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Chicago, Illinois criminal defense lawyer represented defendant charged with a
possession with intent to distribute 50 grams or more of methamphetamine.

Harris was charged in 2016 with possessing with intent to
distribute 50 grams or more of methamphetamine.
See 21 U.S.C. § 841(a)(1) (2010). Because of his prior drug convictions, Harris faced significant sentencing exposure. At the
time, the statutory minimum sentence for this crime was 10
years. Id. § 841(b)(1)(A)(viii) (2010). But under that statute, the
government could enhance the potential sentence by arguing
that two of Harris’s prior convictions were felony drug offenses: an Indiana conviction in 2006 for dealing cocaine,
see IND. CODE § 35-48-4-1(a) (2006), and an Indiana conviction
in 2001 for possessing cocaine, see id. § 35-48-4-6(a) (2001). At
that time, one prior “felony drug offense” increased the mandatory minimum sentence to 20 years, while two required a
life sentence. See 21 U.S.C. § 841(b)(1)(A)(viii) (2010).
To avoid a life sentence, Harris reached an agreement under Federal Rule of Criminal Procedure 11(c)(1)(C) with the
No. 19-3363 3
government to plead guilty and accept a sentence of 20 years’
imprisonment. Pursuant to that deal, the government filed a
notice under 21 U.S.C. § 851 listing only one predicate offense,
the 2006 Indiana conviction for dealing cocaine. At a joint
change-of-plea and sentencing hearing in October 2017, the
district court confirmed that “the basis” for Harris’s plea was
his (and his counsel’s) understanding that he was avoiding a
mandatory life sentence due to the government’s agreement
not to introduce his 2001 Indiana cocaine possession conviction. The court also confirmed that Harris knew he was waiving his right to challenge his conviction and sentence, except
as to ineffective assistance of counsel.
Harris did not appeal. Instead, acting pro se, he timely
moved to vacate his sentence pursuant to § 2255. Harris asserted his counsel had been ineffective “during plea bargaining for the failure to challenge the § 851 enhancement towards
the prior dealing in cocaine case.” In his petition, Harris attempted to explain:
Thomas Brodnick represented me during plea
negotiations. My prior 2006 conviction for dealing in cocaine or narcotic was used to enhance
my sentence under the statute from 10-years to
20-years minimum. This conviction was from
when I was set up to bring someone some drugs
when in fact, I was set up to be robbed. I had to
fight for my life were [sic] I could have died if I
did not defend myself. The State Statute 35-48-
4-1 was used under Indiana state laws and the
case was converted to have me plead guilty to
dealing in cocaine or narcotic and the possession cocaine of [sic] narcotic and dealing in
4 No. 19-3363
cocaine or narcotic was dismissed by the State
for my plea of guilty.
The government read this submission as an argument that
Harris’s counsel should have challenged the sufficiency of the
evidence supporting the 2006 conviction. In reply, Harris
reiterated his initial statements and asserted that his 2006 conviction “is not permissible to be used because of its unconstitutional nature in light of Descamps v. United States, 570 U.S.
254 (2013).”
The district court denied Harris’s § 2255 motion. To that
court, Harris had raised two theories of ineffective assistance:
that his counsel should have (1) challenged the sufficiency of
the evidence underlying his prior state conviction, and (2)
argued that conviction did not qualify as a predicate offense
after Descamps. The first theory failed because a defendant
cannot collaterally attack a state conviction during federal
sentencing unless it was obtained in a proceeding where the
defendant was denied his right to counsel, which Harris did
not allege. See Custis v. United States, 511 U.S. 485, 496–97
(1994). On the second theory, the district court decided that a
Descamps-based argument would have failed at sentencing
because Harris’s 2006 Indiana conviction for dealing cocaine
fell within the definition of a “felony drug offense.” That conviction was based “on conduct relating to narcotic drugs” and
was punishable by a minimum of six years in prison.
Soon after judgment, two legal developments clarified
whether Harris’s prior convictions fit the definition of a “felony drug offense.” First, in United States v. De La Torre,
940 F.3d 938, 952 (7th Cir. 2019), this court held that a different
Indiana drug crime was not a “felony drug offense” because
the state’s definition of the controlled substance involved—
No. 19-3363 5
including, among other terms, its definition of an “isomer”—
applied more broadly than federal law. Less than a year later,
this court decided in United States v. Ruth, 966 F.3d 642, 647,
650 (7th Cir. 2020), that an Illinois conviction for possession
with intent to deliver cocaine was not a “felony drug offense”
because Illinois’s definition of cocaine—like Indiana’s—included optical, positional, and geometric isomers, and therefore was broader than federal law.
Harris requested a certificate of appealability, which this
court granted, as to whether his counsel was ineffective for
failing to argue that his prior conviction did not qualify as a
predicate “felony drug offense” because IND. CODE §§ 35-48-
1-7 and 35-48-2-8(b) (2006) defined cocaine more broadly than
the federal code, 21 U.S.C. §§ 802(17)(C)(D). The parties were
also asked to address whether Harris waived this theory of
ineffectiveness by insufficiently developing it in the district
court.
II
A
Section 2255 provides relief for a federal prisoner if their
sentence “was imposed in violation of the Constitution or
laws of the United States, or [if] the court was without jurisdiction to impose such sentence, or [if] the sentence was in
excess of the maximum authorized by law.” 28 U.S.C.
§ 2255(a). “Relief under § 2255 is available ‘only in extraordinary situations, such as an error of constitutional or jurisdictional magnitude or where a fundamental defect has occurred
which results in a complete miscarriage of justice.’” United
States v. Coleman, 763 F.3d 706, 708 (7th Cir. 2014) (quoting
Blake v. United States, 723 F.3d 870, 878–79 (7th Cir. 2013)).
6 No. 19-3363
When considering the denial of a federal prisoner’s § 2255
motion, we typically review the district court’s legal conclusions de novo. Reyes v. United States, 998 F.3d 753, 757 (7th Cir.
2021). But in the district court, Harris did not properly present
the theory of ineffective assistance that he pursues before us.
His opening motion was barely comprehensible; at most, it
asserted that counsel was ineffective because he should have
challenged his 2006 conviction, but it provided no clear basis
for a challenge.
Harris did raise the Descamps-based argument in his reply
brief, however. He says his citation to Descamps—which requires that a state predicate offense fall within the federal definition—simply “clarified” the claim he raised initially in his
§ 2255 motion. But that did not preserve the issue for appeal.
A movant must present his specific theory of ineffectiveness
in the district court, see Rittenhouse v. Battles, 263 F.3d 689,
694–95 (7th Cir. 2001), with enough detail to allow the government to respond to it, see Wright v. United States, 139 F.3d
551, 553 (7th Cir. 1998). Harris’s opening motion did not alert
the government that he wished his counsel had raised a categorical challenge to his 2006 conviction’s predicate-offense
status. So, unsurprisingly, the government did not respond as
to whether Harris’s prior conviction fit the federal definition
of a “felony drug offense.”
Just so, the government is incorrect to argue that Harris
did not raise this issue in reply. Construing Harris’s pro se
briefing liberally as we must, see McNeil v. United States,
508 U.S. 106, 113 (1993), the citation to Descamps sufficiently
raised the claim that counsel should have made a categorical
challenge. And a categorical challenge requires comparing
not just the elements of a statute but also “the provisions it
No. 19-3363 7
cross-referenc[es].” Brock-Miller v. United States, 887 F.3d 298,
310 (7th Cir. 2018). Here, that includes the drug definition.
Harris urges that any failure by him to preserve this issue
is a forfeiture, not waiver. “Forfeiture results from ‘inadvertence, neglect, or oversight.’” Bourgeois v. Watson, 977 F.3d 620,
631 (7th Cir. 2020) (quoting Henry v. Hulett, 969 F.3d 769, 786
(7th Cir. 2020) (en banc)). Harris contends his failure in the
district court was inadvertent because there he proceeded pro
se. The government counters that the delay was strategic, citing cases that bar litigants from raising an argument for the
first time in a reply brief on appeal to prevent sandbagging.
Harris did not gain any advantage in this delay. The government asserts in its brief that it could have introduced additional evidence “to cast scientific doubt upon the veracity of
the isomer arguments.” But the “isomer argument” is about
the plain language of two statutes and thus purely legal. See
Ruth, 966 F.3d at 648. Further, the government does not argue
that it can show the isomers at issue are “unquestionably nonexistent.” Id. Thus, the government was not prejudiced by its
inability to develop a theoretical factual challenge in the district court and has now fully briefed the legal issue. So, Harris’s conduct here constituted a forfeiture, not a waiver, of this
issue.
The next question is whether to forgive the forfeiture. In
earlier civil appeals, forfeited issues have been considered
where, as here, “failure to present a ground to the district
court has caused no one—not the district judge, not us, not
the appellee—any harm of which the law ought to take note.”
Amcast Indus. Corp. v. Detrex Corp., 2 F.3d 746, 749 (7th Cir.
1993). More recently we clarified that, in the context of a collateral attack on a criminal sentence, a forfeited issue may be
8 No. 19-3363
reviewed for plain error “where a party can demonstrate that:
‘(1) exceptional circumstances exist; (2) substantial rights are
affected; and (3) a miscarriage of justice will occur if plain error review is not applied.’” Bourgeois v. Watson, 977 F.3d 620,
629 (7th Cir. 2020) (quoting Thorncreek Apartments III, LLC v.
Mick, 886 F.3d 626, 636 (7th Cir. 2018)). In Bourgeois, only the
first element was assessed. Id. at 631–32. That decision explained that exceptional circumstances “include when a forfeited ground is ‘founded on concerns broader than those of
the parties,’” such as comity, federalism interests, and the
conservation of judicial resources. Id. at 631 (quoting United
States v. Ford, 683 F.3d 761, 768 (7th Cir. 2012)). And we concluded that those considerations alone could compel us to
look past forfeiture. Id. at 631–32.
Similar considerations induce us to look past Harris’s forfeiture. Despite his failure to raise the issue in his initial § 2255
motion, we are not acting as a court “of first view” in this matter. Arreola-Castillo v. United States, 889 F.3d 378, 383 (7th Cir.
2018). The district court did address this theory of ineffective
assistance on appeal, albeit imperfectly—the court cited to
our past cases denying categorical challenges to some elements of Indiana’s dealing cocaine law without considering
whether a categorical challenge to the definition of an isomer
would succeed. Thus, “to dismiss the case on a procedural
ground at this juncture” risks “effectively discount[ing]” the
district court’s generous efforts to make sense of Harris’s pro
se filings. Id. at 384; see also Anderson v. United States, 981 F.3d
565, 572 (7th Cir. 2020).1
1 We considered whether the district court viewed Harris’s reply brief
as an amendment to his petition, as in Perrone v. United States, 889 F.3d
898, 909 (7th Cir. 2018). There is some support for such a reading. The
No. 19-3363 9
This case also presents a rare circumstance. Two weeks after the district court rejected Harris’s motion, this court ruled
in De La Torre that “the plain language chosen by the Indiana
legislature” for the definition of isomers, incorporated in the
state law definition of cocaine, “dictates that the Indiana
statute is categorically broader than the federal definition of
felony drug offense.” 940 F.3d at 952. We do not blame the
district court for not monitoring our docket, and it was not
that court’s duty to imagine every possible argument for Harris, even when liberally construing his pro se filings. At the
same time, had the district court held off on its decision, it
likely would have become aware of and addressed De La
Torre. Few if any other federal prisoners face the same dilemma as Harris. His motion to vacate his sentence was decided immediately before De La Torre, and he timely appealed
shortly thereafter. Therefore, this decision does not risk opening the floodgates to forfeited issues.
Accordingly, the standard of review here is stringent and
for plain error, as any error in the district court’s conclusion
must be “clear or obvious.” Puckett v. United States, 556 U.S.
129, 135 (2009). As a practical matter, though, our conclusion
here would be the same under de novo review. Harris has not
shown any constitutional error with counsel’s performance,
let alone a “clear or obvious” one.
district court said, for instance, that Harris’s reply brief “clarifies” his
claim of ineffective assistance. Although a district court may not accept
amendments to a § 2255 motion sub silentio, the similarities between this
case and Perrone further support our conclusion that review here is appropriate.
10 No. 19-3363
B
Under Strickland v. Washington, 466 U.S. 668, 687 (1984),
collateral relief is not available unless “counsel’s performance
was deficient” and “the deficient performance prejudiced the
defense.” The parties agree here that if counsel should have
challenged Harris’s predicate offenses, then Harris was prejudiced. See Missouri v. Frye, 566 U.S. 134, 147 (2012) (prejudice
occurs when there is a “reasonable probability” that “the end
result of the criminal process would have been … a sentence
of less prison time”). Without the 2001 and 2006 Indiana
crimes involving cocaine as predicate offenses, Harris’s sentencing guidelines range would have been 121 to 151 months,
substantially shorter than his 240-month prison sentence. So,
we turn to whether counsel’s performance was sufficient despite his failure to raise this challenge.
To show deficient performance, it is not enough to rely on
hindsight about whether a proposed challenge would have
succeeded. See Bridges v. United States, 991 F.3d 793, 802
(7th Cir. 2021). Rather, the reasonableness of counsel’s performance must be assessed “in the context of the law” at the time.
Lilly v. Gilmore, 988 F.2d 783, 786 (7th Cir. 1993).
At the time of Harris’s sentencing, his counsel should have
known about a possible categorical challenge to the predicate
offenses. “In some circumstances, defense counsel may be required to anticipate arguments foreshadowed but not yet
adopted by existing case law.” Bridges, 991 F.3d at 803. By
2017, when Harris was negotiating his guilty plea, the categorical approach was well-established. See id. at 804 (citing
Taylor v. United States, 495 U.S. 575 (1990)). One circuit court
had already applied the categorical approach to the federal
“felony drug offense” definition. See United States v. Ocampo-
No. 19-3363 11
Estrada, 873 F.3d 661, 667 (9th Cir. 2017). Further, this court
has stated repeatedly that comparing statutory definitions is
part of competent representation. See Bridges, 991 F.3d at 805;
Brock-Miller, 887 F.3d at 311 (“Reading statutes and discerning their plain meaning is neither convoluted nor sophisticated; it is what lawyers must do for their clients every day.”).
The government argues that a categorical challenge to Indiana’s definition of an isomer was somehow more complex
than a categorical challenge to any other term in the state
code, and thus too obscure for a competent lawyer to contemplate. That is not convincing, though. Even minimally competent attorneys know how to raise complex legal arguments.
See Bridges, 991 F.3d at 805 (citing cases). And the analysis
called for here was not complex; as the government admits,
counsel only had to compare the plain language of statutes.
Moreover, “[s]entencing advocacy, both during plea negotiations and before a district court, is in most cases the most important task of a federal criminal defender,” requiring close
attention. Id. at 804. Finally, even though no cases had then
adopted the view on isomers that this court has since embraced in Ruth and De La Torre, at least one court had considered the issue before Harris’s sentencing hearing. See United
States v. Jimenez-Ibarra, 695 Fed. App’x 767, 770–72 (5th Cir.
2017).
We do not know whether counsel was aware of a possible
categorical challenge to Indiana’s definition of an isomer. But
remand for a factual hearing is not necessary because counsel’s subjective assessment is not central to the legal analysis
here. Even if counsel’s failure to challenge the predicate offenses had been “inadvertent,” rather than strategic, “relief is
not automatic.” Yarborough v. Gentry, 540 U.S. 1, 8 (2003).
12 No. 19-3363
Rather, “Strickland … calls for an inquiry into the objective
reasonableness of counsel’s performance, not counsel’s subjective state of mind.” Harrington v. Richter, 562 U.S. 86, 110
(2011). And Strickland makes clear that even under this objective standard, “[j]udicial scrutiny of counsel’s performance
must be highly deferential.” 466 U.S. at 689.
We must assess counsel’s performance by considering the
options available to the defense when Harris pleaded guilty
and was sentenced. The record shows that regardless of
whether counsel was aware of it, he had two choices. Counsel
could advise Harris to accept the government’s plea offer to
drop one potential predicate offense, thereby significantly reducing Harris’s sentencing exposure to a guarantee of 20
years (given a FED. R. CRIM. P. 11(c)(1)(C) binding agreement).
Or, counsel could advise Harris to challenge his predicate offenses. If the challenge was successful, Harris would not have
a mandatory minimum sentence. But if the challenge was unsuccessful, Harris would face a mandatory life sentence. And
if counsel raised the challenge, the government might have
withdrawn its plea offer.
Significantly, the challenge would have required counsel
to “ask[] the court to break new legal ground.” Bridges,
991 F.3d at 808. At the time of sentencing, no case law held
that any state defined isomers more broadly than the federal
government. At that point, the only circuit court to compare
state to federal definitions of “isomers” rejected the argument
that the state’s definition was too broad. See Jimenez-Ibarra,
695 Fed. App’x at 770–72. The next circuit-level case, and the
first to accept the isomer argument, was not decided until almost one year after Harris’s sentencing. See Lorenzo v. Sessions,
902 F.3d 930, 935–56 (9th Cir. 2018), superseded on denial of
No. 19-3363 13
rehearing on other grounds as Lorenzo v. Whitaker, 752 Fed.
App’x 482 (9th Cir. 2019).
Harris presses that counsel should have at least consulted
with him about the option of a novel challenge to the predicate offenses. He correctly points out that, “[i]n the plea bargaining context,” counsel must “make an estimate of a likely
sentence” and “communicate the results of that analysis before allowing his client to plead guilty.” Gaylord v. United
States, 829 F.3d 500, 506 (7th Cir. 2016). In Gaylord, this court
determined that defense counsel may have been ineffective
because he failed to consult with the defendant about a potential challenge to a sentence enhancement, thus failing to provide him “with the information necessary for a knowing and
voluntary guilty plea.” Id. at 507. But in Gaylord, the potential
challenge was based on established law. Counsel advised the
defendant to plead guilty in 2011, without mentioning a viable challenge to his sentence enhancement that had been established more than a year prior, in United States v. Hatfield,
591 F.3d 945, 948 (7th Cir. 2010). It would stretch Gaylord too
far to read it as requiring counsel to raise with their client
every potential sentencing challenge. Counsel are not required “to obtain the defendant’s consent to ‘every tactical decision,’” particularly those within an attorney’s expertise.
Florida v. Nixon, 543 U.S. 175, 187 (2004) (quoting Taylor v. Illinois, 484 U.S. 400, 417–18 (1988)). And the “isomer” challenge
at issue here was too unprecedented to warrant discussion
with the client.
In sum, the defense essentially had a bird in the hand—the
plea offer with a set 20-year sentence—with a possibility of
two in the bush—the novel challenge to the predicate offenses
with the risk of a mandatory life sentence. Faced with these
14 No. 19-3363
options, it was objectively reasonable for Harris’s counsel to
pursue the plea deal. See Harris v. United States, 366 F.3d 593,
596 (7th Cir. 2004) (ruling counsel not deficient for declining
to press an unsettled legal question when doing so would
have detracted from defendant’s efforts to obtain a lesser sentence).

Outcome: The district court did not plainly err in denying Harris’s
§ 2255 petition, so that court’s decision is AFFIRMED.

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