In the 

United States Court of Appeals 

For the Seventh Circuit ____________________ 

No. 19-1300 

UNITED STATES OF AMERICA, 

Plaintiff-Appellee, 

v.

SHAWN A. LEE, 

Defendant-Appellant. 

____________________ 

Appeal from the United States District Court for the 

Central District of Illinois. 

No. 3:18-cr-30011 — Sue E. Myerscough, Judge. 

____________________ 

ARGUED SEPTEMBER 26, 2019 — DECIDED FEBRUARY 18, 2020 —

AMENDED JUNE 9, 2020 

____________________ 

Before BAUER, MANION, and ST. EVE, Circuit Judges. 

MANION, 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 methamphetamine with intent to distribute 

and one count of possessing firearms in furtherance of a drugtrafficking crime. Lee contends he should not have received 
2 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 offense. He also challenges the district judge’s 

imposition of a fine and a term of supervised release that will 

prohibit him from interacting with known felons unless he receives the probation officer’s permission. Because this supervision term commits an impermissible delegation of Article 

III power relating to Lee’s liberty interest in familial association, we vacate the condition and remand for reassessment. 

We affirm on all other grounds. 

I. Background

In late 2017 and early 2018, DEA 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 confirmed 

those reports by arranging a controlled buy between a confidential 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 traffic stop on a vehicle driven by 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 for 

the last three years—since around January 2015—and admitted he intended to ship the seized currency to his supplier in 

partial satisfaction of a drug debt. Lee started out transacting 

in eight-ounce quantities of methamphetamine but graduated 
No. 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 

firearms1 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 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 

firearms in furtherance of a drug-trafficking 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 offense 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. The government did not charge Lee’s 

possession of that gun. 
4 No. 19-1300 

resulting in a total offense level of 35. Lee’s record earned him 

three criminal history points: one point for a 2015 drunk driving conviction and two points for committing the instant 

crimes while on supervision for the drunk driving offense. 

The three total points placed Lee in criminal history category 

II, which, combined with the total offense 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 finances, 

including a list of assets (totaling nearly $190,000) and a net 

worth greater than $102,000.2 Despite this information, the 

probation officer opined, “it appears [Lee] does not have the 

ability to pay a fine or community restitution.” (PSR ¶ 96.) The 

Guidelines called for a fine range of $40,000 to $10,000,000. 

At sentencing, the district judge adopted the PSR’s factual 

findings as her own. She calculated the same Guidelines 

ranges 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 

fine—a below-Guidelines amount—after weighing the huge 

amount of ice methamphetamine Lee sold, the dangerousness 

of that drug, and the need to deprive offenders of ill-gotten 

2 We note Lee’s primary asset, his home, is in foreclosure, meaning his 

total assets and net worth will be substantially 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 five 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 

officer. Two of Lee’s sons are convicted felons. 

II. Discussion

Lee challenges his criminal history score, the $20,000 fine, 

and supervisory Condition No. 7. We affirm 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 

fine. And finally, 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 officer, 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 committed the instant offense while under 

any criminal justice sentence, including probation, parole, supervised release, imprisonment, work release, or escape status.” This challenge lacks merit because Lee engaged in 
6 No. 19-1300 

conduct related to his offense 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 committed the instant offense, 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 admitted 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 qualified 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 extracted 

from 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 offense.” That provision 

does not apply here. The district court made no finding regarding the safety valve (the record does not indicate the 

safety valve ever came up at all), 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 benefits because he fails the following criteria: the defendant must not have “possess[ed] a 

firearm or other dangerous weapon ... in connection with the 

offense.” § 3553(f)(2); United States v. Collins, 924 F.3d 436, 

440–41 (7th Cir. 2019). He possessed twelve firearms too many 

in connection with his drug business. 

B. Lee’s $20,000 Fine 

Lee claims the district judge failed to justify his belowGuidelines fine, which the judge imposed over the probation 

officer’s recommendation that Lee did not appear able to pay 

one. “When a district court determines that a fine is in order, 

we will only reverse its factual finding if it is clearly erroneous.” United States v. Artley, 489 F.3d 813, 826 (7th Cir. 2007). 

In other words, the record must clearly 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 fine unless “the defendant establishes that he is unable to 

pay and is not likely to become able to pay any fine.” U.S.S.G. 

§ 5E1.2(a). “This language is to be taken seriously: the judge 

must impose a fine, 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 fine: 

(1) the need for the combined sentence to reflect 

the seriousness of the offense (including the 
8 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 afford adequate 

deterrence; 

(2) any evidence presented as to the defendant’s 

ability to pay the fine (including the ability to 

pay over a period of time) in light of his earning 

capacity and financial resources; 

(3) the burden that the fine 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 

fined for a similar offense; 

(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 fine, a district judge need not make express or specific findings 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 finding 

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 findings. Id. at 967–68; 

see also United States v. Petty, 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 findings when simply adopting the 

PSR will do as well.”). 

The record reveals the district judge considered the relevant factors sufficiently. Before imposing Lee’s fine, the judge 

emphasized the seriousness of Lee’s offense, which created “a 

significant danger to the community”: Lee distributed a “massive amount” of ice methamphetamine—a “very dangerous” 

drug—and possessed a dozen firearms in connection with 

that offense. (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 illgotten gains and to deter others from attempting to profit 

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-gotten gains that he received from illegal 

drugs.” (Lee’s Br. App. at 67.) Put differently, 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 financial 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. Patterson, 698 F. App’x 840, 841 (7th Cir. 2017) (affirming the 

district judge’s justification for the imposed fine where he 

adopted the PSR’s factual findings regarding these same 

items). Notably, the PSR detailed several assets with a combined value exceeding the ultimate fine amount, including 

Lee’s two automobiles and two all-terrain vehicles ($7,300 total), his work tools ($15,000), and $14,2005 in savings bonds. 

(PSR ¶ 94.) By adopting the PSR’s contents, the district judge 

made express findings for each of these factors, further supporting the imposed fine. Bauer, 129 F.3d at 966 (citing Monem, 

104 F.3d at 912). 

Because the district judge accepted the PSR’s factual findings yet departed from the probation officer’s estimate regarding Lee’s ability to pay a fine, Lee insists the fine be vacated under Bauer. In that case, we held the underpinnings of 

a fine may be lacking when, for example, “the district court 

adopts the factual findings contained in the presentence report but deviates from the fine recommendation, if any, made 

5 The PSR listed the savings bonds’ value erroneously as $20,000. Lee 

filed 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 judge 

denied 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 after Lee filed his notice of appeal, however, so the parties debate 

whether 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, circumstances, and severity of his crimes. The 

record already reflects a consideration of these factors. 
No. 19-1300 11

by the United States Probation Office, or alternatively, if the 

district court declines to adopt the findings in the presentence 

report and makes no findings of its own.” 129 F.3d at 968. 

But Bauer’s language describes situations in which the district court either imposes a fine inconsistent with its stated intentions or fails to make any findings of fact at all. Id. at 967. 

We pointed to Monem as illustrative of the former, where the 

probation officer recommended a below-Guidelines fine because of the defendant’s financial 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 fine of 

$15,000, which is the minimum fine.” Monem, 104 F.3d at 912 

(emphasis added). So, the judge imposed a fine higher than 

the PSR’s recommendation while purporting to accept it. We 

therefore could not “accept the district court’s blanket statement that it accepted the recommendation 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 findings of the PSR as her own near 

the start of Lee’s sentencing. But the record does not end on 

that rote announcement. Rather, the judge entertained argument from the parties regarding Lee’s financial status, rejected

the probation officer’s recommendation of no fine, and in doing so reached her own conclusion that Lee could pay a 

$20,000 fine. And by adopting the PSR’s findings regarding 

Lee’s total assets worth well in excess of that amount, the 

judge supported this conclusion sufficiently. Lee’s fine 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 five 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 whom 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 officer. 

(Lee’s Br. App. at 78.) Lee’s challenge to this condition is twofold, and both prongs stem from the fact that two of his sons—

Ethan and Charles—are felons themselves. First, Lee argues 

the condition commits an improper delegation of Article III 

power because it allows the probation officer—instead of the 

district judge—to determine whether Lee can enjoy the company of his own children. Second, Lee contends the condition 

will unjustifiably deprive him of the constitutional right of familial association. 

1. Article III Delegation 

“Article III judges lack constitutional authority to delegate 

the duty of imposing a defendant’s punishment to a nonArticle III judge, such as a probation officer 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 

office.” (Doc. 30 at 8, emphasis added.) He reiterated this 
No. 19-1300 13

objection at sentencing. By contesting the need to receive prior 

approval from the probation officer, 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 sufficient to preserve an appellate argument 

even if the objector “offers a new twist on that argument 

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). 

To determine whether a condition of supervised release 

violates the non-delegation rule, “we distinguish between 

permissible conditions that merely 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.” Wagner, 872 F.3d at 543 (internal quotation marks and citations omitted). An example of a permissible, ministerial delegation would be “a condition requiring 

a defendant to attend treatment as approved by the probation 

officer” because “the court itself ordered participation in the 

program and only provides the probation officer 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 officer. 

The probation officer’s future task, then, is not merely to manage or supervise, but to determine whether, when, and how 

Lee can exercise his constitutional 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 officer” is overbroad and violates the 

non-delegation principle. Thus, it must be stricken from 
14 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 term improperly delegated district court’s Article III authority to determine the nature of defendant’s punishment where language left imposition of sex 

offender treatment up to probation officer); 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 officer’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 officer is an authority on 

a supervisee’s record of compliance. With that knowledge 

comes the ability to identify associations and settings 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 officer’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 officer to present the necessary evidence and make 

a recommendation. With the officer’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. We 

emphasize 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 magnified nature of Lee’s familial interest, as we highlight below, sets this case apart from 

those that require no more than routine review by the probation officer. See United States v. Armour, 804 F.3d 859, 870 n.3 

(7th Cir. 2015) (Letting the probation officer decide whether 

an offender may associate with his children while on supervised release is more serious than delegating authority to permit a defendant’s interaction with any ordinary felon.). Our 

holding does not reach run-of-the-mill probationer requests 

to attend barbecues, church services, or other benign community gatherings where known felons might be encountered. 

Those determinations remain appropriately with the probation officer. This is an exceptional case. 

2. Constitutional Challenge 

We are sympathetic to Lee’s second concern, and it is a serious one. The liberty interest he raises—a parent’s right to 

enjoy 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, are 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 in 

their 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 relationships. According to the PSR, 

Ethan is serving three concurrent sentences in Illinois for possession of methamphetamine. His 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, although that could depend in 

part on their own conditions of supervision. 

Still, whereas the improper delegation has already been 

committed by the district court’s final judgment, Lee’s concern about a constitutional infringement 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 effect 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 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 the eve of release from prison; “A defendant 

may change substantially during a long prison sentence, 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 finally 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 
No. 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 offense conduct, but he only turned to dealing 

methamphetamine in the first 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 officer’s recommendation in hand, the judge will refuse permission to communicate or associate with Ethan and Charles. And we assume the 

probation officer will address requests to associate and make 

recommendations in a reasonable manner. Kappes, 782 F.3d at 

857–58. At sentencing, the probation officer explained his department reviews requests to associate simply for whether the 

desired interaction will “generate any additional risk for noncompliance” with the conditions of supervised release. (Lee’s 

Br. App. at 9.) Speaking hypothetically, the probation officer 

noted his office would grant (now, recommend granting) permission for Lee to contact Ethan and Charles if the two sons 

abide by their own terms of probation and supervision. 

The record reflects a preference for allowing contact between Lee and his sons provided all parties are progressing 

in their respective rehabilitative sentences. Receiving 
18 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 vagueness challenge to a condition that prohibited unauthorized contact with minors because defendant gave “no reason to believe that the probation 

officer 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 supervised release following entry of 

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 offender 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 conditions in those cases were definite, unlike here. The district judge must first deny a request 

to contact Lee’s sons for any liberty interest to be implicated, 

and such a denial would likely flow 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 efficiency 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 court for reconsideration consistent with this opinion. Lee’s sentence is otherwise 

AFFIRMED. 
20 No. 19-1300 

ST. EVE, Circuit Judge, concurring in part. I agree with my 

colleagues that the district court correctly calculated Shawn 

Lee’s criminal history score and that Lee’s fine did not result 

from any error. I further agree that Supervised Release Condition No. 7 raises an issue of improper delegation of Article 

III power to a probation officer because of Lee’s underlying 

constitutionally protected liberty interest in associating with 

his 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 “subject 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 release 

is 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 two 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 special 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 disagree 

that a challenge to a properly preserved condition of supervised release is premature because the court or a probation 

officer would first 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 of 
No. 19-1300 21

the administration of Condition No. 7 was impermissible because of Lee’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 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 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 rehabilitation 

or prevent his recidivism, and instead dismissed Lee’s objection on the ground that probation would address it upon his 

release from custody. Given the 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. Accordingly, I would vacate the condition and remand to the district court not only to remedy the 

impermissible delegation, but also to carve out a limited exception to Condition No. 7 for Lee’s children, or to otherwise 

provide a sufficient rationale for their inclusion in the terms 

of the condition.