial satisfaction of a drug debt. Lee started out transacting in eight-ounce quantities of methamphetamine but graduatedNo. 19-1300 3

to dealing pounds of drugs from about June 2017 until his arrest. During that seven-month period alone, Lee distributed approximately 100 pounds (45.36 kilograms) of methamphetamine. He purchased the drugs for $7,000 per pound (totaling $700,000 worth of methamphetamine) and resold them at $11,200 per pound ($1.12 million in sales). Investigators lacked enough information to determine the amount of drugs Lee dealt from the start of his illegal conduct until June 2017. Lee informed agents he turned to selling methamphetamine after losing his job because of his own drug use. Based on additional details gained during the investigation, agents obtained and executed a search warrant at Lee’s residence. Inside, agents discovered ice methamphetamine and various other suspected narcotics hidden throughout the house. Agents also discovered twelve fi rearms 1 in close proximity to the drugs, along with scales, drug paraphernalia, and assorted ammunition and magazines. The government ch arged Lee with one count of distributing 50 grams or more of methamphetamine for the January 16 controlled buy (Count 1), two counts of possessing 50 grams or more of methamphetamine with intent to distribute (Counts 2 and 3), and one count of possessing fi rearms in furtherance of a drug-tra ffi cking crime (Count 4). Lee entered a blind guilty plea on Counts 2 and 4. As set forth in the presentence report (“PSR”), the massive amount of drugs prompted a base o ff ense level of 38 for Count 2. The base level was then reduced for acceptance of responsibility,

1 Agents discovered a thirteenth gun—an antique that did not meet the technical “firearm” definition. Th e government did not charge Lee’s possession of that gun.4 No. 19-1300

resulting in a total o ff ense level of 35. Lee’s record earned him three criminal history points: one point for a 2015 drunk driving conviction and two points for commi tt ing the instant crimes while on supervision for the drunk driving o ff ense. The three total points placed L ee in criminal history category II, which, combined with the total o ff ense level of 35, resulted in a sentencing range of 188 to 235 months’ imprisonment on Count 2. The Guidelines range for Count 4 equaled the statutory minimum: 60 months’ imprisonment.

The PSR also included information about Lee’s fi nances, including a list of assets (totaling nearly $190,000) and a net worth greater than $102,000. 2 Despite this information, the probation o ffi cer opined, “it appears [Lee] does not have the ability to pay a fi ne or community restitution.” (PSR ¶ 96.) The Guidelines called for a fi ne range of $40,000 to $10,000,000. At sentencing, the district ju dge adopted the PSR’s factual fi ndings as her own. She calculated the same Guidelinesranges as set forth in the PSR: 188 to 235 months’ imprisonment on Count 2 and 60 months’ imprisonment on Count 4. Neither party objected. The district judge sentenced Lee to 210 months’ imprisonment, consisting of 150 months on Count 2—a below-Guidelines sentence—and 60 months on Count 4, to be served consecutively. The ju dge further imposed a $20,000 fi ne—a below-Guidelines amount —after weighing the huge amount of ice methamphetamin e Lee sold, the dangerousness of that drug, and the need to deprive o ff enders of ill-go tt en

2 We note Lee’s primary asset, his home, is in foreclosure, meaning his total assets and net worth will be su bstantially less upon his release from prison.No. 19-1300 5

gains against Lee’s available assets. Upon release, the judge ordered Lee to a term of fi ve years’ supervision. Among the several terms Lee must comply with during that period is Condition No. 7, which limits his ability to interact with known felons unless granted permission by the probation

o ffi cer. Two of Lee’s sons are convicted felons.

II. Discussion Lee challenges his criminal history score, the $20,000 fi ne, and supervisory Condition No. 7. We a ffi rm his sentence with one narrow exception. First, the district judge calculated Lee’s criminal history score correctly when she assessed two extra points under U.S.S.G. § 4A1.1(d). Second, the judge provided adequate consideration of the necessary factors to support the fi ne. And fi nally, Condition No. 7 implicates Lee’s familial association interests on a prospective level only, so, at this point, we need not wade into his constitutional argument’s merits. The same term of supervision, however, improperly delegates Article III power to the probation o ffi cer, requiring reassessment.

A. Lee’s Criminal History Lee maintains his criminal history score should not have been enhanced by U.S.S.G. § 4A1.1(d), which adds two points “if the defendant commi tt ed the instant o ff ense while under any criminal justice sentence, in cluding probation, parole, supervised release, imprisonment, work release, or escape status.” This challenge lacks merit because Lee engaged in6 No. 19-1300

conduct related to his o ff ense while on supervision for his state drunk driving conviction. 3 The commentary to § 4A1.1(d) instructs courts to add two points if the defendant commi tt ed the instant o ff ense, including any relevant conduct, while on supervision. U.S.S.G.§ 4A1.1(d), Application Note 4. When investigators interviewed Lee in January 2018, he admi tt ed to dealing methamphetamine in the region for th e previous three years. This course of dealing constitutes relevant conduct. See, e.g. , United States v. Stephenson , 557 F.3d 449, 456–57 (7th Cir. 2009) (holding defendant’s continuous deal ing of the same drug in the same locale using the same f ew distributors during the common eight-year time frame quali fi ed as conduct related to the charged transaction). His July 2015 drunk driving conviction and resulting year of supervision fall squarely within this time period. The district judge therefore awarded two extra criminal history points correctly under § 4A1.1(d). Lee’s only response to the relevant conduct hurdle is that his statements to investigators cannot be used to enhance his sentence (by way of his criminal history calculation). This argument misses the mark. Lee invokes language extractedfrom the safety-valve provision at 18 U.S.C. § 3553(f): “Information disclosed by a defendant under this subsection may not be used to enhance the sentence of the defendant unless the information relates to a violent o ff ense.” That provision does not apply here. The district court made no fi nding regarding the safety valve (the record does not indicate the safety valve ever came up at a ll), and in any event, Lee would

3 The parties debate whether Lee waived this challenge, but we do not address waiver here.No. 19-1300 7

not be eligible to receive its bene fi ts because he fails the following criteria: the defendant must not have “possess[ed] a fi rearm or other dangerous weapon ... in connection with the

o ff ense.” § 3553(f)(2); United States v. Collins , 924 F.3d 436, 440–41 (7th Cir. 2019). He possessed twelve fi rearms too many in connection with his drug business.

B. Lee’s $20,000 FineLee claims the district judge failed to justify his belowGuidelines fi ne, which the judge imposed over the probation

o ffi cer’s recommendation that Lee did not appear able to pay one. “When a district court determines that a fi ne is in order, we will only reverse its factual fi nding if it is clearly erroneous.” United States v. Artley, 489 F.3d 813, 826 (7th Cir. 2007). In other words, the record mustclearly indicate whether the district judge “properly has considered the relevant factors” set forth below. United States v. Bauer, 129 F.3d 962, 968 (7th Cir. 1997).

Section 5E1.2 of the Guidelines mandates the imposition of a fi ne unless “the defendant establishes that he is unable to pay and is not likely to become able to pay any fi ne.” U.S.S.G. § 5E1.2(a). “This language is to be taken seriously: the judge must impose a fi ne, unless the defendant demonstrates that he cannot pay anything, either at sentencing or in the foreseeable future.” United States v. Gomez , 24 F.3d 924, 926–27 (7th Cir. 1994). The defendant’s burden here is a heavy one “because almost everyone has or will acquire some assets.” Id. at 927. The Guidelines state the district judge “shall consider” eight factors before imposing a fi ne: (1) the need for the combined sentence to re fl ect the seriousness of the o ff ense (including the8 No. 19-1300

harm or loss to the victim and the gain to the defendant), to promote respect for the law, to provide just punishment and to a ff ord adequate deterrence; (2) any evidence presented as to the defendant’s ability to pay the fi ne (including the ability to pay over a period of time) in light of his earning capacity and fi nancial resources; (3) the burden that the fi ne places on the defendant and his dependents relative to alternative punishments;(4) any restitution or reparation that the defendant has made or is obligated to make;(5) any collateral consequences of conviction, including civil obligations arising from the defendant’s conduct; (6) whether the defendant previously has been fi ned for a similar o ff ense; (7) the expected costs to the government of any term of probation, or term of imprisonment and term of supervised release imposed; and (8) any other pertinent equitable considerations. U.S.S.G. § 5E1.2(d). Similar “factors to be considered” can be found at 18 U.S.C. § 3572(a). 4 When imposing a fi ne, a district judge need not make express or speci fi c fi ndings regarding each of the relevant

4 In addition to its own factors, § 3572(a) requires consideration of those listed under 18 U.S.C. § 3553(a).No. 19-1300 9

factors, Bauer, 129 F.3d at 966, although an express fi nding may nonetheless be made by adopting the PSR’s facts, id. (citing United States v. Monem , 104 F.3d 905, 912 (7th Cir. 1997)). This approach keeps the focus on the need for the judge to weigh the necessary factors without requiring her to give an “often unnecessary” articulation of her fi ndings. Id. at 967–68; see also United States v. Pe tty, 132 F.3d 373, 382 (7th Cir. 1997) (reciting Bauer ’s standard and explaining, “We desired to relieve the district courts, when possible, from the substantial burden of making express fi ndings when simply adopting the PSR will do as well.”).

The record reveals the districtjudge considered the relevant factors su ffi ciently. Before imposing Lee’s fi ne, the judge emphasized the seriousness of Lee’s o ff ense, which created “a signi fi cant danger to the communi ty”: Lee distributed a “massive amount” of ice methamphetamine—a “very dangerous” drug—and possessed a dozen fi rearms in connection with that o ff ense. (Lee’s Br. App. at 66.) See U.S.S.G. § 5E1.2(d)(1), and 18 U.S.C. § 3553(a)(1–2) (the sentencing court shall consider the nature, circumstances, and seriousness of the offense). She also underscored the need to deprive Lee of his illgo tt en gains and to deter others from a tt empting to pro fi t through similar illicit enterprises, see 18 U.S.C. §§ 3572(a)(5), 3553(a)(2)(B), by rejecting his sentencing argument that he used drug proceeds to help others. As the district judge stated, “So did El Chapo. He helped out his community as well with the ill-go tt en gains that he received from illegal drugs.” (Lee’s Br. App. at 67.) Put di ff erently, good deeds do not excuse the illegal acts that make them possible, nor do they outweigh the danger and harm Lee’s drug trade posed to the public.10 No. 19-1300

The PSR also contained information about other relevant factors, such as Lee’s fi nancial resources and the lack of dependents, pecuniary loss, and restitution. See U.S.S.G. § 5E1.2(d)(2–4); 18 U.S.C. § 3572(a)(1–3); see also United States v. Pa tt erson , 698 F. App’x 840, 841 (7th Cir. 2017) (a ffi rming the district judge’s justi fi cation for the imposed fi ne where he adopted the PSR’s factual fi ndings regarding these sameitems). Notably, the PSR detailed several assets with a combined value exceeding the ultimate fi ne amount, including Lee’s two automobiles and two all-terrain vehicles ($7,300 total), his work tools ($15,000), and $14,200 5 in savings bonds. (PSR ¶ 94.) By adopting the PSR’s contents, the district judge made express fi ndings for each of these factors, further supporting the imposed fi ne. Bauer, 129 F.3d at 966 (citing Monem , 104 F.3d at 912). Because the district judge accepted the PSR’s factual fi ndings yet departed from the probation o ffi cer’s estimate regarding Lee’s ability to pay a fi ne, Lee insists the fi ne be vacated under Bauer . In that case, we held the underpinnings of

a fi ne may be lacking when, for ex ample, “the district court adopts the factual fi ndings contained in the presentence report but deviates from the fi ne recommendation, if any, made

5 The PSR listed the savings bonds’ value erroneously as $20,000. Leefiled a post-sentencing motion under Fed. R. Crim. P. 35(a) seeking a reduced fine equal to the bonds’ actual worth ($14,200). The district judgedenied Lee’s request and reiterated the bases for the fine in a written order. (Doc. 39.) Both the Rule 35(a) motion and the resulting order were entered afterLee filed his notice of appeal, however, so the parties debatewhether we have jurisdiction to consider the order’s contents when addressing Lee’s fine challenge. We need not consider the order; it cites only Lee’s assets and the nature, circumstan ces, and severity of his crimes. The record already reflects a consideration of these factors.No. 19-1300 11

by the United States Probation O ffi ce, or alternatively, if the district court declines to adopt the fi ndings in the presentence report and makes no fi ndings of its own.” 129 F.3d at 968.

But Bauer ’s language describes situations in which the district court either imposes a fi ne inconsistent with its stated intentions or fails to make any fi ndings of fact at all. Id. at 967. We pointed to Monem as illustrative of the former, where the probation o ffi cer recommended a below -Guidelines fi ne because of the defendant’s fi nancial status. Bauer, 129 F.3d at 967 (discussing Monem , 104 F.3d at 911–12). But at Monem’s sentencing, the judge stated: “The Court will accept the recommendation of the presentence report and impose a fi ne of $15,000, which is the minimum fi ne.” Monem , 104 F.3d at 912 (emphasis added). So, the judge imposed a fi ne higher than the PSR’s recommendation while purporting to accept it. Wetherefore could not “accept the district court’s blanket statement that it accepted the re commendation of the PSR when an unexplained contradiction [was] evident from the record.” Id. The same ambiguity does not exist here. True, the district judge adopted the factual fi ndings of the PSR as her own near the start of Lee’s sentencing. But the record does not end on that rote announcement. Rath er, the judge entertained argument from the parties regarding Lee’s fi nancial status, rejected the probation o ffi cer’s recommendation of no fi ne, and in doing so reached her own conclusion that Lee could pay a $20,000 fi ne. And by adopting the PSR’s fi ndings regarding Lee’s total assets worth well in excess of that amount, the judge supported this conclusion su ffi ciently. Lee’s fi ne did not result from any error, clear or otherwise.12 No. 19-1300

C. Supervised Release Condition No. 7 The district judge also sentenced Lee to fi ve years’ supervised release on each count of conviction, to be served concurrently. Among the various terms of supervision, the judge ordered Lee not to:knowingly meet, communicate, or otherwise interact with any person wh om he knows to be a convicted felon or to be engaged in, or planning to engage in, criminal activity, unless granted permission to do so by the probation o ffi cer. (Lee’s Br. App. at 78.) Lee’s cha llenge to this condition is twofold, and both prongs stem from the fact that two of his sons— Ethan and Charles—are felons th emselves. First, Lee argues the condition commits an improper delegation of Article III power because it allows the probation o ffi cer—instead of the district judge—to determine whether Lee can enjoy the company of his own children. Second, Lee contends the condition will unjusti fi ably deprive him of the constitutional right of familial association.

1. Article III Delegation “Article III judges lack constitu tional authority to delegatethe duty of imposing a defendant’s punishment to a nonArticle III judge, such as a probation o ffi cer or treatment provider.” United States v. Wagner, 872 F.3d 535, 543 (7th Cir. 2017). At the outset, the government claims Lee did not preserve his delegation argument for appeal. We disagree. In his sentencing memorandum, Lee requested Condition No. 7 not be imposed, or, in the alternative, “that he be allowed to visit with his family without prior approval from the probation

o ffi ce .” (Doc. 30 at 8, emphasis added.) He reiterated thisNo. 19-1300 13

objection at sentencing. By contesting the need to receive prior approval from the probation o ffi cer, Lee’s objection went to the heart of the non-delegation rule, even if not so articulated. See United States v. Billups , 536 F.3d 574, 578 (7th Cir. 2008) (An objection may be su ffi cient to preserve an appellate argument even if the objector “o ff ers a new twist on that argument based upon additional authorit y on appeal.”). We therefore review Lee’s delegation claim de novo

. United States v. Schrode
, 839 F.3d 545, 554 (7th Cir. 2016). To determine whether a condition of supervised release violates the non-delegation rule, “we distinguish between permissible conditions that merely task the probation o ffi cer with performing ministerial acts or support services related to the punishment imposed and impermissible delegations that allow the o ffi cer to decide the nature or extent of the defendant’s punishment.” Wagner, 872 F.3d at 543 (internal quotation marks and citations omi tt ed). An example of a permissible, ministerial delegation would be “a condition requiring a defendant to a tt end treatment as approved by the probation

o ffi cer” because “the court itself ordered participation in the program and only provides the probation o ffi cer authority to manage the details and supervision of the program.” Id

. Here, the district court delegated the decision of whether Lee can associate with his two sons to the probation o ffi cer. The probation o ffi cer’s future task, then, is not merely to manage or supervise, but to determine whether, when, and how Lee can exercise his constitution al liberty interest in familial association. We think that is much more than a “ministerial act.” In this context, the clause “unless granted permission to do so by the probation o ffi cer” is overbroad and violates the non-delegation principle. Thus, it must be stricken from14 No. 19-1300

Condition No. 7—only the district judge can permit or deny Lee’s association with his sons. See Wagner , 872 F.3d at 543 (holding supervised release te rm improperly delegated district court’s Article III authority to determine the nature of defendant’s punishment where language left imposition of sex

o ff ender treatment up to probation o ffi cer); see also United States v. Voelker, 489 F.3d 139, 153–54 (3d Cir. 2007) (vacating condition that prohibited defendant from associating with minors absent the probation o ffi cer’s prior approval because it delegated “the sole authority for deciding if Voelker will ever have unsupervised contact with any minor, including his own children, for the rest of his life.”). We recognize that the probation o ffi cer is an authority on a supervisee’s record of compliance. With that knowledge comes the ability to identify associations and se tt ings that jeopardize a supervisee’s progress. But the same expertise does not supply unlimited Article III power to bar Lee from interacting with his children. Still, our decision today does not remove the probation o ffi cer’s insight from the equation. IfLee requests to communicate with Ethan and Charles following his release, the district ju dge may (and should) invite the probation o ffi cer to present the necessary evidence and make a recommendation. With the o ffi cer’s input in hand, the judge “can properly exercise [her] authority to determine whether such punishment is necessary to serve the principles and goals of supervised release.” Wagner, 872 F.3d at 543. For these reasons, we vacate Condition No. 7 and remand for the district court to revise its language in a way that keeps the authority to permit familial association with the judge. Weemphasize that our holding is limited to the extent Lee’s delegation challenge relates to this fundamental liberty interest.No. 19-1300 15

Indeed, his argument on appeal rests on this narrow ground only. But more to the point, the magni fi ed nature of Lee’s familial interest, as we highlight below, sets this case apart fromthose that require no more than routine review by the probation o ffi cer. See United States v. Armour, 804 F.3d 859, 870 n.3 (7th Cir. 2015) (Le tt ing the probation o ffi cer decide whether

an o ff ender may associate with his children while on supervised release is more serious th an delegating authority to permit a defendant’s interaction wi th any ordinary felon.). Our holding does not reach run-of-the-mill probationer requests
to a tt end barbecues, church services, or other benign community gatherings where known fe lons might be encountered. Those determinations remain appropriately with the probation o ffi cer. This is an exceptional case.

2. Constitutional ChallengeWe are sympathetic to Lee’s second concern, and it is a serious one. The liberty interest he raises—a parent’s right toenjoy the companionship of his children—“is perhaps the oldest of the fundamental liberty interests recognized by [the Supreme Court].” Troxel v. Granville , 530 U.S. 57, 65 (2000). 6 And in no way do we diminish Lee’s liberty interest by

6 Ethan and Charles, however, ar e not minors—they were both 23 years old as of November 2018. (PSR¶ 65.) Query whether their age detracts from Lee’s claimed liberty interest. See Russ v. Watts , 414 F.3d 783, 788 (7th Cir. 2005) (Observing several circuits have been “reluctant to extend the constitutional protections afforded the parent-child relationship to cases involving adult children.”). While we declined in Russ to “impose an absolute rule that parents of adult children lack any liberty interest intheir relationship with their children,” we nonetheless stated, “minor children’s need for the guidance and support of their parents warrants sharply different constitutional treatment.” Id. at 790 (internal quotation marks and citations omitted).16 No. 19-1300

commenting that his situation is both rare and unfortunate when it comes to family relati onships. According to the PSR,Ethan is serving three concurrent sentences in Illinois for possession of methamphetamine. Hi s expected release date is November 2021. Charles is serving an eighteen-year sentence in Illinois for aggravated delivery of methamphetamine. His projected release date is March 2026. (PSR ¶ 65.) Fortunately for Lee, he enjoys a good relationship with his youngest son, Zander, who has maintained regular contact with and visited Lee in prison. We hope Ethan and Charles will do the same once their prison terms end, al though that could depend in part on their own conditions of supervision. Still, whereas the improper delegation has already been commi tt ed by the district court’s fi nal judgment, Lee’s concern about a constitutional infr ingement is too prospective for us to address at this juncture. Lee received a sentence of 210 months’ imprisonment (seventeen and a half years) and his terms of supervision will not take e ff ect until his release. See United States v. Kappes , 782 F.3d 828, 859 (7th Cir. 2015) (holding claimed violation of right to familial association imposed by supervision terms not yet ri pe in light of twenty-year sentence). A lot can happen during that time. See id. at 838 (recommending district judges reassess defendants’ conditions of supervision on the eve of release from prison; “A defendant may change substantially during a long prison sentence, and the world outside the prison wa lls may change even more.”); United States v. Siegel , 753 F.3d 705, 708 (7th Cir. 2014) (“Conditions that may seem sensible at sentencing may not be sensible many years later, when the defendant is fi nally releasedfrom prison.”). For example, Lee might rehabilitate his serious drug addiction (detailed at length in the PSR) through the Bureau of Prison’s substanc e abuse programs such thatNo. 19-1300 17

associating with felons—especially those who are involved in drugs, like Lee’s sons—no longer presents a risk of recidivism or relapse. As the PSR explains, Lee interacted with criminals as part of his o ff ense conduct, but he only turned to dealing methamphetamine in the fi rst place after losing his job because of his own drug use. (PSR ¶¶ 23, 118.) Moreover, the condition Lee challenges might never threaten his liberty interest at all if the district judge grants Lee permission to interact with Ethan and Charles. By its own language, Condition No. 7 does not completely bar Lee from associating with his sons; the judge “may allow contact ... if [she] deems it appropriate; the condition is not a blanket ban.” See United States v. Llantada , 815 F.3d 679, 685 (10th Cir. 2016) (rejecting defendant’s associational rights challenge to nearly identical supervised release condition). Lee has provided no reason to believe that, with the probation o ffi cer’s recommendation in hand, the judge will refuse permission to communicate or associate with Ethan and Charles. And we assume the probation o ffi cer will address requests to associate and make recommendations in a reasonable manner. Kappes , 782 F.3d at 857–58. At sentencing, the probation o ffi cer explained his department reviews requests to associate simply for whether the desired interaction will “generat e any additional risk for noncompliance” with the conditions of supervised release. (Lee’s Br. App. at 9.) Speaking hy pothetically, the probation o ffi cer noted his o ffi ce would grant (now, recommend granting) permission for Lee to contact Etha n and Charles if the two sons abide by their own terms of probation and supervision.

The record re fl ects a preference for allowing contact between Lee and his sons provided all parties are progressing in their respective rehabilit ative sentences. Receiving18 No. 19-1300

permission to associate, therefore, is largely up to all three

men. See United States v. Edwards , 944 F.3d 631, 637 (7th Cir. 2019) (rejecting defendant’s va gueness challenge to a condition that prohibited unauthorized contact with minors because defendant gave “no reason to believe that the probation

o ffi cer would refuse” permission to spend time with his minor nephew). By declining to review Lee’s constitutional challenge at this time, we do not mean a defendant can never immediately appeal a condition of supervis ed release following entry ofjudgment. We have reviewed many such challenges, including where the terms of supervision required the defendant to submit to drug testing or to participate in sex o ff ender treatment, or prohibited the defendant from associating with white supremacy groups or from using the internet entirely. See United States v. Rhodes , 552 F.3d 624, 629 (7th Cir. 2009) (collecting cases). But the cond itions in those cases were de fi

nite, unlike here. The district judge must fi rst deny a request to contact Lee’s sons for any lib erty interest to be implicated, and such a denial would likely fl ow only from Lee’s or his sons’ hypothetical noncompliance with their respective terms of supervision. If the judge prohibits contact between Lee and his sons down the line, Lee may bring a challenge then to assert his constitutional rights, Llantada , 815 F.3d at 685, and he can seek to modify his supervised release terms at any time before his supervision ends. See 18 U.S.C. § 3583(e)(2); United States v. St. Clair, 926 F.3d 386, 389 (7th Cir. 2019). Our approach here promotes e ffi ciency over “perpetuating expensive and time-consuming appeals and resentencings ... .” United States v. Silvious , 512 F.3d 364, 371 (7th Cir. 2008).No. 19-1300 19

III. Conclusion For all these reasons, Condition No. 7 is VACATED and REMANDED to the district co urt for reconsideration consistent with this opinion. Lee’s sentence is otherwise AFFIRMED.20 No. 19-1300

S T

. E VE , Circuit Judge , concurring in part. I agree with my colleagues that the district co urt correctly calculated Shawn Lee’s criminal history score and that Lee’s fi ne did not resultfrom any error. I further agree that Supervised Release Condition No. 7 raises an issue of improper delegation of Article III power to a probation o ffi cer because of Lee’s underlying constitutionally protected liberty interest in associating withhis children. I disagree, however, that Lee’s challenge to Condition No. 7 is prospective such that it precludes our review of Lee’s constitutional argument. A condition of supervised release is unripe for purposes of our review only if it is “subje ct to a string of contingencies.” United States v. Wagner, 872 F.3d 535, 542 n.2 (7th Cir. 2017) (rejecting an argument that a condition of supervised releaseis not ripe for review). The condition that Lee challenges today does not rely on any contingencies: it sets as a default rule that Lee cannot speak with his tw o sons over his term of supervised release. See United States v. Johnson , 756 F.3d 532,539–40 (7th Cir. 2014) (concluding that a challenge to a condition of supervised release is ripe because “if we do nothing the default will be that the specia l condition is in place.”). The majority suggests that for this condition to impinge on Lee’s constitutionally protected liberty interest, Lee would have to request to communicate with his children, and the district court would have to deny that request. I respectfully disagreethat a challenge to a properly preserved condition of supervised release is premature because the court or a probation

o ffi cer would fi rst need to deny a request for an exception to the rule.Indeed, we have already resolved Lee’s constitutional argument: we determined that the delegation to probation ofNo. 19-1300 21

the administration of Condition No. 7 was impermissible because ofLee’s underlying constitutionally protected liberty interest in associating with his children. Slip Op. 13–15. We have said before that a condition of supervised release may infringe on a constitutionally protected right or interest, but the condition must be “reasonably related to the ends of rehabilitation and protection of the public from recidivism.” United States v. Armour, 804 F.3d 859, 870 (7th Cir. 2015) (quoting United States v. Sines , 303 F.3d 793, 801 (7th Cir. 2002)). A district court must “provide some rationale for why it believed [a challenged condition of supe rvised release] would be helpful” to these ends, rather than merely state that it is so. United States v. Canfield , 893 F.3d 491, 496 (7th Cir. 2018). We further have explained that courts must consider the infringement“more scrupulously” when it impacts deep, personal relationships. Sines , 303 F.3d at 801–02.Here, the district court did not discuss why a bar on communicating with his children would aid in Lee’s rehabilitationor prevent his recidivism, and instead dismissed Lee’s objection on the ground that probation would address it upon his release from custody. Given th e fundamental importance of the constitutionally protected liberty interest at stake—that Lee will risk returning to prison if he communicates with his own children while on supervised release—this explanation is woefully insufficient. Accord ingly, I would vacate the condition and remand to the districtcourt not only to remedy theimpermissible delegation, but also to carve out a limited exception to Condition No. 7 for Lee’s children, or to otherwise provide a sufficient rationale fo r their inclusion in the terms of the condition.