Deandre Cherry v. United States
CourtCourt of Appeals for the Seventh Circuit
Date FiledNovember 5, 2026
Docket21-2231
JudgeSykes
StatusPublished
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Full Opinion
In the
United States Court of Appeals
for the Seventh Circuit
____________________
No. 21-2231
DEANDRE CHERRY,
Petitioner-Appellant,
v.
UNITED STATES OF AMERICA,
Respondent-Appellee.
____________________
Appeal from the United States District Court for the
Northern District of Illinois, Eastern Division.
No. 20 CV 4752 — Ronald A. Guzmán, Judge.
____________________
ARGUED DECEMBER 5, 2024 — DECIDED NOVEMBER 5, 2026
____________________
Before ROVNER, SYKES, and ST. EVE, Circuit Judges.
SYKES, Circuit Judge. With the help of a confidential inform-
ant, federal agents from the Drug Enforcement Administra-
tion (“DEA”) arrested DeAndre Cherry for possessing heroin
with intent to distribute. A jury found him guilty of that
crime. This was not Cherry’s first drug offense: In 2003 he was
convicted in Illinois state court of manufacturing or deliver-
ing cocaine. Based on that conviction (and others), the district
judge applied the enhanced statutory penalties under
2 No. 21-2231
21 U.S.C. § 841(b)(1)(B) for defendants with “a prior convic-
tion for a felony drug offense.” 1 The judge also applied a sep-
arate enhancement under § 4B1.1(a) of the Sentencing Guide-
lines, which subjects career offenders to an increased advisory
sentencing range. 2 As a result, Cherry was sentenced to
20 years in prison—10 years above the 10-year statutory min-
imum but 10 years below the low end of the applicable Guide-
lines range of 30 years to life. His sentence also included the
minimum 8-year term of supervised release.
We affirmed Cherry’s conviction on direct appeal, and his
case now returns to us on postconviction review under
28 U.S.C. § 2255. Cherry raises two Sixth Amendment claims
for ineffective assistance of counsel under the rubric of
Strickland v. Washington, 466 U.S. 668 (1984). He first chal-
lenges his trial counsel’s failure to object to the sentencing en-
hancements. He also argues that his trial and appellate attor-
neys were constitutionally ineffective for failing to object to
the testimony of Special Agent David Brazao, who recounted
incriminating details that the agents learned from the confi-
dential informant.
The government agrees that Cherry’s counsel should have
challenged at least the statutory sentencing enhancement, but
it denies that Cherry suffered any prejudice. Because Cherry’s
sentence falls well below the applicable Guidelines range, the
1 The current version of § 841(b)(1)(B) applies to offenders who have pre-
viously committed either “a serious drug felony or [a] serious violent fel-
ony.” We refer to the version in effect in 2016, when the probation office
prepared Cherry’s initial presentence report.
2 The presentence report references the 2015 version of the Sentencing
Guidelines. We do the same.
No. 21-2231 3
government maintains that counsel’s failure to object to either
enhancement was inconsequential. The government also ar-
gues that the evidence against Cherry was so overwhelming
that Agent Brazao’s testimony couldn’t have influenced the
jury’s verdict.
We agree, but only in part. Counsel’s failure to object to
the § 841(b)(1)(B) statutory enhancement prejudiced Cherry
because it increased both the advisory Guidelines range and
the mandatory minimum terms of imprisonment and super-
vised release. But the remaining ineffective-assistance claims
are meritless. Our decision in United States v. Ruth, 966 F.3d
642 (7th Cir. 2020), dooms the claim centered on the applica-
tion of the § 4B1.1 career-offender enhancement, and the ad-
mission of Agent Brazao’s testimony did not prejudice
Cherry’s defense. We vacate his sentence and remand for re-
sentencing.
I. Background
A complete description of the facts leading to Cherry’s ar-
rest and conviction is contained in our prior opinion and
won’t be repeated here. United States v. Cherry, 920 F.3d 1126
(7th Cir. 2019). While investigating the importation of cocaine
from Mexico into Chicago, DEA agents arrested a man who
was attempting to collect 26 kilograms of cocaine near O’Hare
International Airport. After his arrest, the man informed the
agents that he planned to deliver half the cocaine to Cherry—
whom he knew only as “Mo.” At the agents’ suggestion, the
man agreed to serve as a confidential informant and assist
them with a sting operation.
The informant told the agents that he knew Cherry from
prior drug transactions and that the pair planned to meet that
4 No. 21-2231
evening at Cherry’s home in Harvey, Illinois. Cherry was an
average-height and average-weight black man, the informant
reported, and he drove a white Mercedes SUV.
The agents concocted a sting operation in which the in-
formant would conceal sham cocaine in a hidden compart-
ment in his red Volkswagen Jetta and ask Cherry to change
their meeting location to a nearby parking lot in Markham,
Illinois. Once Cherry confirmed his interest in the cocaine, the
informant would step out of the car as a signal to the agents
that the transaction was complete.
That’s exactly what happened. At the appointed time, a
2012 white Mercedes SUV entered and circled the parking lot,
pulling up next to the informant’s Jetta. Cherry emerged from
the SUV and entered the Jetta’s front passenger side. The in-
formant told Cherry that he had hidden the cocaine in a com-
partment in the back of the car, and Cherry responded that he
wanted to see it. At that point the informant exited the car,
signaling to the agents that Cherry had accepted the sham co-
caine. Almost a dozen agents immediately swarmed the Jetta
while Cherry darted into his SUV, trying to flee the scene. He
was unsuccessful; the agents pulled Cherry out of the SUV
and arrested him.
As one agent returned to the SUV, he spotted an open
black satchel in plain view on the front passenger seat; spill-
ing out of the satchel were clear baggies of what appeared to
be either heroin or cocaine. Testing confirmed that it was a
combination of both: The baggies contained 348.1 grams of
heroin and 13.7 grams of crack cocaine. The agents also found
$19,495 stashed in the satchel and the SUV’s center console.
No. 21-2231 5
Cherry told the agents that three weeks earlier, the inform-
ant had fronted him half a kilogram of low-quality heroin. His
customers complained, so Cherry had asked to exchange the
remaining heroin for cocaine. He and the informant were
meeting to make the exchange when the agents moved in and
arrested him.
Cherry was indicted for possessing 100 or more grams of
heroin with intent to distribute. See 21 U.S.C. § 841(a)(1). After
four years of protracted litigation over the lawfulness of
Cherry’s arrest and the search of his SUV—the details of
which are not relevant here—the case proceeded to a three-
day jury trial.
The prosecutor called several DEA agents to testify about
the sting operation and the evidence recovered in Cherry’s
SUV. Particularly important here is the testimony of Special
Agent David Brazao, the government’s first witness. During
his direct examination, Agent Brazao recounted much of what
we just described, though he did not disclose the details of the
DEA’s arrangement with the confidential informant. On
cross-examination, however, defense counsel asked Brazao
about the instructions given to the informant and whether it
was possible that the black satchel had actually been found in
the informant’s Volkswagen Jetta.
In light of these questions, the prosecutor argued that de-
fense counsel had opened the door to further testimony about
the informant. The district judge agreed. So on redirect exam-
ination, Agent Brazao testified about the informant’s arrest,
the planned sting operation, and the informant’s relationship
with Cherry—specifically, that the informant had “dealt with
[Cherry] in the past” and had been to his residence “to do
other transactions.” The informant also told the agents that
6 No. 21-2231
Cherry was a black male who drove a white Mercedes.
Cherry’s counsel did not object to this testimony.
At the close of evidence, the judge gave the jury the fol-
lowing limiting instruction: “You have heard testimony from
Agent Brazao … about statements made by an informant to
agents. Those statements should be considered only for the
purpose of explaining the actions of the agents, and you may
not consider it for any other purpose.” After about two hours
of deliberation, the jury returned a guilty verdict.
In advance of Cherry’s sentencing hearing, the probation
office prepared a presentence report (“PSR”) calculating the
advisory Guidelines range. Two aspects of that calculation are
at issue here. First, the PSR applied the heightened statutory
penalties for repeat offenders under § 841(b)(1)(B). The ver-
sion of that provision then in effect stated that a defendant
who violates § 841(a)(1) “after a prior conviction for a felony
drug offense” shall be sentenced to a prison term of not “less
than 10 years” and “a term of supervised release of at least
8 years.” § 841(b)(1)(B) (2016). The baseline minimum pen-
alty, by contrast, was 5 years in prison and at least 4 years of
supervised release. Id. As the government charged in an in-
formation, Cherry’s qualifying predicate was a 2003 Illinois
conviction for manufacturing or delivering cocaine. See
720 ILL. COMP. STAT. 570/401; 21 U.S.C. § 851(a)(1) (requiring
the government to file an information stating “in writing the
previous convictions to be relied upon”).
Second, the PSR applied the career-offender enhancement
set forth in § 4B1.1 of the Sentencing Guidelines. Under
§ 4B1.1(a), a defendant qualifies as a career offender if, among
other things, he “has at least two prior felony convictions of
either a crime of violence or a controlled substance offense.”
No. 21-2231 7
Cherry’s criminal history is extensive. Along with the cocaine-
trafficking conviction we’ve just mentioned, he was convicted
in 2003 of possessing a machine gun. And in 1993 he was con-
victed of two counts of attempted murder and one count of
armed robbery; the sentences for these three 1993 offenses
were imposed the same day. (The importance of that fact will
become clear when we turn to the claim centered on this en-
hancement.) Without the career-offender enhancement,
Cherry would have been placed in criminal-history
category V with an offense level of 24; with it, he was placed
in category VI with an offense level of 37. § 4B1.1(b)(1).
Cherry’s offense level and criminal-history category
yielded an advisory Guidelines range of 30 years to life. De-
fense counsel objected to that recommendation, arguing that
Cherry’s personal circumstances and single new offense
didn’t justify the application of the § 4B1.1 career-offender en-
hancement; she did not, however, contest that Cherry quali-
fied as a career offender. She likewise did not contest the ap-
plication of the § 841(b)(1)(B) statutory enhancement.
The district judge adopted the PSR with a few modifica-
tions that aren’t important here. The prosecutor then advo-
cated for a 20-year sentence, arguing that Cherry’s serious
criminal history warranted a steep sentence. Defense counsel
urged the judge to impose the 10-year mandatory minimum.
The judge ultimately followed the prosecutor’s recom-
mendation. Even setting aside the career-offender enhance-
ment, he explained, Cherry had numerous prior convic-
tions—some for violent offenses—and many more encounters
with law enforcement. The judge found that there was a
“great likelihood” that Cherry would return to committing
crimes, so a “substantial period of incarceration” was
8 No. 21-2231
necessary to protect the community. He accordingly imposed
a 20-year term of imprisonment and, as § 841(b)(1)(B) re-
quires, an 8-year term of supervised release.
Cherry appealed, asserting that the agents lacked proba-
ble cause to arrest him and to search both his SUV and the
satchel inside it. He further accused the government of violat-
ing its affirmative duty to disclose evidence under Brady v.
Maryland, 373 U.S. 83 (1963). We rejected all three challenges
and affirmed Cherry’s conviction. United States v. Cherry,
930 F.3d 1126 (7th Cir. 2019).
After his unsuccessful direct appeal, Cherry sought collat-
eral review in a pro se motion under § 2255. His 86-page hand-
written motion, along with two subsequently filed motions to
amend, raised a total of nine claims for relief. Only two
Strickland claims are relevant here. Cherry argued that his trial
and appellate counsel should have challenged the use of his
2003 Illinois drug conviction as a predicate for the statutory
and Guidelines sentencing enhancements. He also challenged
his trial counsel’s failure to call the confidential informant as
a witness after the informant’s out-of-court statements were
admitted through Agent Brazao.
The district judge denied relief, holding that Cherry’s state
convictions for attempted murder, armed robbery, and
cocaine trafficking supported the statutory and Guidelines
sentencing enhancements, so counsel’s failure to object was
neither a mistake nor prejudicial. The judge also concluded
that Cherry’s trial attorney reasonably declined to call the in-
formant, whose testimony likely would have been damaging
to Cherry.
No. 21-2231 9
Cherry appealed, and we granted a certificate of appeala-
bility on the question of counsel’s effectiveness with respect
to the statutory sentencing enhancement. We then appointed
counsel and later granted counsel’s motion to expand the cer-
tificate of appealability to include the question of counsel’s
failure to object to the career-offender enhancement and the
admission of the informant’s out-of-court statements through
Agent Brazao’s testimony.
II. Discussion
To prove a violation of his Sixth Amendment right to the
effective assistance of counsel, Cherry must show that his
counsel’s performance “fell below an objective standard of
reasonableness” and that the deficient performance preju-
diced his defense. Strickland, 466 U.S. at 688, 691. The preju-
dice element of the familiar Strickland standard requires
Cherry to demonstrate a “reasonable probability that, but for
counsel’s unprofessional errors, the result of the proceeding
would have been different.” Id. at 694. For his claim of trial
error, there must be a reasonable probability that “the fact-
finder would have had a reasonable doubt respecting guilt.”
Id. at 695. For his claim of sentencing error, there must be a
reasonable probability that “the judge would have imposed a
lower sentence.” Day v. United States, 962 F.3d 987, 992 (7th
Cir. 2020). These are legal questions, and our review of the
district judge’s decision is de novo. Harris v. United States,
13 F.4th 623, 627 (7th Cir. 2021).
A. Section 841(b)(1)(B) Enhancement
Cherry first challenges his trial counsel’s failure to object
to the § 841(b)(1)(B) statutory enhancement, which at the time
applied to any § 841(a)(1) offender with “a prior conviction
10 No. 21-2231
for a felony drug offense.” Invoking our 2020 decision in
United States v. Ruth, Cherry asserts that his Illinois cocaine-
trafficking conviction is not a qualifying “felony drug of-
fense” as § 841(b)(1)(B) uses that term. It follows, he argues,
that his counsel’s failure to object to the statutory enhance-
ment was deficient performance that prejudiced his defense.
Our holding in Ruth is unambiguous and squarely on
point: The definition of cocaine under Illinois law “is categor-
ically broader than the federal definition”; the state-law defi-
nition includes “optical, positional, and geometric” cocaine
isomers, 720 ILL. COMP. STAT. 570/206(b)(4), whereas the fed-
eral definition includes only “optical and geometric isomers,”
21 U.S.C. § 812, Schedule II(a)(4). Ruth, 966 F.3d at 647. So ap-
plying the required categorical approach, a cocaine-based
conviction under section 401 of the Illinois Controlled Sub-
stances Act is “not a predicate ‘felony drug offense’” for pur-
poses of a § 841(b)(1) sentencing enhancement. Id. at 650.
That said, our decision in Ruth postdated Cherry’s sen-
tencing hearing by almost three years. That’s potentially a
problem for Cherry: We have long recognized that the “Sixth
Amendment does not require counsel to forecast changes or
advances in the law.” Lilly v. Gilmore, 988 F.2d 783, 786 (7th
Cir. 1993). We have also recognized, however, that “there are
some circumstances” in which an argument “is sufficiently
foreshadowed in existing case law” such that counsel “may
be obliged to make, or at least to evaluate” it. Bridges v. United
States, 991 F.3d 793, 804 (7th Cir. 2021).
Applying the latter rule, we concluded in Coleman v.
United States that defense counsel should have known that a
categorical challenge to the use of an Illinois cocaine convic-
tion to support a § 841(b)(1) enhancement was potentially
No. 21-2231 11
available long before we decided Ruth. 79 F.4th 822, 831 (7th
Cir. 2023). By 2017 “the categorical approach was well-
established,” and at least one circuit had already applied the
approach to the federal definition of “felony drug offense.”
Harris, 13 F.4th at 629–30 (citing United States v. Ocampo-
Estreda, 873 F.3d 661, 667 (9th Cir. 2017)). We thus held that it
would have been objectively unreasonable for counsel not to
have “even considered a categorical challenge” to the use of pe-
titioner’s prior Illinois cocaine convictions as a basis to en-
hance his sentence under § 841(b)(1). Coleman, 79 F.4th at 832.
Relying on Coleman, Cherry argues that his counsel’s sen-
tencing advocacy was objectively unreasonable. There, as
here, trial counsel did not raise a categorical challenge to the
application of the § 841(b)(1) sentencing enhancement based
on an Illinois cocaine conviction; and there, as here, “the
framework for making such a challenge had been estab-
lished” by the time of sentencing. Id. at 831–32.
The government doesn’t disagree. Indeed, based on our
holding in Coleman, the government concedes that trial coun-
sel’s performance was deficient. 3
We accept that concession, though we note that Coleman
now stands on shaky ground. In Neal v. United States, we re-
jected the argument that under Coleman, an attorney who fails
to consider a categorical challenge to a § 841 enhancement
“necessarily provide[s] constitutionally ineffective assistance.”
155 F.4th 678, 686 (7th Cir. 2025) (emphasis added). As we
3 The government initially argued that Cherry waived his categorical chal-
lenge by failing to raise it in his § 2255 motion. But it has since retracted
that argument, acknowledging that Cherry’s pro se motion cited Ruth for
the proposition that Illinois’s definition of cocaine “is categorically
broader than the federal definition of a felony drug offense.”
12 No. 21-2231
explained, the petitioner in Coleman faced a harsh, binary sen-
tence—“life or not”—which distinguished that case from any
other in which “a wider set of outcomes is possible.” Id. at 687.
We also identified other decisions that called Coleman’s rea-
soning into question. See id. (citing Harris, 13 F.4th at 630;
White v. United States, 8 F.4th 547, 557 (7th Cir. 2021)). Sum-
ming up, we held that every case requires “an objective as-
sessment of counsel’s performance,” considering all the op-
tions “available to the defense.” Id. at 687–88 (quotation omit-
ted).
Our decision in Elion v. United States picked up where Neal
left off. 155 F.4th 889 (7th Cir. 2025). We explained that a broad
reading of Coleman’s holding was “misaligned with our
Strickland jurisprudence.” Id. at 905 (quotation omitted).
Coleman thus must be read contextually and narrowly—in
other words, as holding that “only egregious errors amount
to deficient performance.” Id. With that background under-
standing in mind, we articulated the governing standard this
way: Counsel performs deficiently only if an argument was so
clearly foreshadowed in existing law “that no reasonable at-
torney would fail to make it.” Id. at 906. We emphasized that
Coleman “sits at the outer boundary of that test.” Id.
Still, the government has not retracted its Coleman-based
concession or asked us to consider how Neal and Elion bear on
this case. We thus assume that Cherry’s trial counsel per-
formed deficiently by failing to challenge the § 841(b)(1)(B)
statutory enhancement.
On the question of prejudice, the government insists that
the § 841(b)(1)(B) sentencing enhancement did not affect the
outcome here because the judge imposed a 20-year prison
term—10 years below the Guidelines range of 30 years to life.
No. 21-2231 13
Accordingly, as the government sees things, there is no reason
to think that the statutory enhancement influenced the sen-
tence the judge chose.
We disagree. As already mentioned, § 841(b)(1)(B) pre-
scribes increased minimum and maximum penalties for of-
fenders with qualifying prior convictions. More specifically,
repeat offenders must be sentenced to a term of 10 years to life
in prison—up from the baseline minimum term of 5 years and
maximum of 40 years in prison. § 841(b)(1)(B). The statute also
increases the minimum term of supervised release to
8 years—twice the ordinary 4-year minimum. Id.
That’s not all. Section 4B1.1 of the Guidelines, which we’ll
discuss in greater detail later, assigns an offense level of 37 to
any career offender facing a maximum sentence of life in
prison. § 4B1.1(b)(1). A defendant subject to the typical 40-
year maximum, by contrast, is assigned an offense level of 34.
Id. The upshot of this three-level increase is significant: As
applied to Cherry, an offense level of 34 would have yielded
an advisory sentencing range of 262 to 327 months in prison.
His range, which was based on an offense level of 37, was
360 months to life.
In these circumstances, the application of the § 841(b)(1)(B)
enhancement prejudiced Cherry. As the Supreme Court has
explained, the Sentencing Guidelines “are not only the start-
ing point for most federal sentencing proceedings but also the
lodestar”; they “inform and instruct the district court’s deter-
mination of an appropriate sentence.” Molina-Martinez v.
United States, 578 U.S. 189, 200 (2016). Accordingly, in most
cases a defendant who establishes that the district judge mis-
takenly started from “an incorrect, higher Guidelines range
has demonstrated a reasonable probability of a different
14 No. 21-2231
outcome.” Id. Or as we put it in Coleman, “absent unusual cir-
cumstances,” a “reasonable probability of prejudice is pre-
sumed.” 79 F.4th at 832; see United States v. Duncan, 185 F.4th
761, 768 (7th Cir. 2026) (“[E]rrors that impact the Guidelines
range are presumptively prejudicial.”).
Setting the Guidelines aside, the lengthier minimum and
maximum statutory penalties confirm that counsel’s failure to
object was prejudicial. “Statutory minima and maxima have
an obvious anchoring effect on the judge’s determination of a
reasonable sentence” because “they demarcate the range
within which the judge may impose a sentence.” United States
v. Currie, 739 F.3d 960, 966 (7th Cir. 2014); see United States v.
Wilkinson, 139 F.4th 583, 590 (7th Cir. 2025). With this “anchor-
ing” assumption in mind, the district judge may have chosen
a lower sentence had he understood that the ordinary mini-
mum and maximum penalties applied.
The government reads the record differently, insisting that
Cherry’s 20-year sentence had little (if anything) to do with
the statutory and Guidelines ranges. In the government’s
view, the § 3553(a) sentencing factors—and particularly
Cherry’s lengthy criminal record—predominantly influenced
the judge’s decision to impose a term of 20 years in prison.
A district judge’s sentencing explanation is sometimes suf-
ficient to rebut the presumption of prejudice, but only when
the judge makes clear that the sentence is based “on factors
independent of the Guidelines.” Molina-Martinez, 578 U.S. at
200. Put another way, when the judge expressly states that he
“would have imposed the same sentence” regardless of any
potential error in the Guidelines calculation, there is no rea-
son to vacate the defendant’s sentence and remand for resen-
tencing. United States v. Gibson, 996 F.3d 451, 466 (7th Cir.
No. 21-2231 15
2021); see United States v. Robinson, 165 F.4th 1043, 1053 (7th
Cir. 2026).
Here, however, it’s not clear that the judge would have im-
posed the same 20-year sentence had he known the correct
sentencing ranges. He certainly didn’t say as much. It’s true,
as the government argues, that the judge emphasized
Cherry’s criminal history. He explained that even “[l]eaving
aside all career offender considerations,” Cherry’s criminal-
history score was concerning, reflecting his “multiple prior
convictions” and “many encounters with the law.” But this
vague reference to Cherry’s criminal record does not confirm
that the judge thought the 20-year sentence was appropriate
“irrespective of” the § 841(b)(1)(B) enhancement. Molina-
Martinez, 578 U.S. at 200. On this record, the judge’s sentenc-
ing remarks are not enough to overcome the ordinary pre-
sumption of prejudice. See United States v. Rollins, 836 F.3d
737, 743 (7th Cir. 2016) (enforcing the presumption even
though the defendant’s sentence was “below the correctly cal-
culated range once the career-offender error [was] removed”).
Besides, the government concedes that trial counsel’s fail-
ure to object to the § 841(b)(1)(B) enhancement prejudiced
Cherry in at least one way—namely, in the imposition of an
8-year term of supervised release. This concession is appro-
priate. The record gives us no clue as to what the judge might
have done had he known that Cherry was subject to a 4-year
minimum rather than an 8-year minimum term of supervised
release. And key to the prejudice analysis here, Cherry’s 8-
year term of supervised release is part of the same “sentenc-
ing package” as his 20-year prison term. We see no basis to try
to disentangle the prejudice traceable to each aspect of
Cherry’s sentence.
16 No. 21-2231
We’re especially hesitant to do so because the judge may
wish to reconfigure Cherry’s overall sentence on remand in
order “to achieve the goals [he] had in mind at the original
sentencing.” United States v. Wilcher, 91 F.4th 864, 875 (7th Cir.
2024). To be sure, there’s no guarantee that the judge will im-
pose a different—or even a lesser—sentence, and the govern-
ment is free to argue that Cherry’s criminal history justifies
reimposition of the original sentence. Still, Cherry has shown
a reasonable probability of a lower sentence without the
§ 841(b)(1)(B) enhancement. He has accordingly satisfied
Strickland’s prejudice standard and is entitled to resentenc-
ing. 4
B. Section 4B1.1 Guidelines Enhancement
We reach a different conclusion on counsel’s failure to ob-
ject to the career-offender enhancement under § 4B1.1 of the
Guidelines. A defendant qualifies as a career offender if:
(1) he was over the age of 18 at the time of the “offense of con-
viction”; (2) the offense of conviction qualifies as “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 or a controlled substance offense.”
U.S.S.G. § 4B1.1(a). There’s no dispute that Cherry satisfies the
first two conditions. He was in his mid-30s when he was ar-
rested in the sting operation, and possession with intent to
distribute heroin qualifies as a “controlled substance offense”
under § 4B1.1. See id. § 4B1.2(b) (defining that term).
4 We thus do not consider Cherry’s alternative—and extremely specula-
tive—argument that he would have been more likely to plead guilty and
receive a lower sentence had he known the correct Guidelines range.
No. 21-2231 17
Cherry’s claim turns on the third element—whether he
had been twice convicted of “a crime of violence or a con-
trolled substance offense.” § 4B1.1(a). He was convicted in
1993 of attempted murder and armed robbery. But because
his sentences for these crimes were imposed on the same day,
they count as a single conviction. § 4B1.2(c); § 4A1.2(a)(2).
And as we’ve already discussed, Cherry’s record also in-
cludes 2003 Illinois convictions for manufacturing or deliver-
ing cocaine and possessing a machine gun. He contends that
neither qualifies as a crime of violence or a controlled-
substance offense, so his counsel should have objected to the
§ 4B1.1 career-offender enhancement. The failure to do so, he
argues, deprived him of his Sixth Amendment right to the ef-
fective assistance of counsel.
Our decision in Ruth forecloses this claim. There we held
that § 4B1.2’s definition of “controlled substance offense”
does not incorporate the “federal definition of controlled sub-
stance” found in the Controlled Substances Act. 966 F.3d at
651–52. Rather, the Guidelines career-offender provisions de-
fine “controlled substance offense” to include all state-law
drug-trafficking offenses that involve “behavior-altering or
addictive drugs” and that are punishable by at least one year
in prison. Id. at 654 (quotation omitted); see § 4B1.2(b). Given
the breadth of that definition, we concluded that a cocaine-
based conviction under Illinois law plainly qualifies as a
controlled-substance offense for purposes of the career-
offender enhancement. Ruth, 966 F.3d at 654.
Because Ruth had not yet been decided at the time of his
sentencing hearing, Cherry argues that a timely objection to
the application of the career-offender enhancement may have
led to a favorable decision in the district court or on appeal.
18 No. 21-2231
We’re skeptical. It’s true that some of our sister circuits have
embraced Cherry’s preferred reading of § 4B1.2 and con-
cluded that the Guidelines incorporate the federal definition
of “controlled substance.” Ruth, 966 F.3d at 653. But as we ex-
plained in Ruth, our holding was heavily informed—if not
foreordained—by our prior decision in United States v.
Hudson, which held that “controlled-substance offenses in-
clude state-law offenses related to controlled or counterfeit
substances punishable by imprisonment for a term exceeding
one year,” 618 F.3d 700, 703 (7th Cir. 2010). Ruth, 966 F.3d at
652, 654. Because Hudson was on the books when Cherry was
sentenced, it’s unlikely that an objection from trial counsel
would have produced a different outcome.
Cherry’s related theory that the Supreme Court might
have granted his petition for certiorari and agreed with our
sister circuits’ interpretation of § 4B1.2 is even more unlikely:
A few years after Cherry’s sentencing, the Supreme Court de-
nied a petition for certiorari presenting this very question.
Guerrant v. United States, 142 S. Ct. 640 (2022). So no matter
how he slices it, Cherry cannot demonstrate prejudice result-
ing from trial counsel’s failure to object to the § 4B1.1 career-
offender enhancement.
C. Agent Brazao’s Testimony
The claim premised on Agent Brazao’s redirect examina-
tion testimony is also meritless. Cherry contends that his trial
counsel should have objected to the testimony recounting
what the confidential informant told the agents about Cherry
and their prior relationship. He says there were two grounds
to do so. The first is the Confrontation Clause, which guaran-
tees criminal defendants an opportunity to confront and
cross-examine the witnesses against them. U.S. CONST.
No. 21-2231 19
amend. VI; Samia v. United States, 599 U.S. 635, 643 (2023). The
second is Rule 403 of the Federal Rules of Evidence, which
authorizes a district judge to exclude testimony if its proba-
tive value is “substantially outweighed” by the risk of “unfair
prejudice” to the defendant. Cherry likewise faults his appel-
late counsel for failing to raise both issues on appeal.
Even if we assume that trial and appellate counsel per-
formed deficiently by failing to raise these challenges, Cherry
hasn’t proven that the admission of this testimony prejudiced
him. 5 In other words, he hasn’t demonstrated a reasonable
probability of an acquittal had this limited portion of Agent
Brazao’s redirect examination been excluded.
Nor could he. The judge gave a limiting instruction in-
forming the jury to consider this testimony—including the in-
formant’s out-of-court statements—“only for the purpose of
explaining the actions of the agents.” The jury was forbidden,
in other words, to use the informant’s description of Cherry
as proof of his guilt. Absent evidence to the contrary, we pre-
sume that the jury followed this instruction. United States v.
Garcia, 81 F.4th 691, 698 (7th Cir. 2023). There is no contrary
evidence here.
Setting aside the presumption about limiting instructions,
the government’s evidence against Cherry was overwhelm-
ing, and the defense theory was at best highly implausible.
Several agents testified about the heroin recovered from the
black satchel in his Mercedes SUV. Another recounted
Cherry’s postarrest interview in which he admitted to pos-
sessing the heroin with the plan of exchanging it for cocaine.
5 There is accordingly no need for us to address the government’s argu-
ment that Cherry forfeited this claim by omitting it from his § 2255 motion.
20 No. 21-2231
And Cherry’s alternative theory—that the heroin actually had
been found in the informant’s car—was farfetched and en-
tirely speculative. Put simply, the informant’s description of
Cherry was insignificant as compared to the mountain of evi-
dence against him. There is no probability, let alone a reason-
able one, that a challenge to Agent Brazao’s testimony would
have produced a different result either at trial or on appeal.
In short, counsel’s failure to object to the § 841(b)(1) statu-
tory sentencing enhancement entitles Cherry to a new sen-
tence, but his conviction is sound. We accordingly AFFIRM the
judgment in part and REVERSE it in part, VACATE Cherry’s sen-
tence, and REMAND for resentencing.