Otis Elion v. United States

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In the

    United States Court of Appeals
                 For the Seventh Circuit
                     ____________________
No. 24-3014
OTIS R. ELION,
                                                Petitioner-Appellant,
                                 v.

UNITED STATES OF AMERICA,
                                               Respondent-Appellee.
                     ____________________

         Appeal from the United States District Court for the
                     Southern District of Illinois.
           No. 3:17-cv-01349-JPG — J. Phil Gilbert, Judge.
                     ____________________

    ARGUED MAY 22, 2025 — DECIDED SEPTEMBER 24, 2025
                ____________________

   Before BRENNAN, SCUDDER, and KIRSCH, Circuit Judges.
    BRENNAN, Circuit Judge. Otis Elion pleaded guilty to dis-
tributing methamphetamine in 2017. The federal district court
imposed a lengthy sentence for being a “career offender.” U.S.
SENT’G GUIDELINES MANUAL § 4B1.1(a). Elion’s attorney did
not object, because after researching whether his prior convic-
tions qualified as predicate offenses, she concluded that chal-
lenging that sentencing enhancement would fail.
2                                                   No. 24-3014

    In a federal habeas petition, Elion argued his attorney’s
failure to object was deficient and prejudicial, amounting to
ineffective assistance of counsel under Strickland v. Washing-
ton,
466 U.S. 668
(1984). In Elion v. United States (Elion I), we
ruled that he was prejudiced and remanded for the district
court to examine his attorney’s performance under Strickland
in the first instance.
76 F.4th 620, 635
(7th Cir. 2023).
    This successive appeal concerns whether his attorney per-
formed deficiently. We conclude she did not. She identified
and researched the correct issues and properly applied the
categorical approach. Her failure to reach the correct legal
conclusion does not alone establish deficient performance. At
the time of Elion’s sentencing, both her conclusion and overall
performance were reasonable, so we affirm the district court.
                        I. Background
    A. Divisibility Analysis
    A federal defendant with two or more prior state convic-
tions for a “controlled substance offense” may receive a
longer sentence under U.S.S.G. § 4B1.1(a). In this case, deter-
mining whether a state conviction counts as a “controlled sub-
stance offense” requires applying the categorical approach.
Elion I,
76 F.4th at 625
. Under that approach, the elements of
the state statute of conviction are compared to the federal def-
inition of “controlled substance offense.”
Id.
The state statute
triggers the enhancement “only if its statutory elements are
defined in such a way that all possible violations of the stat-
ute, however committed, would fall within Congress’s chosen
federal benchmark.” United States v. Liestman,
97 F.4th 1054
,
1056–57 (7th Cir. 2024) (en banc).
No. 24-3014                                                      3

    But if the state statute’s elements are broader than the
Guideline’s definition, the court then decides whether the
statute is divisible. Elion I,
76 F.4th at 626
. A divisible statute
creates multiple crimes with alternative elements; an indivisi-
ble statute creates a single crime with “a single (or ‘indivisi-
ble’) set of elements.” Mathis v. United States,
579 U.S. 500
,
504–05 (2016); see also United States v. Edwards,
836 F.3d 831,
833
(7th Cir. 2016) (“The Supreme Court [in Mathis] recently
clarified that a statute is considered divisible only if it creates
multiple offenses by setting forth alternative elements.”).
Courts employ different tools to ascertain whether a statute is
divisible. Caselaw and textual evidence are examined first.
Elion I,
76 F.4th at 630
. If the answer is still unclear, a court
inspects the defendant’s record documents, like an indict-
ment or jury instructions, and “the record would then reveal
what the prosecutor has to (and does not have to) demon-
strate to prevail.” Mathis, 579 U.S. at 518–19. If indeterminacy
remains, the statute is treated as indivisible. Elion I,
76 F.4th
at 634
; Taylor v. United States,
495 U.S. 575, 602
(1990). “[C]lear
signals” are required to “convince us to a certainty that the
elements are correct and support divisibility before imposing
additional federal consequences for those state convictions.”
Najera-Rodriguez v. Barr,
926 F.3d 343, 356
(7th Cir. 2019) (cit-
ing Taylor,
495 U.S. at 602
); see also Elion I,
76 F.4th at 635
(same).
    If a statute is divisible, the “modified categorical
approach” requires a court to “scrutinize certain record doc-
uments to determine what crime, with what elements, the de-
fendant was convicted of.” Elion I,
76 F.4th at 626
(citation
modified) (quoting Mathis, 579 U.S. at 505–06). If those ele-
ments meet the Guideline’s definition, then the Guideline ap-
plies, and the defendant can receive a longer sentence.
4                                                         No. 24-3014

    B. Facts
    Against this backdrop, we consider Elion’s case. The facts
are relayed in more detail in Elion I,
76 F.4th at 620
. Elion
pleaded guilty to three counts of distributing methampheta-
mine.
21 U.S.C. § 841
(a)(1), (b)(1)(C). With several prior con-
victions, he may have been eligible for a longer sentence as a
“career offender” under § 4B1.1(a). His eligibility turned on
whether he had twice committed a “controlled substance of-
fense.” Id. A “controlled substance offense” is defined as a
federal or state offense that “prohibits the manufacture, im-
port, export, distribution, or dispensing of a controlled sub-
stance (or a counterfeit substance)” or possession with intent
to engage in those actions, punishable by imprisonment for a
term exceeding one year. Id.; § 4B1.2(b).
    Three of Elion’s convictions 1 ostensibly qualified as “con-
trolled substance offense[s].” Elion I, 625 F.4th at 624. Most re-
cent was a 2006 federal conviction for distribution of a cocaine
base.
21 U.S.C. § 841
(a)(1), (b)(1)(C). Before that was a 2000
conviction for unlawful delivery of a look-alike substance. 720
ILCS 570/404(b) (“§ 404(b)”). The oldest conviction was in
1999 for unlawful delivery of a look-alike substance within
1,000 feet of public housing property. 720 ILCS 570/407(b)(3)
(“§ 407(b)(3)”). This is a penalty statute, “elevating sanctions
for offenders who commit enumerated offenses in certain lo-
cations.” Elion I, 76 F.4th at 626–27 (citation modified). The


    1 Throughout this litigation, Elion’s three charges have been labeled

as convictions dated 1999, 2000, and 2006. Those are the years of the of-
fenses, though, not the convictions, which occurred in 2000, 2003, and
2007, respectively. To avoid confusion, we continue to use the years of
1999, 2000, and 2006. Elion I,
76 F.4th at 624
n.2.
No. 24-3014                                                    5

penalty statute, § 407(b)(3), uses § 404(b)—the same statute as
his 2000 conviction—as its underlying offense.
    The Probation Office concluded that those convictions ren-
dered Elion eligible as a career offender under § 4B1.1. Elion I,
76 F.4th at 623
. His attorney, Judith Kuenneke, also researched
this issue. She reached the same conclusion, so she did not
object to the application of the enhancement at Elion’s sen-
tencing.
Id. at 624
. Instead, she argued Elion’s health and life
circumstances justified a mitigated sentence. The district
court sentenced Elion as a “career offender” to 167 months
imprisonment.
    After Elion’s sentencing, he petitioned for federal habeas
relief.
28 U.S.C. § 2255
. To him, neither his 1999 nor his 2000
state convictions were “controlled substance offense[s].”
Kuenneke’s failure to make that argument therefore violated
his right to effective assistance of counsel under the Sixth
Amendment. The district court disagreed.
    We reversed. Elion I,
76 F.4th at 635
. Using the modified
categorical approach, we “examine[d] the fit between”
§ 404(b) and Guideline § 4B1.1(a). Id. at 626–27. First, § 404(b)
uses the term “look-alike” but the Guideline uses “counterfeit
substance.” Id. Though superficially synonymous, these
terms could be different because the definition of “counter-
feit” may require an intent to deceive, while “look-alike” may
not. Id. at 628. Kuenneke, by contrast, had concluded that
“counterfeit” and “look-alike” were a categorical match. We
ultimately passed on the question. Id.
    There was another mismatch between the two terms:
§ 404(b) punished “advertising” a look-alike substance, yet
the Guideline did not. Id. That meant § 404(b) “punishes a
6                                                  No. 24-3014

broader range of conduct” than the Guideline. Id. at 630. Thus,
§ 404(b) could not serve as a predicate to § 4B1.1(a) unless it
was divisible. Id.
    We concluded that § 404(b) was indivisible. After consult-
ing state and federal caselaw, that statute’s text, documents
from Elion’s conviction, and applicable jury instructions, we
could not “conclusively determine” whether the statute was
divisible. Id. at 630–34. That uncertainty meant Guideline
§ 4B1.1 should not apply to Elion. Id. at 634 (“[W]e cannot sat-
isfy ‘Taylor’s demand for certainty.’”). This conclusion dif-
fered from Kuenneke’s, as she believed § 404(b) was divisible.
Elion thus was prejudiced by Kuenneke’s failure to object,
meeting one of Strickland’s two prongs. This case was re-
manded “so the district court may examine Strickland’s defi-
cient performance prong in the first instance.” Id. at 635.
    The district court held an evidentiary hearing. Kuenneke
testified to her approach, research, and analysis about
whether there was a basis to challenge Elion’s career-offender
designation. She also conceded there were mistakes in an af-
fidavit she had filed previously with the court in response to
Elion’s habeas petition.
     In a meticulous, lengthy opinion, the district court con-
cluded that Kuenneke did not perform deficiently. Elion v.
United States, No. 3:17-cv-01349-JPG,
2024 WL 4527803
(S.D.
Ill. Oct. 17, 2024). The court made several findings: Kuenneke
had identified the correct statute and applied the modified
categorical approach correctly. She researched the many
issues and did not rely unduly on out-of-circuit caselaw. Fi-
nally, Kuenneke also mistakenly wrote down the wrong stat-
ute in her affidavit, but she used the appropriate statute in her
analysis.
No. 24-3014                                                             7

   The district court then analyzed her performance. She had
taken “all appropriate precautions, performed extensive re-
search, used all the avenues at her disposal, and exhausted all
available tools.”
Id. at *30
(citation modified). And “[w]hile
Kuenneke was ultimately incorrect—her conclusion was
based on a reasonable, alternative interpretation based on her
professional judgment, informed by research and decades of
experience.”
Id.
The district court concluded her performance
was better than that of the attorney in Bridges v. United States,
991 F.3d 793
(7th Cir. 2021), a case we suggested could assist
the court. Elion I,
76 F. 4th at 635
.
   Elion appeals. 2 We review factual findings for clear error
and legal conclusions de novo. Pettis v. United States,
129 F.4th
1057, 1062
(7th Cir. 2025).
                II. The District Court’s Findings
   We start with Elion’s challenge to the district court’s find-
ings of fact.
    After Elion filed his habeas petition, the district court al-
lowed Kuenneke to respond to his claim of ineffective assis-
tance of counsel. She did so in an affidavit. That document
describes Kuenneke’s discussions with Elion and her legal
analysis about his career offender status. Relevant here, the
affidavit stated that § 407(b)(3) “was subject to review pursu-
ant to the modified categorical approach.” But because
§ 407(b)(3) is an enhancement statute, it should not have been
used for the categorial approach. Rather, the underlying of-
fense, § 404(b), was the correct statute to apply. See Elion I, 76

   2 The court thanks Kimberly J. Broecker, Esq., and Megan R. Izzo, Esq.,

of Williams & Connolly LLP for providing exceptional assistance in this
complicated and time-intensive case.
8                                                    No. 24-3014

F.4th at 626–27. The categorical approach requires identifying
elements of a crime, and penalty statutes do not list those ele-
ments. Kuenneke also mistakenly attached a copy of
§ 407(b)(3) to her affidavit.
   At the post-remand evidentiary hearing, Kuenneke testi-
fied she reviewed § 404(b), not § 407(b)(3), but mistakenly
wrote down § 407(b)(3). Beyond that, she “couldn’t explain”
how the error occurred.
    The district court found Kuenneke testified truthfully. It
reverse-engineered how the mistake could have happened,
relying on contextual clues in the affidavit. The court found
no reason why she would lie about her performance, particu-
larly when that falsehood could draw scrutiny and possible
perjury charges. Kuenneke had even offered to show her
notes to the court in camera, which the court concluded but-
tressed her truthfulness.
    Understandably, Elion asks us to discount the district
court’s findings of fact. He argues we should rely on
Kuenneke’s affidavit rather than credit her testimony at the
hearing. But the district court’s factual findings were in part
grounded in a credibility determination. In other words, to
believe Kuenneke mistakenly wrote down the wrong statute
hinges on her truthfulness, which is “fundamentally an issue
of credibility.” Elion,
2024 WL 4527803
, at *21.
    A court of review may disregard a credibility determina-
tion only if it is “completely without foundation.” United
States v. Clark,
134 F.4th 480
, 482 (7th Cir. 2025) (quoting
United States v. Sands,
815 F.3d 1057, 1061
(7th Cir. 2015)). This
deferential standard of appellate review exists because trial
courts have “the best opportunity to observe the verbal and
No. 24-3014                                                    9

nonverbal behavior of the witnesses” by “focusing on the sub-
ject’s reactions and responses to the interrogatories, their fa-
cial expressions, attitudes, tone of voice, eye contact, posture
and body movements, as well as confused or nervous speech
patterns in contrast with merely looking at the cold pages of
an appellate record.” United States v. Eddy,
8 F.3d 577
, 582–83
(7th Cir. 1993) (citation modified). As a result, credibility de-
terminations can virtually never be clear error. United States v.
Harris,
124 F.4th 1088, 1092
(7th Cir. 2025).
     The district court made a credibility determination when
it found Kuenneke truthful that she made a mistake. It noted
her lengthy experience as a defense attorney and that she was
highly unlikely to lie. Also, the court explained why, despite
Kuenneke’s mistakes in her affidavit, she performed the
categorical approach by analyzing § 404(b). For example,
§ 407(b)(3) references § 404(b), thus “even if Kuenneke put the
cart before the horse and jumped straight to the divisibility
analysis,      even     if   she      treated    Elion’s Section
407(b)(3) conviction as a fictitious discrete offense, she
would still need to evaluate Section 404(b) as an ‘element’ of
a Section 407(b)(3) violation.” In the affidavit, a citation to
United States v. Hinkle,
832 F.3d 569
, 576–77 (5th Cir. 2016) (a
Texas controlled-substance statute is indivisible and not a
categorical match with the Guideline), along with other
textual clues, was “further evidence that she analyzed the
correct statute.”
    Elion counters that the district court made no specific fac-
tual findings about Kuenneke’s demeanor on the stand, so we
should disregard its findings, as in Ray v. Clements,
700 F.3d
993, 1013
(7th Cir. 2012). That overreads Ray’s holding. There,
this court stated: “the district court made no finding
10                                                    No. 24-3014

concerning Ray’s demeanor or presentation, and instead
based its ‘credibility’ finding on nothing more than a string of
speculative doubts, none of which were based on any compe-
tent contradictory evidence presented by the state.”
Id.
Ray
thus does not grant free rein to appellate courts to disregard
credibility determinations when a district court does not
opine on a witness’s demeanor. And in contrast to Ray, the
district court here gave reasons why it found Kuenneke truth-
ful: her experience and lack of motive to lie along with textual
evidence in the affidavit.
    To conclude, we affirm the district court’s factual findings.
Kuenneke mistakenly wrote down and attached the wrong
statute. But she identified § 404(b) as the correct statute for the
categorical approach and noticed the potential mismatches
between that statute and the Guideline. She performed a di-
visibility analysis, researched the relevant issues, and em-
ployed the modified categorical approach.
                  III. Deficient Performance
    This court held in Elion I that Kuenneke’s performance
prejudiced Elion.
76 F.4th at 635
. Whether her performance
was deficient turns on whether Kuenneke’s “representation
fell below an objective standard of reasonableness.” Strick-
land,
466 U.S. at 688
. Counsel’s performance need not be per-
fect to be objectively reasonable. “Criminal defendants have a
right to a competent lawyer, but not to Clarence Darrow.”
United States v. Rezin,
322 F.3d 443
, 446–47 (7th Cir. 2003), over-
ruled on other grounds by Lockhart v. United States,
577 U.S. 347
(2016). And courts must make “every effort … to eliminate the
distorting effects of hindsight.” Strickland,
466 U.S. at 689
.
No. 24-3014                                                   11

    First, we discuss whether Kuenneke’s incorrect legal con-
clusion alone makes her performance deficient. Next, we con-
sider whether our caselaw foreshadowed our conclusion in
Elion I. We then evaluate whether Kuenneke should have at
least made the categorical approach argument. Last, we ana-
lyze her performance as a whole.
   A. Mistake of Law
    The district court concluded that Kuenneke’s choice not to
challenge the sentencing enhancement was not strategic. Ra-
ther, she opted not to object because she had reached an in-
correct legal conclusion that § 404(b) was divisible (even
though this court had not yet determined that § 404(b) was
indivisible until Elion I). She then chose not to advance the
claim, as she deemed it not viable.
   Elion tells us that our caselaw establishes that if an attor-
ney fails to make a winning argument solely because she
reached a legally incorrect conclusion, it is deficient perfor-
mance. For support, Elion points to Cates v. United States,
882
F.3d 731, 736
(7th Cir. 2018), and Bridges,
991 F.3d at 800
.
    But that is emphatically not what our caselaw holds. We
have repeatedly stated that counsel need not forecast changes
in the law. “Defense attorneys, it is true, are generally not
obliged to anticipate changes in the law,” and “it is not
enough to show that a challenge to the career offender en-
hancement should have prevailed.” Bridges,
991 F.3d at 802,
804
; Resnick v. United States,
7 F.4th 611, 623
(7th Cir. 2021)
(“[O]ur case law provides that failure to object to an issue that
is not settled law within the circuit is not unreasonable by de-
fense counsel.”); see also Scott v. Hepp,
62 F.4th 343, 348
(7th
Cir. 2023) (AEDPA case but discussing Strickland’s principle
12                                                   No. 24-3014

that “a failure to argue a point of unsettled law, not foreshad-
owed by existing case law, ‘is not enough by itself to demon-
strate deficient performance’” (quoting Minnick v. Winkleski,
15 F.4th 460, 470
(7th Cir. 2023))). As these cases make clear, a
defense attorney’s choice not to make a potentially meritori-
ous argument is not automatically deficient performance,
even if it stems solely from a legal error.
    Nor can Elion’s reading of our caselaw be reconciled with
Strickland, which instructs that the “proper measure of
attorney performance remains simply reasonableness under
prevailing professional norms.”
466 U.S. at 688
. Strickland nec-
essarily permits mistakes that are reasonable. Only when the
defense attorney’s error is so appalling that he can no longer
be considered “counsel” for his client is his performance
deemed deficient. Harrington v. Richter,
562 U.S. 86, 104
(2011).
Strickland does not demand clairvoyance. “[L]aw is no exact
science … . The giving of legal advice that later is proven to
be incorrect, therefore, does not necessarily fall below the ob-
jective standard of reasonableness.” Smith v. Singletary,
170
F.3d 1051, 1054
(11th Cir. 1999). We recognized this point
when we said, “[c]riminal defendants have a right to a com-
petent lawyer, but not to Clarence Darrow.” Rezin, 322 F.3d at
446–47. Elion’s proffered rule cannot be reconciled with these
principles.
    To be sure, we stated in Cates, “a mistake of law is deficient
performance.”
882 F.3d at 736
. But that statement must be
read in context. First, counsel there did not object to a jury in-
struction that “plainly misstated” the law by “flatly contra-
dict[ing]” the statutory text.
Id. at 737
. So, as the government
correctly points out, the error there was egregious. And the
full quote from Cates shows that its holding concerns jury
No. 24-3014                                                     13

instructions: “There is no conceivable strategic reason for a
defense lawyer to forgo a challenge to a prejudicial jury in-
struction.”
Id. at 736
. Since Cates, this court has understood
that case’s holding to apply to jury instructions. See Powell v.
Fuchs,
4 F.4th 541
, 547–48 (7th Cir. 2021) (“When a jury in-
struction so badly misstates the law and that error relaxes the
government’s burden of proof, this court held that there can
be no conceivable strategic reason for counsel not to object.”
(citing Cates,
882 F.3d at 736
)). Second, Cates cited Vineyard v.
United States,
804 F.3d 1218, 1225
(7th Cir. 2015), which stated
that a “misunderstanding of law or fact, however, can amount
to ineffective assistance.”
Id.
(emphasis added). So, Vineyard
does not support reading Cates to hold that a misunderstand-
ing of law always amounts to ineffective assistance.
    Elion also claims a “mistake of law” is when counsel mis-
understands the law. That position lacks a limiting principle.
If an attorney declines to make an argument that no court has
accepted and no other attorney has made, yet which later suc-
ceeds, it is doubtful the attorney’s omission was unreasonable
under “[p]revailing norms of practice.” Strickland,
466 U.S. at
688
. Yet under Elion’s definition, the attorney is deficient.
    In addition, under Elion’s rule, defense attorneys would
have to raise all possible arguments, even wrong ones. Other-
wise, many years later, counsel could be judged deficient for
possibly misunderstanding the law. But “trial counsel may
undermine the credibility of the defense of his client if he
simply presents the court with a barrage of attacks.” Lickers v.
United States,
98 F.4th 847, 857
(7th Cir. 2024) (quoting Goins
v. Lane,
787 F.2d 248, 254
(7th Cir. 1986)). Elion’s rule therefore
runs counter to the interests of criminal defendants.
14                                                   No. 24-3014

   An attorney’s mistake of law is not always deficient per-
formance under Strickland. For that reason, Kuenneke’s deci-
sion not to raise a potentially meritorious argument—even
though not done strategically—is not automatically deficient
performance.
     B. Foreshadowing Exception
    Although a single mistake of law is not always deficient
performance, there is a narrow exception in the categorical
approach context. This occurs when an attorney fails to
recognize that our caselaw foreshadows an argument that
later succeeds. We outline the law on this exception, but we
reject Elion’s arguments that he falls within it.
        1. This court’s caselaw
    Strickland tells courts to assess attorney performance based
on “prevailing professional norms.”
466 U.S. at 688
. A single
legal error rarely demonstrates deficient performance. Richter,
562 U.S. at 111
. This includes failing to “anticipate changes in
the law.” Bridges,
991 F.3d at 804
. But a narrow exception ex-
ists for solitary errors that are “sufficiently egregious and prej-
udicial.” Richter,
562 U.S. at 111
(quoting Murray v. Carrier,
477
U.S. 478, 496
(1986)). “An attorney’s ignorance of a point of
law that is fundamental to his case combined with his failure
to perform basic research on that point is a quintessential ex-
ample of unreasonable performance under Strickland.” Hinton
v. Alabama,
571 U.S. 263, 274
(2014).
   Our caselaw has applied this exception to an attorney’s
performance of the categorical approach. For example, in
Bridges, the defendant was indicted for Hobbs Act robbery
and later pleaded guilty.
991 F.3d at 797
. As part of his guilty
plea, he agreed that his crime of conviction was a “crime of
No. 24-3014                                                   15

violence” under the Guideline’s career-offender enhance-
ment.
Id.
His attorney failed to object to that label at sentenc-
ing.
Id.
at 797–98. He later sought postconviction relief, alleg-
ing his attorney was ineffective for failing to object to the ca-
reer offender designation.
Id. at 799
. Had counsel done “min-
imal research,” he would have “uncovered a Tenth Circuit de-
cision squarely holding that Hobbs Act robbery was no longer
a crime of violence,” although the Seventh Circuit had yet to
reach that holding.
Id.
at 797–98.
    Though “defense attorneys … are generally not obliged to
anticipate changes in the law,” attorneys can still be deficient
if the argument was “sufficiently foreshadowed.”
Id. at 804
.
Thus, even though this court had not reached such a holding,
out-of-circuit caselaw provided a clear path for Bridges’s at-
torney.
Id. at 805
. Nor was such an argument obscure, as mak-
ing Guidelines arguments is a “core competency” of federal
defense counsel.
Id. at 804
(citation modified). The case was
remanded for an evidentiary hearing to determine whether
“defense counsel had a reasonable sentencing strategy.”
Id. at
807
.
    Following Bridges was Harris v. United States,
13 F.4th 623,
625
(7th Cir. 2021). There, the defendant had several prior
state drug convictions.
Id.
When he pleaded guilty to a federal
drug offense, his attorney failed to argue whether those prior
drug convictions counted as “felony drug offense[s]” under a
sentencing enhancement provision.
Id.
We concluded that
counsel “should have known about a possible categorical
challenge.”
Id. at 629
. This was true even though the argument
had not yet been addressed, as at the time of sentencing “at
least one court had considered the issue.”
Id.
at 629–30. What
is more, the categorical approach framework was well
16                                                  No. 24-3014

established, and the “analysis called for” was not complex—
counsel simply “had to compare the plain language of stat-
utes.”
Id. at 630
. But given counsel’s options at the time, his
performance was not deficient. The “defense essentially had
a bird in the hand—the plea offer with a set 20-year sen-
tence—with a possibility of two in the bush—the novel chal-
lenge to the predicate offenses with the risk of a mandatory
life sentence.”
Id. at 631
. Thus, it was “objectively reasonable”
for counsel not to raise the categorical challenge and instead
accept the plea deal.
Id.
Harris and Bridges each recognize this “failure to fore-
shadow” exception. When “case law sufficiently foreshad-
owed [an] argument,” the attorney “could be deemed to have
been deficient” for not advancing it. Bridges,
991 F.3d at 804
.
But the definition of “foreshadowing” has its limits. After all,
an attorney is constitutionally ineffective only if his errors are
“so serious” that he no longer functions as “counsel.” Strick-
land,
466 U.S. at 687
. To “eliminate the distorting effects of
hindsight,” courts put themselves “in defense counsel’s shoes
at the time of the challenged acts or omissions” to assess his
performance. Lickers,
98 F.4th at 857
(quoting Strickland,
466
U.S. at 689
). Existing decisions therefore must “sufficiently”
foreshadow the argument. Bridges,
991 F.3d at 804
; Harris,
13
F.4th at 629
. We hold that a “sufficiently foreshadowed” argu-
ment is one that no reasonable attorney could fail to foresee.
Kimbrough v. United States,
71 F.4th 468, 472
(6th Cir. 2023).
    A reasonable attorney could, for example, be expected to
raise a foreshadowed argument when courts in the jurisdic-
tion expressly predicted the change. Chase v. MaCauley,
971
F.3d 582, 594
(6th Cir. 2020) (“[J]udges on the Michigan Court
of Appeals panel … had clearly and forcefully detailed
No. 24-3014                                                   17

why Alleyne rendered Michigan’s sentencing scheme uncon-
stitutional.”). But persistent uncertainties in an area of law
might mean it was not possible to foresee a particular change.
    This exception for failing to raise a foreshadowed claim is
narrow and rarely applies. This is because “defense attor-
neys … are generally not obliged to anticipate changes in the
law.” Bridges,
991 F.3d at 804
; see also Harris,
13 F.4th at 629
(stating that the “reasonableness of counsel’s performance
must be assessed in the context of the law at the time” (cita-
tion modified)). Infrequent application of this exception en-
sures that courts do not allow hindsight to color judgment of
an attorney’s performance but rather evaluate the perfor-
mance using “prevailing professional norms.” Strickland,
466
U.S. at 689
.
   These principles in tow, we move to Elion’s case.
       2. That caselaw applied to Elion
    In 2017 this circuit had yet to decide the legal issue in El-
ion’s case. The question therefore is whether Elion I’s conclu-
sion was “sufficiently” foreshadowed by existing caselaw,
such that Kuenneke’s failure to advance the argument is defi-
cient performance.
    Elion first claims that Kuenneke did not need to recognize
a foreshadowed argument. Instead, she should have con-
cluded that “delivery” and “distribute” in § 404(b) are ambig-
uous, not synonymous. At the time, Taylor established that
courts must be certain when imposing an enhanced sentence
under the categorical approach. See Elion, 76 F.4th at 634–35
(stating that a “lack of clear signals” compelled a conclusion
that the statute was indivisible and citing Mathis,
579 U.S. at
18
No. 24-3014

519). So, to Elion, Kuenneke should have at least raised an ar-
gument that Taylor’s demand for certainty had not been met.
    True, before Elion’s sentencing Taylor did demand cer-
tainty. See Shepard v. United States,
544 U.S. 13, 21
(2005). But
Strickland tells us to put “ourselves in defense counsel’s shoes
at the time of the challenged acts or omissions.” Lickers,
98
F.4th at 857
. Considering Kuenneke’s position at the time, Tay-
lor’s principle would have been of little use to her. For her to
benefit from it, she needed concrete applications of that prin-
ciple that were similar to Elion’s case. That is particularly true
because “certainty” is a standard, not a rule. Reasonable
minds can disagree as to its application; what one finds cer-
tain, another finds ambiguous. Thus, Kuenneke is not defi-
cient for failing to offer the categorical approach argument
just because Taylor’s certainty principle was established in
2017.
    This court in 2017 had yet to answer two key questions for
Kuenneke’s analysis. First up is whether “look-alike” was
synonymous with “counterfeit.” In United States v. Hudson,
this court had held that Indiana’s statute using “look-alike”
was a categorical match with “counterfeit” under the Guide-
line.
618 F.3d 700
(7th Cir. 2010). And in United States v. Rob-
ertson, the Eighth Circuit had held that Illinois’s definition of
“look-alike” was also a categorical match with “counterfeit”
under the Guideline.
474 F.3d 538
(8th Cir. 2007). So, existing
caselaw suggested Elion’s argument would not succeed.
   Nor had this court answered a second question on the ad-
vertising mismatch. Kuenneke, however, researched the issue
and located United States v. Hinkle,
832 F.3d at 569
. But Hinkle
was of little help because it was specific to a Texas statute, and
the categorical approach can turn on a state’s view of its law.
No. 24-3014                                                   19

See, e.g., United States v. Franklin,
895 F.3d 954, 958
(7th Cir.
2018) (per curiam) (differentiating between Wisconsin’s and
Iowa’s burglary statutes). In sum, existing caselaw either did
not apply or strongly disfavored Elion’s categorical approach
argument.
    At issue is whether a reasonable attorney could have failed
to foresee the conclusion in Elion I. As explained, an attorney
can be deficient for not raising a foreshadowed argument
when obvious caselaw is missed. Harris,
13 F.4th at 629
;
Bridges,
991 F.3d at 805
. But if the attorney does locate that
obvious caselaw, yet that precedent strongly disfavors the cli-
ent’s argument, no reasonable attorney would foresee this
court holding the opposite. That is what happened here. Rob-
ertson analyzed “the same two terms now at issue” but
reached a conclusion that cut against Elion. Elion I,
76 F.4th at
628
. Hudson also cast doubt on whether Elion’s argument
would succeed. And no court had answered the advertising
mismatch, except Hinkle, which turned on the particulars of
Texas law and thus did not aid Elion’s case. For these reasons,
when Elion was sentenced, a reasonable attorney would not
foresee Elion I’s conclusion. See United States v. Carthorne,
878
F.3d 458, 466
(4th Cir. 2017) (“[C]ounsel may be constitution-
ally required to object when there is relevant authority
strongly suggesting that a sentencing enhancement is not
proper.”). So, Kuenneke did not perform deficiently by failing
to raise that ultimately successful argument.
    Contrast Kuenneke’s performance with that of the lawyers
in Bridges and Harris—two cases falling under the “foreshad-
owing exception.” Start with Bridges. The chief difference is
the depth and quality of the legal research. In Bridges, the at-
torney missed a “noteworthy published opinion,” which
20                                                 No. 24-3014

answered the issue in his case.
991 F.3d at 805
. “With modern
methods of legal research, it would not have taken long in
2018 for counsel to have found the Tenth Circuit decision
holding that Hobbs Act robbery is not a crime of violence un-
der the 2016 guideline amendment.”
Id.
Nor was that the only
case discussing the issue. “Counsel checking cita-
tions … would have also found the Fourth Circuit’s opinion
in United States v. McCollum,
885 F.3d 300
(4th Cir. 2018), is-
sued just one month before Bridges signed his plea agree-
ment.” Id. at 806. Because caselaw offered a clear avenue of
relief, and reasonable counsel would understand and recog-
nize the categorical approach, counsel may have been defi-
cient for not raising the argument.
    Kuenneke, by contrast, did the necessary work. She re-
searched the categorical approach arguments, found the ap-
plicable caselaw, and analogized that precedent to Elion’s
case. When the caselaw provided no answer, she used statu-
tory interpretation and relied on her extensive experience.
Kuenneke just reached a different conclusion than Elion I—a
conclusion on which reasonable minds could disagree.
    Kuenneke’s performance was also considerably better
than that of the attorney in Harris. There, the attorney “should
have known about a possible categorical challenge.”
13 F.4th
at 629
. A circuit court had applied the categorical approach to
the “federal ‘felony drug offense’ definition,” and the issue
was an easy one to spot.
Id.
at 629–30. But here, Kuenneke rec-
ognized the categorical approach issue and thoroughly exam-
ined its viability.
   Elion argues that focusing solely on the amount of legal
research treats Strickland as a “mere billable-hours require-
ment,” leading to absurd results: An attorney who
No. 24-3014                                                                21

exhaustively researches an issue but misunderstands a core
holding would not be deficient. We disagree. How thoroughly
an attorney researches an issue can reflect the quality of that
attorney’s performance. Yet the evaluation entails many other
factors, such as the difficulty of the legal question presented.
An attorney’s error is less justifiable when the categorical ap-
proach analysis is “not complex.” Harris,
13 F.4th at 630
. So,
the opposite is also true—when that analysis is complex, as
here, an attorney’s legal error is more reasonable. 3 And as
Bridges emphasized, Strickland’s performance test also consid-
ers the strength of available alternative arguments. 991 F.3d at
807–08. Thus, our caselaw does not focus only on the attor-
ney’s time spent researching the law.
   Only in rare circumstances will precedent foreshadow a
change in law. “The change must be so obvious that no rea-
sonable jurist or attorney could fail to foresee it.” Kimbrough,
71 F.4th at 472
(citation modified). Elion’s categorical ap-
proach argument was not foreshadowed because existing
caselaw was silent or cut against it. As the district court here
correctly recognized, Kuenneke’s performance is not analo-
gous to that of the attorneys in Bridges and Harris, who should
have foreseen a successful categorical approach argument.




    3 The categorical approach is not always straightforward. “Even a sin-

gle such categorical analysis is an arduous task, requiring a close analysis
of the specific statutory language put at issue.” De Lima v. Sessions,
867
F.3d 260, 268
(1st Cir. 2017). Its complexity has prompted calls for its erad-
ication. United States v. Taylor,
596 U.S. 845
, 867–73 (2022) (Thomas, J.,
dissenting); United States v. Doctor,
842 F.3d 306, 313
(4th Cir. 2016) (Wil-
kinson, J., concurring) (labeling the categorical approach a “protracted
ruse”).
22                                                   No. 24-3014

       3. Coleman and its rule applied to Elion
    Elion also points us to United States v. Coleman,
79 F.4th 822
(7th Cir. 2023), for support. There, defense counsel failed to
challenge whether the defendant’s prior convictions were
convictions for a “felony drug offense.”
Id. at 826
. This court
agreed that a remand was necessary because it was “objec-
tively unreasonable for Coleman’s defense counsel to have
not even considered a categorical challenge.”
Id. at 832
.
   Coleman reached this conclusion via the foreshadowing ex-
ception.
Id. at 831
. The argument Coleman’s attorney failed to
make would have been novel at the time.
Id.
No circuit court
had addressed the question.
Id. at 833
(Easterbrook, J., dissent-
ing). And it would take this court six years after Coleman’s
sentencing to do so.
Id.
(citing United States v. Ruth,
966 F.3d
642
(7th Cir. 2020)). Yet, this court in Coleman held that
caselaw foreshadowed the argument the attorney failed to
make because “the groundwork for such an argument” had
been laid in other cases in different contexts. Id. at 831.
    Coleman extended the holdings of Bridges and Harris. In-
deed, Coleman’s holding can be read so broadly as to be “mis-
aligned with our Strickland jurisprudence.” Neal v. United
States, No. 23-1722,
2025 WL 2553445
, at *5 (7th Cir. 2025). To
illustrate how, consider an example. For a time, the
Confrontation Clause’s promise that the accused has a right
to confront the witnesses against him could be overcome if the
out-of-court statement had an “adequate indicia of reliabil-
ity.” Ohio v. Roberts,
448 U.S. 56
, 65–66 (1980) (citation modi-
fied). The Court, relying largely on historical evidence, then
abandoned that test in Crawford v. Washington to align closer
with the Clause’s original meaning.
541 U.S. 36
, 43–50 (2004).
Taken to its logical limit, this change would mean that every
No. 24-3014                                                   23

federal defender with a Confrontation Clause argument be-
fore Crawford performed deficiently if by failing to argue that
Ohio’s “adequate indicia” test was wrong as an original mat-
ter. One could contend that the “groundwork for such an ar-
gument” was already laid because the historical sources were
accessible, and the focus on text, history, and tradition had
been emphasized in other “contexts.” Cf. Coleman,
79 F.4th at
832
(“[T]he groundwork for such an argument was, at the
very least, foreshadowed by numerous decisions … in other
contexts.”). That is difficult to reconcile with Strickland’s in-
structions that the “proper measure of attorney performance”
is “reasonableness under prevailing professional norms.”
Strickland,
466 U.S. at 688
(emphasis added).
    Rather, the application of Strickland in Coleman must be
read in light of cases such as Hinton and Richter. Those cases
establish that only egregious errors amount to deficient per-
formance. Hinton,
571 U.S. at 274
(“An attorney’s ignorance of
a point of law that is fundamental to his case combined with
his failure to perform basic research on that point is a quintes-
sential example of unreasonable performance under Strick-
land.”); Richter,
562 U.S. at 111
(“And while in some instances
even an isolated error can support an ineffective-assistance
claim if it is sufficiently egregious and prejudicial, it is diffi-
cult to establish ineffective assistance when counsel’s overall
performance indicates active and capable advocacy.” (citation
modified)). Strickland emphasizes that a “fair assessment of
attorney performance requires that every effort be made to
eliminate the distorting effects of hindsight … and to evaluate
the conduct from counsel’s perspective at the time.”
466 U.S.
at 689
. Coleman suggests counsel is deficient any time some
amount of “groundwork” has been previously laid and that
attorney fails to make an unobvious but ultimately successful
24                                                    No. 24-3014

argument. Instead, the test is whether the “groundwork”
sufficiently foreshadows the argument so that no reasonable
attorney would fail to make it. Kimbrough,
71 F.4th at 472
. Cole-
man sits at the outer boundary of that test.
    This case is not analogous to Coleman. There, the attorney
failed even to consider the categorical approach argument.
79
F.4th at 832
. By contrast, Kuenneke considered, researched,
and analyzed that argument. Coleman emphasized that the ar-
gument the attorney failed to make was not complex.
Id.
Not
so here. Kuenneke’s analysis turned on nuanced differences
between the definitions of “counterfeit” and “look alike,” or
whether “distribute” meant “delivery,” questions we called
“complex” and “ambiguous” and that we could not “conclu-
sively determine.” Elion I,
76 F.4th at 628, 634
. So, we conclude
that Elion’s case does not fall into the foreshadowing excep-
tion.
     C. Failure to Argue
    But wait, Elion argues, Kuenneke should have at least
tried to make a categorical approach argument. After all, she
testified that when she began researching Elion’s case, there
was potentially an argument pursuant to Mathis about the cat-
egorical approach.
   For support, Elion relies on Polk County v. Dodson,
454 U.S.
312
(1981). There, the Court stated, “a defense attorney has a
duty to advance all colorable claims and defenses.”
Id. at 323
.
But Polk County considered whether public defenders act “un-
der color of state law.”
Id. at 314
. Polk’s statement is not a rule
changing the effectiveness standard under the Sixth Amend-
ment.
No. 24-3014                                                    25

   Kuenneke did agree “there may have been an argument
pursuant to Mathis.” But that is true for all sorts of challenges;
that does not mean she must raise every one. Counsel has a
duty to raise only sufficiently foreshadowed arguments, not
viable ones. See Bridges,
991 F.3d at 802
(“[I]t is not enough to
show that a challenge to the career offender enhancement
should have prevailed.”); Kimbrough,
71 F.4th at 473
.
    There is a good reason for this rule. Defense attorneys of-
ten have several potential arguments to advance but only lim-
ited resources. Time and effort spent on one argument takes
away from another. So, it is natural for defense attorneys to
shy away from novel, nuanced, or counterintuitive conten-
tions and stick to previously productive arguments.
Kuenneke chose not to offer difficult, counterintuitive reason-
ing—whether “counterfeit” is synonymous with “look-alike”
and whether “distribute” is synonymous with “delivery.” In-
stead, she made mitigating arguments that she had investi-
gated, which she felt had a higher chance of success. In the
end, the court gave Elion a shorter sentence than what the
government requested.
   As well, “there is a tactical reason not to make weak argu-
ments” because “they may distract the court from the strong
arguments and as a result make it less likely to rule in the de-
fendant’s favor.” Rezin,
322 F.3d at 446
. Here, after research,
Kuenneke judged Elion’s categorical approach argument to
not be “a viable objection.” Nor is it an answer to say
Kuenneke should have made the categorical approach argu-
ment in addition to the mitigating arguments. She “cannot be
faulted for eschewing the proverbial kitchen sink and instead
focusing on arguments with better odds.” Lickers,
98 F.4th at
857
. “[T]rial counsel may undermine the credibility of the
26                                                    No. 24-3014

defense of his client if he simply presents the court with a bar-
rage of attacks.”
Id.
(quoting Goins v. Lane,
787 F.2d 248, 254
(7th Cir. 1986)).
    In short, it is not whether counsel could have made an ar-
gument, but whether counsel unprofessionally erred by not
making an argument. Kuenneke’s performance was not defi-
cient solely because she did not offer a potentially valid cate-
gorical approach argument. Cf. Williams v. Lemmon,
557 F.3d
534, 538
(7th Cir. 2009) (per curiam) (An egregious error is “an
omission of something obviously better (in light of what was
known at the time) than the line of defense that counsel pur-
sued.”).
     D. Kuenneke’s Performance as a Whole
    Last, the government correctly points out that Kuenneke’s
performance must be “assessed as a whole; it is the overall
deficient performance, rather than a specific failing, that con-
stitutes the ground for relief.” Peoples v. United States,
403 F.3d
844, 848
(7th Cir. 2005). “While in some instances even an iso-
lated error can support an ineffective-assistance claim, it is
difficult to establish ineffective assistance when counsel’s
overall performance indicates active and capable advocacy.”
Richter,
562 U.S. at 111
(citation modified).
    Elion claims Kuenneke’s performance was worse than that
of the attorney in United States v. Winstead,
890 F.3d 1082
(D.C.
Cir. 2018). There, the defendant’s attorney failed to make a
novel (for that circuit) Guideline argument that five circuits
had already rejected.
Id. at 1089
. The court concluded that
counsel was deficient for not making the argument because
“there was no conceivable tactical reason … for not making
it.”
Id. at 1090
. That was not the only error made by the
No. 24-3014                                                   27

attorney, however. The court was troubled that “Winstead’s
counsel did not put up much opposition at the sentencing
hearing” when he said, “[y]our honor … [m]y client is re-
signed to his fate … . I can only be candid with this court.”
Id.
at 1087–88. By conceding, rather than making an “obvious
[Guideline] legal argument”—“the only serious argument the
defendant had in the entire case”—counsel was deficient.
Id.
at 1090
. So, counsel, judged as a whole, made several mistakes
including an egregious concession.
    Kuenneke, on the other hand, investigated and offered vi-
able mitigation arguments to advocate for a shorter sentence.
She did so after identifying and researching the relevant cate-
gorical approach questions. Kuenneke mistakenly reached a
different conclusion than Elion I, an error mitigated by the nu-
ance and complexity of the analysis. Kuenneke’s performance
as a whole therefore was not deficient.
                        IV. Conclusion
    Kuenneke spotted the issues in Elion’s case, researched
them, and correctly applied the categorical approach. She de-
cided not to offer a categorical approach argument because
she believed the state statute of conviction was divisible. We
later held that statute was indivisible. Kuenneke’s conclusion,
though incorrect and prejudicial to Elion, was not deficient
performance because caselaw did not foreshadow our hold-
ing. So, Kuenneke’s representation of Elion was not ineffec-
tive assistance of counsel.
                                                      AFFIRMED.