### 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

____________________

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 received two extra criminal history points under U.S.S.G. § 4A1.1(d)2 No. 19-1300

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 violates the rule against delegating Article III power, 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 graduated to dealing pounds of drugs from about June 2017 until his arrest. During that seven-month period alone, Lee distributedNo. 19-1300 3

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 charged Lee with one count of distributing 50 grams or more of methamphetamine for th e January 16 controlled buy(Count 1), two counts of possessing 50 grams or more of methamphetamine with intent to di stribute (Counts 2 and 3), and one count of possessing fi rearms in furtherance of a drug-traffi 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, 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

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

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 judge further imposed a $20,000 fi ne—a below-Guidelines amount—after we ighing the huge amount of ice methamphetamine Lee sold, the dangerousness of that drug, and the need to deprive o ff enders of ill-go tt en gains against Lee’s available assets. Upon release, the judge ordered Lee to a term of fi ve years’ supervision. Among the several

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

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 that arg ument’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 in conduct related to his o ff ense while on superv ision 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,

3 The parties debate whether Lee waived this challenge, but we do not address waiver here.6 No. 19-1300

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 the 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 dealing of the same drug in the same locale using the same few distributors during the common eight-year time frame quali fi ed as conduct related tothe 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 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.No. 19-1300 7

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 the 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 to8 No. 19-1300

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 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 th e 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

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

United States v. Pe tt y , 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.

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 he10 No. 19-1300

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 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

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

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.

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:12 No. 19-1300

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: fi rst, Lee maintains the condition, as wri tt en, commits animproper delegation of Article III power to the probation offi cer; and second, because two of his sons—Ethan and Charles—are felons themselves, Lee argues the condition will deprive him of the constitutional right of familial association.

1. Article III Delegation “Article III judges lack constitu tional authority to delegate the duty of imposing a defendan t’s punishment to a non-Article 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 re quested 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 this 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 thatargument based upon additional authority on appeal .”). We therefore review Lee’s delegation claim de novo

. United States v. Schrode , 839 F.3d 545, 554 (7th Cir. 2016).No. 19-1300 13

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

. But here, the district court delegated the decision ofwhether Lee could associate with felons to the probation offi cer. The probation o ffi cer’s future task, then, is not merely to manage or supervise, but to determine whether, when, and how a particular component of Lee’s punishment—Condition No. 7—is imposed. In that sense, Lee’s case mirrors Wagner
,where we remanded based on a supervisory condition’s language allowing a sex-o ff ender-treatment provider to determine whether the defendant could access pornography. 872 F.3d at 542–43. Lee’s case also aligns with United States v. Voelker, 489 F.3d 139 (3d Cir. 2007). The contested condition inthat case prohibited the defendant from associating with minors absent the probation o ffi cer’s prior approval. Id. at 153. The Third Circuit vacated the condition because it anointed the probation o ffi cer with “the sole auth ority for deciding if Voelker will ever have unsupervised contact with any minor, including his own children, for the rest of his life.” Id. at 154.14 No. 19-1300

The condition here is no di ff erent. Our colleague’s separate opinion submits the probation o ffi cer cannot determine whether a condition should go into e ff ect but can nevertheless “manage,” i.e., allow, exceptions to the condition. We fail to see the functional di ff erence. Article III does not confer upon the probation o ffi cer the authority to release a convict from a component of his or her sentence, either. The clause “unless granted permission to do so by the probation o ffi cer” violates this principle and must be stricken from Condition No. 7— only the district judge can permit or deny association. Wagner
, 872 F.3d at 543. We agree with our colleague that the probation o ffi cer is an authority on a supervisee’s re cord of compliance. With thatknowledge comes the ability to identify associations and settings that jeopardize a supervisee ’s progress. But the same expertise does not supply Article III power. Still, our decision today does not remove the probation o ffi cer’s insight from the equation. If Lee requests to communicate with Ethan and Charles following his release, the district judge 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 prop erly exercise [her] authority to determine whether such punishment is necessary to serve the principles and goals of supervised release.” Id. We vacate and remand this condition for reassessment. 6

6 We understand district judges impose associational restrictions like the one here routinely, often allowing defendants to seek exceptions from their probation officers. And we recognize our holding today conflicts with our rejection of a similar delegation challenge in United States v. Armour , 804 F.3d 859, 870 n.3 (7th Cir. 2015), which the government cites. But we decided Armour without the benefit of our later analysis in SchrodeNo. 19-1300 15

2. Familial AssociationWe 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). 7 Andin no way do we diminish Lee’s liberty interest by commenting that his situation is both rare and unfortunate when it comes to family relationships. According to the PSR, Ethan is serving three concurrent sentence s in Illinois for possession of methamphetamine. His expected release date is November 2021. Charles is serving an eight een-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

(2016) and Wagner(2017). These two subsequent opinions make clear that decisions of whetherto enforce certain components of a sentence cannot be delegated to the probation officer. Pr obation officers cannot grant permission to associate when a condition of supervised release bars association otherwise. Only Article III ju dges can make that call.

7 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

prison. We hope Ethan and Charles will do the same once their prison terms end, although that could depend in part on their own conditions of supervision. Still, Lee’s concern is too prospective for us to address atthis 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 asso ciation imposed by supervision terms not yet ripe 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 theeve of release from prison; “A defendant may change substantially during a long prison se ntence, and the world outside the prison walls 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 released from prison.”). For example, Lee might rehabilitate his serious drug addiction (detailed at length in the PSR) through the Bureau of Prison’s substance abuse programs such that associating with felons— especially those who are involved in drugs, like Lee’s sons— no longer presents a risk of re cidivism 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 fromNo. 19-1300 17

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 progressingin their respective rehabilitative sentences. Receiving 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 vagueness ch allenge to a condition thatprohibited 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 of18 No. 19-1300

judgment. 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).

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.No. 19-1300 19

S T

. E VE , Circuit Judge , dissenting in part and concurring in part. I agree with my colleague s that the district court correctly calculated Shawn Lee’s criminal history score and that Lee’s fi ne did not result from any error. I disagree, however, that Lee’s challenge to Condition No. 7 is prospective suchthat it precludes our review of Lee’s argument that the condition infringes on his constitution ally protected interest in associating with his children. An d while I agree with my colleagues that Supervised Releas e Condition No. 7 raises an issue of improper delegation of Article III power to a probation

o ffi cer, in my view this is only be cause of this underlying constitutionally protected liberty inte rest. Therefore, while I also vote to vacate this condition an d remand to the district court, I would do so only on the limit ed issue of carving out an exception to Supervised Release Condition No. 7 or providing a

su ffi cient explanation for it. I wr ite separately as to SectionII.C to explain my views on the questions of ripeness and delegation. First, although we have previously held that in some cases certain conditions are “too contin gent to be ripe for review” at the time of appeal, United States v. Kappes , 782 F.3d 828, 859 (7th Cir. 2015), I do not believe th is is such a case. The majority cites United States v. Rhodes , 552 F.3d 624 (7th Cir. 2009), as an example where we found a challenge to a supervised release condition unripe. In Rhodes , the defendant contested a condition that he “undergo a psychosexual evaluation and participate in an outpatient sex o ff ender counseling program if recommended by the evaluator which may involve use of polygraph and plethysmograph examinations.” Id. at 626. Rhodes objected to the examinations on general Fifth Amendment grounds. Id. This condition, though, required a number of events to bear out before there was any possible20 No. 19-1300

encroachment on Rhodes’s Fifth Amendment rights, namely(1) an evaluator had to recommend participation in a counseling program and (2) if that occu rred, the examinations had to be utilized. We therefore held that Rhodes’s objection to the examination was premature—Rhodes “may only be a ff ected by the condition after a string of contingencies.” Id. at 629. And in Kappes —another decision the majority cites—when adefendant challenged a condition banning him from communicating with all minors because he or an extended family member might have a minor child at the time of his release—we declined to direct the district court to modify the condition. Kappes , 782 F.3d at 859. This condition was “too contingent,” we held, because the defendant did not yet have any children and received a sentence of 20 years’ imprisonment at age 47, making it less likely he would have children after his release. Id. The same contingencies are no t at play in the conditionLee challenges today. The disputed condition will set as a default rule that Lee cannot speak with his two sons over his term of supervised release—in this case, a term of fi ve years. Unlike the conditions challenged in Rhodes and in Kappes
, nothing must fi rst occur before that condition goes into e ff ect: as soon as his supervised re lease begins, he may not speak with his (currently existing) children. The majority suggests that for this condition to impi nge on Lee’s constitutionallyprotected liberty interest, Lee would have to request to communicate with his children, and the district court would have to deny that request. I respec tfully disagree that a challenge to a properly preserved condition of supervised release is premature because the co urt or a probation o ffi cer would fi rst need to deny a request for an exception to the rule.No. 19-1300 21

Because I do not view Lee’s challenge as prospective, Iwould resolve it on the merits. While we review “the imposition of an objected-to condition of supervised release for abuse of discretion,” “[t]he cons titutionality of a condition of release is a legal determin ation we review de novo.” United States v. Shannon , 851 F.3d 740, 743 (7th Cir. 2017). We further review whether the district cour t adequately explained a chosen condition of supervised release de novo. Id.As the majority notes, Lee correctly identifies that Condition No. 7 infringes on his constitutionally protected liberty interest in associating with hi s children. “The Supreme Courthas long recognized as a component of substantive due process the right to familial relations.” Brokaw v. Mercer Cty. , 235 F.3d 1000, 1018 (7th Cir. 2000) (citing Prince v. Massachusetts
, 312 U.S. 158, 166 (1944); Meyer v. Nebraska , 262 U.S. 390, 399 (1923); Santosky v. Kramer, 455 U.S. 745, 753 (1982)). Indeed, “parents have a liberty interest, protected by the Constitution, in having a reasonable opportun ity to develop close relations with their children.” Hodgson v. Minnesota , 497 U.S. 417, 484 (1990) (Scalia, J., concurring in part and dissenting in part); see also Lassiter v. Dep’t of Soc. Servs. , 452 U.S. 18, 27 (1981) (“This Court’s decisions have by now made plain beyond the need for multiple citation that a pare nt’s desire for and right to the companionship, care, custody and management of his or her children is an important intere st.” (internal quotation marks and citation omitted)).

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 ofthe public from recidivism.” United States v. Armour, 804 F.3d 859, 870 (7th Cir. 2015)22 No. 19-1300

(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 supervised 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 scrupulou sly” 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 distri ct court to carve out a limitedexception to Condition No. 7 for Lee’s children, or to otherwise provide a sufficient rationa le for their inclusion in the terms of the condition.Second, the majority concludes that any condition allowing a probation officer to grant exceptions to a restriction prohibiting probationers from asso ciating with convicted felons runs afoul of the non-delegation doctrine. As the majority recognizes, this holding contradicts our conclusion in Armour
, where we rejected an argument that “giving the probation officer the power to determine whether Armour has permission to associate with convicted felo ns violates the non-delegation principle.” Armour
, 804 F.3d at 870 n. 3. Armour is binding law in this circuit.No. 19-1300 23

In subsequent cases, we have distinguished “between permissible conditions that ‘mere ly task the probation officer with performing ministerial acts or support services related to the punishment imposed’ and impermissible delegations ‘that allow the officer to decide the nature or extent of the defendant’s punishment.’” United States v. Wagner , 872 F.3d 535, 543 (7th Cir. 2017) (quoting United States v. Schrode , 839 F.3d545, 555 (7th Cir. 2016)). Probation officers frequently navigate the administration of conditions like the one Lee disputes here: they routinely and effectively manage requests from probationers about whether they can attend events like a church picnic or a neighbor’s graduation party, or whether they can visit any of the nume rous places where they might encounter convicted felons in their communities and beyond.This responsibility appropriately belongs in a probation officer’s domain: as the probatio ner’s supervisor, the probationofficer is aware of his compliance with conditions and progress during his period of release. Only because of the magnitude of the liberty interest at stake in this case do I believe this condition is more analogous to determining the “nature or extent” of the punishment. Indeed, Lee himself only challenges the delegation on this narrow ground. Our opinions in Schrode and Wagner do not suggest otherwise. In Schrode , we determined that the defendant waived hisnondelegation challenge by failing to raise it before the district court. Schrode , 839 F.3d at 555–56. Although we did not reach the issue, we said in dict a that “a condition of sex offender treatment ‘as deemed necessary by probation,’” troubled us because it delegated to a probation officer “the underlying judgment of whether the condition will be imposed at24 No. 19-1300

all.” Id. at 556. And in Wagner
, 1 we struck down a condition that similarly allowed probatio n to determine “whether access to adult pornography shou ld...be restricted or denied.” Wagner, 872 F.3d at 543 (internal quotations omitted). These conditions are not analogous to the one presented here. Where those conditions allowed probation to determine whether they would go into effe ct in the first instance, thecondition here permits probation solely to manage exceptions. This is properly within probation’s “broad authority to manage and supervise probationers.” Schrode , 839 F.3d at 555. Therefore, while I would also re mand to the district court to strike “by the probation officer” from the text of Condition No. 7, I would limit the reach of our holding on this issue to continue to allow probation to make exceptions to conditions prohibiting interactions with known felons.

1 Notably, the supervised release condition at issue in Wagner also implicated a constitutionally protected liberty interest. There, the defendant objected to a condition allowing a treatment provider to determine whether he could view adult pornog raphy, which receives First Amendment protection. Wagner , 872 F.3d at 542 (citing United States v. Taylor, 796 F.3d 788, 793 (7th Cir. 2015)).