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 sen-
tence 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 drug-
trafficking 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 re-
ceives the probation officer’s permission. Because this super-
vision 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 meth-
amphetamine near Carlinville, Illinois. DEA agents confirmed
those reports by arranging a controlled buy between a confi-
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 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 con-
trolled 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 admit-
ted 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 ar-
rest. During that seven-month period alone, Lee distributed
No. 19-1300                                                          3

approximately 100 pounds (45.36 kilograms) of methamphet-
amine. 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 investiga-
tion, 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 prox-
imity 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 meth-
amphetamine with intent to distribute (Counts 2 and 3), and
one count of possessing firearms in furtherance of a drug-traf-
ficking 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 statu-
tory 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’ imprison-
ment on Count 2 and 60 months’ imprisonment on Count 4.
Neither party objected.
    The district judge sentenced Lee to 210 months’ imprison-
ment, consisting of 150 months on Count 2—a below-Guide-
lines sentence—and 60 months on Count 4, to be served con-
secutively. The judge further imposed a $20,000 fine—a be-
low-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 as-
sociation 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, su-
pervised release, imprisonment, work release, or escape sta-
tus.” This challenge lacks merit because Lee engaged in con-
duct 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, 

, 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 convic-
tion 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 ar-
gument misses the mark. Lee invokes language extracted
from the safety-valve provision at 18 U.S.C. § 3553(f): “Infor-
mation 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 re-
garding 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 fol-
lowing 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, 

,
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 below-
Guidelines 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 errone-
ous.” United States v. Artley, 

, 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, 

, 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, 

, 926–27 (7th Cir.
1994). The defendant’s burden here is a heavy one “because
almost everyone has or will acquire some assets.” 

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 defend-
        ant and his dependents relative to alternative
        punishments;
        (4) any restitution or reparation that the defend-
        ant has made or is obligated to make;
        (5) any collateral consequences of conviction, in-
        cluding civil obligations arising from the de-
        fendant’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 ex-
press or specific findings regarding each of the relevant fac-
tors, 

, although an express finding may
nonetheless be made by adopting the PSR’s facts, 

States v. Monem, 

, 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. 

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, 

, 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 rele-
vant 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 “mas-
sive 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 con-
sider the nature, circumstances, and seriousness of the of-
fense). She also underscored the need to deprive Lee of his ill-
gotten 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 de-
pendents, 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 com-
bined value exceeding the ultimate fine amount, including
Lee’s two automobiles and two all-terrain vehicles ($7,300 to-
tal), 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 sup-
porting the imposed fine. 

(citing 

).
    Because the district judge accepted the PSR’s factual find-
ings yet departed from the probation officer’s estimate re-
garding Lee’s ability to pay a fine, Lee insists the fine be va-
cated 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 re-
port 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 

.
    But Bauer’s language describes situations in which the dis-
trict court either imposes a fine inconsistent with its stated


     5The 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 re-
duced 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 or-
der. (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 ad-
dressing 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. 

We pointed to Monem as illustrative of the former, where the
probation officer recommended a below-Guidelines fine be-
cause of the defendant’s financial status. 

(discussing 

–12). But at Monem’s sen-
tencing, the judge stated: “The Court will accept the recom-
mendation of the presentence report and impose a fine of
$15,000, which is the minimum fine.” 

(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 state-
ment that it accepted the recommendation of the PSR when
an unexplained contradiction [was] evident from the record.”

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 argu-
ment from the parties regarding Lee’s financial status, rejected
the probation officer’s recommendation of no fine, and in do-
ing 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’ super-
vised release on each count of conviction, to be served con-
currently. Among the various terms of supervision, the judge
ordered Lee not to:
12                                                   No. 19-1300

       knowingly meet, communicate, or otherwise in-
       teract 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 two-
fold: first, Lee maintains the condition, as written, commits an
improper delegation of Article III power to the probation of-
ficer; 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-Ar-
ticle III judge, such as a probation officer or treatment pro-
vider.” United States v. Wagner, 

, 543 (7th Cir.
2017). At the outset, the government claims Lee did not pre-
serve 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, 

, 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, 

,
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 de-
fendant’s punishment.” 

(internal quo-
tation marks and citations omitted). An example of a permis-
sible, 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.” 

the district court delegated the decision of
whether Lee could associate with felons to the probation of-
ficer. 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 lan-
guage allowing a sex-offender-treatment provider to deter-
mine whether the defendant could access 

–43. Lee’s case also aligns with United States v.
Voelker, 

(3d Cir. 2007). The contested condition in
that case prohibited the defendant from associating with mi-
nors absent the probation officer’s prior approval. 

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.” 

14                                                           No. 19-1300

    The condition here is no different. Our colleague’s sepa-
rate 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. 

.
    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 set-
tings that jeopardize a supervisee’s progress. But the same ex-
pertise 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 in-
put 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.” 

and remand this condition for reassessment.6


     6We 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. Ar-
mour, 

, 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 se-
rious one. The liberty interest he raises—a parent’s right to
enjoy the companionship of his children—“is perhaps the old-
est of the fundamental liberty interests recognized by [the Su-
preme Court].” Troxel v. Granville, 

, 65 (2000).7 And
in no way do we diminish Lee’s liberty interest by comment-
ing 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 permis-
sion 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 de-
tracts from Lee’s claimed liberty interest. See Russ v. Watts, 

,
788 (7th Cir. 2005) (Observing several circuits have been “reluctant to ex-
tend 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 chil-
dren’s need for the guidance and support of their parents warrants
sharply different constitutional treatment.” 

(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’ impris-
onment (seventeen and a half years) and his terms of supervi-
sion will not take effect until his release. See United States v.
Kappes, 

, 859 (7th Cir. 2015) (holding claimed vio-
lation 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 

(recommending district
judges reassess defendants’ conditions of supervision on the
eve of release from prison; “A defendant may change substan-
tially during a long prison sentence, and the world outside the
prison walls may change even more.”); United States v. Siegel,

, 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 ex-
ample, Lee might rehabilitate his serious drug addiction (de-
tailed 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, 

, 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 recommen-
dation in hand, the judge will refuse permission to communi-
cate or associate with Ethan and Charles. And we assume the
probation officer will address requests to associate and make
recommendations in a reasonable manner. 

–58. At sentencing, the probation officer explained his de-
partment reviews requests to associate simply for whether the
desired interaction will “generate any additional risk for non-
compliance” 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) per-
mission 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 be-
tween Lee and his sons provided all parties are progressing
in their respective rehabilitative sentences. Receiving permis-
sion to associate, therefore, is largely up to all three men. See
United States v. Edwards, 

, 637 (7th Cir. 2019) (re-
jecting defendant’s vagueness challenge to a condition that
prohibited unauthorized contact with minors because de-
fendant 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, includ-
ing where the terms of supervision required the defendant to
submit to drug testing or to participate in sex offender treat-
ment, or prohibited the defendant from associating with
white supremacy groups or from using the internet entirely.
See United States v. Rhodes, 

, 629 (7th Cir. 2009)
(collecting cases). But the conditions in those cases were defi-
nite, 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 as-
sert his constitutional rights, 

, 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, 

, 389 (7th Cir. 2019). Our ap-
proach here promotes efficiency over “perpetuating expen-
sive and time-consuming appeals and resentencings … .”
United States v. Silvious, 

, 371 (7th Cir. 2008).
                        III. Conclusion
    For all these reasons, Condition No. 7 is VACATED and
REMANDED to the district court for reconsideration con-
sistent 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 cor-
rectly 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 condi-
tion infringes on his constitutionally protected interest in as-
sociating with his children. And while I agree with my col-
leagues that Supervised Release Condition No. 7 raises an is-
sue of improper delegation of Article III power to a probation
officer, in my view this is only because of this underlying con-
stitutionally 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 ex-
ception 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 del-
egation.
    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, 

, 859
(7th Cir. 2015), I do not believe this is such a case. The majority
cites United States v. Rhodes, 

(7th Cir. 2009), as an
example where we found a challenge to a supervised release
condition unripe. In Rhodes, the defendant contested a condi-
tion that he “undergo a psychosexual evaluation and partici-
pate in an outpatient sex offender counseling program if rec-
ommended by the evaluator which may involve use of poly-
graph and plethysmograph examinations.” 

Rhodes
objected to the examinations on general Fifth Amendment
grounds. 

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 counsel-
ing 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.” 

And in Kappes—another decision the majority cites—when a
defendant challenged a condition banning him from com-
municating 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 condi-
tion. 

. This condition was “too contin-
gent,” 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. 

contingencies are not at play in the condition
Lee challenges today. The disputed condition will set as a de-
fault 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 com-
municate 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 imposi-
tion 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, 

, 743 (7th Cir. 2017). We further
review whether the district court adequately explained a cho-
sen condition of supervised release de novo. 

majority notes, Lee correctly identifies that Condi-
tion 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 pro-
cess the right to familial relations.” Brokaw v. Mercer Cty., 

, 1018 (7th Cir. 2000) (citing Prince v. Massachusetts,

, 166 (1944); Meyer v. Nebraska, 

, 399
(1923); Santosky v. Kramer, 

, 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, 

, 484
(1990) (Scalia, J., concurring in part and dissenting in part); see
also Lassiter v. Dep’t of Soc. Servs., 

, 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, 

, 870 (7th Cir. 2015)
22                                                  No. 19-1300

(quoting United States v. Sines, 

, 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, 

, 496 (7th Cir.
2018). We further have explained that courts must consider
the infringement “more scrupulously” when it impacts deep,
personal relationships. 

–02.
    Here, the district court did not discuss why a bar on com-
municating with his children would aid in Lee’s rehabilitation
or prevent his recidivism, and instead dismissed Lee’s objec-
tion 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 con-
dition and remand to the district court to carve out a limited
exception to Condition No. 7 for Lee’s children, or to other-
wise provide a sufficient rationale for their inclusion in the
terms of the condition.
    Second, the majority concludes that any condition allow-
ing a probation officer to grant exceptions to a restriction pro-
hibiting probationers from associating with convicted felons
runs afoul of the non-delegation doctrine. As the majority rec-
ognizes, this holding contradicts our conclusion in Armour,
where we rejected an argument that “giving the probation of-
ficer the power to determine whether Armour has permission
to associate with convicted felons violates the non-delegation
principle.” 

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 de-
fendant’s punishment.’” United States v. Wagner, 

,
543 (7th Cir. 2017) (quoting United States v. Schrode, 

, 555 (7th Cir. 2016)). Probation officers frequently navi-
gate 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 of-
ficer’s domain: as the probationer’s supervisor, the probation
officer is aware of his compliance with conditions and pro-
gress during his period of release. Only because of the mag-
nitude 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 chal-
lenges the delegation on this narrow ground.
    Our opinions in Schrode and Wagner do not suggest other-
wise. In Schrode, we determined that the defendant waived his
nondelegation challenge by failing to raise it before the dis-
trict court. 

–56. Although we did not
reach the issue, we said in dicta that “a condition of sex of-
fender treatment ‘as deemed necessary by probation,’” trou-
bled us because it delegated to a probation officer “the under-
lying judgment of whether the condition will be imposed at
24                                                            No. 19-1300

all.” 

And in Wagner,1 we struck down a condition
that similarly allowed probation to determine “whether ac-
cess to adult pornography should…be restricted or denied.”

(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 excep-
tions. This is properly within probation’s “broad authority to
manage and supervise probationers.” 

.
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 im-

plicated 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 Amend-
ment protection. 

(citing United States v. Taylor, 

, 793 (7th Cir. 2015)).