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 

____________________ 

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 

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 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 violates the rule against delegating Article III 

power, 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 

to dealing pounds of drugs from about June 2017 until his arrest. During that seven-month period alone, Lee distributed 
No. 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 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, 

resulting in a total offense 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. The government did not charge Lee’s 

possession of that gun. 
4 No. 19-1300 

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 gains 

against Lee’s available assets. Upon release, the judge ordered 

Lee to a term of five 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 substantially 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 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 that 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 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, 

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 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 

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. 

 
No. 19-1300 7

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 

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 
8 No. 19-1300 

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 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 

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. 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. 

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 
10 No. 19-1300 

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 

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 

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

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. 

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: 
12 No. 19-1300 

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: first, Lee maintains the condition, as written, commits an 

improper delegation of Article III power to the probation officer; 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 constitutional authority to delegate 

the duty of imposing a defendant’s punishment to a non-Article 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 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). 
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 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. 

But here, the district court delegated the decision of 

whether Lee could associate with felons 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 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-offender-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 in 

that case prohibited the defendant from associating with minors absent the probation officer’s prior approval. Id. at 153. 

The Third Circuit vacated the condition because it anointed 

the probation officer with “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.” Id. at 154. 
14 No. 19-1300 

The condition here is no different. Our colleague’s separate opinion submits the probation officer cannot determine 

whether a condition should go into effect but can nevertheless

“manage,” i.e., allow, exceptions to the condition. We fail to 

see the functional difference. Article III does not confer upon 

the probation officer 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 officer” 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 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 Article III power. 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.” 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 Schrode
No. 19-1300 15

2. Familial Association 

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).7 And 

in 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 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 

(2016) and Wagner (2017). These two subsequent opinions make clear that 

decisions of whether to enforce certain components of a sentence cannot be 

delegated to the probation officer. Probation officers cannot grant permission to associate when a condition of supervised release bars association 

otherwise. Only Article III judges can make that call. 

7 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 

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 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 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 
No. 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 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 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 
18 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 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). 

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. 
No. 19-1300 19 

 

ST. EVE, Circuit Judge, dissenting in part and 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 disagree, however, 

that Lee’s challenge to Condition No. 7 is prospective such 

that it precludes our review of Lee’s argument that the condition infringes on his constitutionally protected interest in associating with his children. And while I agree with my colleagues that Supervised Release Condition No. 7 raises an issue of improper delegation of Article III power to a probation 

officer, in my view this is only because of this underlying constitutionally protected liberty interest. Therefore, while I also 

vote to vacate this condition and remand to the district court, 

I would do so only on the limited issue of carving out an exception to Supervised Release Condition No. 7 or providing a 

sufficient explanation for it. I write separately as to Section 

II.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 contingent 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 this 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 offender 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 possible 
20 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 occurred, the examinations had to 

be utilized. We therefore held that Rhodes’s objection to the 

examination was premature—Rhodes “may only be affected 

by the condition after a string of contingencies.” Id. at 629. 

And in Kappes—another decision the majority cites—when a 

defendant 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 not at play in the condition 

Lee 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 five years. 

Unlike the conditions challenged in Rhodes and in Kappes, 

nothing must first occur before that condition goes into effect: 

as soon as his supervised release begins, he may not speak 

with his (currently existing) children. 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. 
No. 19-1300 21

Because I do not view Lee’s challenge as prospective, I 

would resolve it on the merits. While we review “the imposition of an objected-to condition of supervised release for 

abuse of discretion,” “[t]he constitutionality of a condition of 

release is a legal determination we review de novo.” United 

States v. Shannon, 851 F.3d 740, 743 (7th Cir. 2017). We further 

review whether the district court 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 his children. “The Supreme Court 

has 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 opportunity 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 parent’s desire for and right to the 

companionship, care, custody and management of his or her 

children is an important interest.” (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 of the 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 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 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. 

Second, the majority concludes that any condition allowing a probation officer to grant exceptions to a restriction prohibiting probationers from associating 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 felons 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 ‘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.’” United States v. Wagner, 872 F.3d 535, 

543 (7th Cir. 2017) (quoting United States v. Schrode, 839 F.3d 

545, 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 numerous places where they might 

encounter convicted felons in their communities and beyond. 

This responsibility appropriately belongs in a probation officer’s domain: as the probationer’s supervisor, the probation 

officer 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 his 

nondelegation 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 dicta 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 at 
24 No. 19-1300 

all.” Id. at 556. And in Wagner,

1 we struck down a condition 

that similarly allowed probation to determine “whether access to adult pornography should...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 effect in the first instance, the 

condition 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 remand 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 pornography, which receives First Amendment protection. Wagner, 872 F.3d at 542 (citing United States v. Taylor, 796 

F.3d 788, 793 (7th Cir. 2015)).