United States of America v. Deon Pugh

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 24-1650
U NITED S TATES OF A MERICA,
Plaintiff-Appellee,
v.
DEON P UGH ,
Defendant-Appellant.
____________________
Appeal from the United States District Court for the
Northern District of Illinois, Eastern Division.
No. 18-CR-157-4 — Andrea R. Wood, Judge.
____________________
A RGUED A PRIL 9, 2025 — DECIDED A UGUST 13, 2025
____________________
Before EASTERBROOK, J ACKSON -A KIWUMI , and PRYOR , Cir-
cuit Judges.
PRYOR , Circuit Judge. Following a bench trial, the district
court convicted Deon Pugh of four counts, including conspir-
acy to distribute a controlled substance. After calculating the
applicable guidelines range at 360 months’ imprisonment to
life, the district court imposed a sentence of 216 months’ im-
prisonment followed by five years of supervised release.

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2 No. 24-1650
Pugh challenges the district court’s decisions at sentencing
to (1) designate him as a career offender; (2) attribute to him a
drug quantity of over 1,000 grams of heroin; and (3) apply a
four-level leadership enhancement. For the reasons below, we
affirm.
I. BACKGROUND
The government charged Pugh by superseding infor-
mation with four counts, including conspiracy to knowingly
and intentionally possess with intent to distribute and distrib-
ute a controlled substance in violation of 21 U.S.C. §§ 841(a)(1)
and 846 (Count I); knowingly and intentionally distributing a
controlled substance in violation of 21 U.S.C. § 841(a)(1) and
18 U.S.C. § 2 (Counts II and III); and possession of a firearm
as a felon in violation of 18 U.S.C. § 922(g)(1) (Count IV). The
superseding information alleged that from late 2017 through
early 2018, Pugh and eight co-defendants conspired to distrib-
ute illegal drugs from the home of Jonathan Mason, who the
parties agree served as a leader of the conspiracy. After Pugh
waived his right to a jury trial, the case proceeded to a bench
trial pursuant to Rule 23 of the Federal Rules of Criminal Pro-
cedure. The district court found Pugh guilty on all counts.
In relation to the conspiracy charge, the only conviction at
issue on appeal, the district judge concluded that the govern-
ment had proven beyond a reasonable doubt that Pugh par-
ticipated in a conspiracy with, “at a minimum,” six other in-
dividuals between September 2017 and March 2018. The dis-
trict court also concluded that the conspiracy’s possession
and distribution of more than 1,000 grams of heroin was rea-
sonably foreseeable to Pugh as a co-conspirator. In reaching
its verdict on this count, the district court found the testimony
of co-conspirator Derrick Wiltz credible, noting that Wiltz’s

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No. 24-1650 3
statements were corroborated by additional evidence pre-
sented at trial by the government including testimony from a
Federal Bureau of Investigation agent specializing in drug op-
erations, Special Agent Culloton; pictures of drug production
materials; Pugh’s own correspondence; and drugs seized
from Mason’s home. As the district court recounted, the evi-
dence established that Mason’s home served as the center of
the conspiracy’s drug activity; Pugh visited Mason’s home al-
most daily beginning in September 2017; Pugh would bring
drugs, including heroin, to Mason’s home and prepare the
drugs for sale; and Pugh directed Wiltz to deliver repackaged
drugs to customers. The district court further observed that
the relationship between Pugh and Mason was akin to that of
a “joint venture.”
After the district court denied Pugh’s motion for judgment
of acquittal under Federal Rule of Criminal Procedure 29, and
his alternative request for a new trial under Rule 33, the case
proceeded to sentencing.
Before sentencing, the United States Probation Office pre-
pared a Presentence Investigation Report (“PSR”). The proba-
tion officer who prepared the PSR calculated an offense level
of 38, based on a converted drug weight of approximately
15,774.12 kilograms and a four-level enhancement for Pugh
being an organizer or leader in the drug conspiracy. See
U.S.S.G. §§ 2D1.1, 3B1.1. The probation officer also calculated
that Pugh had accumulated 13 criminal history points and
was a career offender, both resulting in a criminal history cat-
egory of VI. See U.S.S.G. § 4B1.1(b). The PSR concluded that
Pugh’s criminal history and present conviction yielded an ad-
visory guideline range of 360 months to life imprisonment on
the conspiracy conviction.

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4 No. 24-1650
At sentencing in April 2024, the district court discussed
the PSR with the parties. Deviating from the probation of-
ficer’s drug quantity findings, the district court calculated a
base offense level of 30 by attributing to Pugh a converted
drug weight of 2,274.12 kilograms, which, relevant to this ap-
peal, included approximately 2,236.6 grams of heroin (repre-
senting a converted drug weight of 2,236.60 kilograms). The
district court then applied a four-level aggravating role en-
hancement upon concluding that Pugh held a leadership or
organizing role in the conspiracy, thereby raising Pugh’s of-
fense level to 34. See U.S.S.G. § 3B1.1(a). Finally, the court des-
ignated Pugh as a career offender under the Sentencing
Guidelines, raising his offense level to 37 with a criminal his-
tory category of VI. See U.S.S.G. § 4B1.1. The court calculated
Pugh’s final advisory guidelines range at 360 months to life.
The court sentenced Pugh to 216 months’ imprisonment with
five years of supervised release on April 9, 2024.
II. DISCUSSION
Pugh argues the district court erred in three respects at
sentencing. First, by designating him as a career offender. Sec-
ond, by attributing to him a drug quantity of over 1,000 grams
of heroin. And third, by applying a four-level leadership en-
hancement.
A. Career-Offender Designation
“A defendant is a career offender if (1) the defendant was
at least eighteen years old at the time the defendant commit-
ted the instant offense of conviction; (2) the instant offense of
conviction is a felony that is either a crime of violence or a
controlled substance offense; and (3) the defendant has at
least two prior felony convictions of either a crime of violence

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No. 24-1650 5
or a controlled substance offense.” U.S.S.G § 4B1.1(a). Pugh’s
challenge focuses on whether the term “controlled substance
offense” encompasses inchoate offenses such as conspiracy,
of which he was convicted.
Pugh acknowledges that the Sentencing Guidelines were
amended in November 2023 to expressly provide that a “con-
trolled substance offense” includes inchoate offenses such as
conspiracy. See U.S.S.G. § 4B1.2(d). Accordingly, Pugh con-
cedes that the version of the Guidelines in effect during his
sentencing in April 2024 warranted finding him a career of-
fender. However, Pugh urges that the sentencing judge
should have applied the Guidelines in effect when he com-
mitted his offense in 2017 and 2018, which would not have
warranted the career-offender designation. He maintains that
applying the harsher Guidelines adopted after he engaged in
the conspiracy violated the Constitution’s Ex Post Facto
Clause, U.S. C ONST. art I, § 9, cl. 3. See United States v. Vasquez-
Abarca, 946 F.3d 990, 994 (7th Cir. 2020). An “ex post facto vio-
lation” occurs “when a defendant is sentenced under Guide-
lines promulgated after he committed his criminal acts and
the new version provides a higher applicable Guidelines sen-
tencing range than the version in place at the time of the of-
fense.” Peugh v. United States, 569 U.S. 530, 533 (2013).
The problem with Pugh’s position is that he does not show
that the 2023 amendment to § 4B1.2 adversely affected him.
See United States v. Vallone, 752 F.3d 690, 694 (7th Cir. 2014).
Rather, under the law of our circuit, Pugh’s career-offender
designation was appropriate even before the 2023 amend-
ment given our deference to the Sentencing Commission’s
commentary in Application Note 1 to § 4B1.2, which in-
structed that the term “controlled substance offense”

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6 No. 24-1650
included “aiding and abetting, conspiring, and attempting to
commit such offenses.” United States v. White, 97 F.4th 532, 537
(7th Cir. 2024).
Pugh asks us to revisit this deference. He reasons that the
Supreme Court’s decision in Stinson v. United States, 508 U.S.
36 (1993), which served as the source of our deference to Ap-
plication Note 1, should no longer be viewed as good law.
Stinson held that the Sentencing Commission’s commentary
“is authoritative unless it violates the Constitution or a federal
statute, or is inconsistent with, or a plainly erroneous reading
of, that guideline.” 508 U.S. at 38. In Pugh’s view, Stinson
should be found overruled by Kisor v. Wilkie, 588 U.S. 558
(2019), in which case Pugh’s conviction for conduct in 2017
and 2018 would not have qualified as a controlled substance
offense under the version of § 4B1.2 in effect at that time.
Pugh’s argument cannot succeed. We recently held that
our deference to Application Note 1 remains on solid ground
because “Kisor did not unsettle Stinson.” White, 97 F.4th at 539.
As we explained, although Kisor did “reduce[] the level of def-
erence afforded to an agency’s interpretation of its own regu-
lations,” Kisor did not address the deference we afford to the
Sentencing Commission, which “is not an executive agency”
but instead “an independent commission within the judicial
branch.” Id. at 538–39. Absent a “compelling reason” to over-
rule this precedent, we cannot find Pugh’s career offender
designation erroneous. Id. at 538. Accordingly, we reject
Pugh’s position that his career-offender designation repre-
sents an ex post facto violation.

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No. 24-1650 7
B. Drug Quantity
Pugh also challenges the district court’s calculation of his
base offense level as 30 on the basis that the calculation im-
properly attributed to him over 1,000 grams of heroin. See
U.S.S.G. § 2D1.1(a)(3), (c)(5). The government argues Pugh
waived this challenge.
We agree with the government and find the challenge
waived. A defendant waives an argument that a sentencing
decision was erroneous when, before the district court, his
lawyer argued in favor of the sentencing decision that the de-
fendant seeks to challenge on appeal. United States v. Nichols,
789 F.3d 795, 796 (7th Cir. 2015). That is what happened here.
Pugh urged in his sentencing memorandum and in a supple-
mental sentencing memorandum that the proper base guide-
line level should be 30, based on a drug quantity of approxi-
mately 2,236 grams of heroin.1 For example, he asked the dis-
trict court to “not deviate” from its finding “that Mr. Pugh
trafficked in 2,236 grams of heroin” and represented that
2,236 “is the amount Mr. Pugh should be held accountable for
transacting.” Because Pugh expressed clear intent to not only
forgo a challenge to the 2,236-gram attribution, but to advo-
cate for that attribution, Pugh waived any challenge to the at-
tribution on appeal. See id.
C. Leadership Enhancement
Pugh’s remaining argument takes issue with the district
court’s application of a four-level leadership enhancement,
1 (Dkt. 1006, Sentencing Mem., at 4, 6); (Dkt. 1052-1, Supp. Sentencing
Mem., at 3–4, 6).

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8 No. 24-1650
which raised his offense level from 30 to 34. See U.S.S.G.
§ 3B1.1(a).
A four-level enhancement applies to a defendant who
“was an organizer or leader of a criminal activity that in-
volved five or more participants.” U.S.S.G. § 3B1.1(a). In con-
trast, a defendant who “was a manager or supervisor” re-
ceives an increase of three levels. U.S.S.G. § 3B1.1(b). Distinc-
tions between these enhancements are “matters of degree,”
with “an organizer or leader exercis[ing] more decision-mak-
ing and leadership authority, participat[ing] to a larger extent
in the planning or organizing of the offense, and exert[ing] a
greater degree of control over others.” United States v. Colon,
919 F.3d 510, 518 (7th Cir. 2019).
Relevant factors to consider in deciding whether to apply
a leader or organizer enhancement versus a manager or su-
pervisor enhancement include the “exercise of decision-mak-
ing authority, the nature of participation in the commission of
the offense, the recruitment of accomplices, the claimed right
to a larger share of the fruits of the crime, the degree of par-
ticipation in planning or organizing the offense, the nature
and scope of the illegal activity, and the degree of control and
authority exercised over others.” U.S.S.G. § 3B1.1, cmt. n.4.
This list is not exhaustive, and no factor is a prerequisite.
United States v. House, 883 F.3d 720, 724 (7th Cir. 2018); United
States v. Mankiewicz, 122 F.3d 399, 406 (7th Cir. 1997). Rather,
“the primary goal in applying § 3B1.1 should be to make a
commonsense judgment about the defendant’s relative culpa-
bility given his status in the criminal hierarchy.” House, 883
F.3d at 724 (internal quotations and citations omitted).
“When considering a challenge to an enhancement under
§ 3B1.1 of the Guidelines, we review de novo whether the

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No. 24-1650 9
factual findings of the district court adequately support the
application of the enhancement.” United States v. Craft, 99
F.4th 407, 414 (7th Cir. 2024). But “[w]e review the underlying
factual findings for clear error,” id., “accord[ing] ‘great defer-
ence’ to those findings,” United States v. Beechler, 68 F.4th 358,
368 (7th Cir. 2023) (quoting United States v. Lundberg, 990 F.3d
1087, 1097 (7th Cir. 2021)). “[F]actual findings at sentencing
need only be supported by a preponderance of the evidence.”
Beechler, 68 F.4th at 368. “We reverse a district court’s applica-
tion of a sentencing enhancement ‘only if we are left with a
definite and firm conviction that a mistake has been made.’”
Id. (quoting United States v. Lovies, 16 F.4th 493, 504 (7th Cir.
2021)). And because the difference between the organizer or
leader enhancement and manager or supervisor enhancement
is often a close question, “we give considerable deference” to
the district court’s decision as to which of the two enhance-
ments is the better fit. United States v. Jones, 56 F.4th 455, 494
(7th Cir. 2022).
The district court applied a four-level leadership enhance-
ment, reasoning that the record reflected that Pugh acted as a
joint venturer with Mason in the drug conspiracy and “was
involved in overseeing the obtaining of wholesale quantities
of the drugs,” “directing the activities of others,” “mixing
th[e] narcotics,” and “repackaging” the narcotics for sale. The
district court did not clearly err in reaching these factual find-
ings, which were sufficient for the district court to apply the
leadership enhancement.
Although Pugh argues his relative culpability paled in
comparison to Mason’s, we fail to find the district court’s
joint-venturer conclusion to be clearly erroneous. Rather, the
district court’s conclusion finds support in multiple

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10 No. 24-1650
conversations between Pugh and Mason which reflect collab-
oration and indicate that the two were on relatively equal
footing in the organization. To that end, we emphasize that
more than one person may qualify as a leader or organizer of
conspiracy. U.S.S.G. § 3B1.1, cmt. n.4. Accordingly, that Ma-
son was a leader does not foreclose Pugh from being deemed
a leader as well. To the contrary, the district court could rea-
sonably find that Pugh’s conversations and coordination with
Mason indicated that Pugh and Mason were similarly situ-
ated within the hierarchy of the organization, thereby sup-
porting the district court’s conclusion that Pugh acted as a
leader.
Likewise, the district court did not clearly err in finding
Pugh exercised control over the conspiracy when he directed
others. The district court found Wiltz credibly testified that
Pugh had told him “where to go” to conduct a drug sale, told
him “what to do”, and directed him on obtaining supplies
necessary for the drug business. Wiltz further reported that
Pugh was one of the individuals he would “bring [money]
back to.” The trial evidence also reflects that Pugh directed
two other co-conspirators, Ryan Pearson and Alvin Williams,
by instructing them on various occasions to weigh drugs and
report that weight back to him. Because “giving orders” is a
“characteristic consistent with someone in a leadership role,”
the district court properly found this evidence relevant.
United States v. Longstreet, 567 F.3d 911, 926 (7th Cir. 2009)
(emphasis omitted). And that Pugh did not “exercise com-
plete dominion over every member of the enterprise at all
times” does not foreclose a finding that the enhancement
should apply. United States v. Garcia, 948 F.3d 789, 806 (7th Cir.
2020).

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No. 24-1650 11
As the district court’s factual findings were not clearly er-
roneous and adequately supported application of the en-
hancement, we affirm the district court’s application of the
leadership enhancement.
III. CONCLUSION
For these reasons, we AFFIRM.

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