In the

United States Court of Appeals

For the Seventh Circuit ____________________ 

No. 22-1678 

FREDERICK J. COLEMAN, 

Petitioner-Appellant, 

v.

UNITED STATES OF AMERICA, 

Respondent-Appellee. 

____________________ 

Appeal from the United States District Court for the

Central District of Illinois. 

No. 4:17-cv-4270 — Sara Darrow, Chief Judge. 

____________________ 

ARGUED FEBRUARY 15, 2023 — DECIDED AUGUST 15, 2023 

____________________ 

Before EASTERBROOK, WOOD, and LEE, Circuit Judges. 

LEE, Circuit Judge. In 2014, Frederick Coleman was sentenced to life imprisonment for conspiring to distribute crack 

cocaine. The district judge based the sentence on 21 U.S.C. 

§ 841(b)(1)(A), which, at the time, mandated a life sentence for 

a defendant who previously had committed two or more felony drug offenses. After we denied his direct appeal, Coleman filed a pro se motion under 28 U.S.C. § 2255 to vacate his 

sentence, arguing that his defense counsel had provided 
2 No. 22-1678 

ineffective assistance by not informing him of the potential 

life sentence. Later, he filed a motion to amend his pleading, 

expanding on his allegations, but, by that time, the limitations 

period had run. After ruling against Coleman on his original 

claim, the district court denied the motion to amend, finding 

that the amendment did not “relate back” to his initial pleading. Because the district court abused its discretion in reaching that conclusion, we reverse and remand for further proceedings as to Coleman’s amended ineffective assistance of 

counsel claim.

I. BACKGROUND

In 2013, Coleman was convicted of conspiring to distribute 

crack cocaine. See 21 U.S.C. §§ 841(a)(1), (b)(1)(A), 846. Pursuant to the Controlled Substances Act in effect at that time, 

Coleman was sentenced to the statutorily mandated term of 

life imprisonment based on having at least two prior convictions for a “felony drug offense.” Id. § 841(b)(1)(A) (2012).1 We 

affirmed his sentence on direct appeal. United States v. Brown, 

822 F.3d 966, 976 (7th Cir. 2016). 

Coleman then filed a timely pro se motion to vacate his sentence pursuant to 28 U.S.C. § 2255. Coleman’s § 2255 motion 

asserted, among other things, that his appointed counsel, Anthony Vaupel, was ineffective for having failed to inform him 

of the government’s pretrial 21 U.S.C. § 851 Notice of Enhancement. This notice informed Coleman that, should he be 

1 The First Step Act of 2018, enacted after Coleman’s sentencing, reduced the mandatory minimum sentences from life to 25 years’ imprisonment for a defendant having two or more prior convictions for a “serious 

drug felony” or “serious violent felony.” Pub. L. 115-391, § 401(a)(2)(A)(ii), 

132 Stat. 5194, 5220 (2018).
No. 22-1678 3

found guilty at trial, the government would seek to enhance 

his sentence to life imprisonment based on his prior Illinois 

cocaine-related convictions, which, it believed, qualified as 

“felony drug offenses” under 21 U.S.C. § 841(b)(1)(A). According to Coleman, had Vaupel shown him this notice, he 

never would have agreed to go to trial.

To inquire into these allegations, the district court first entered an order that Coleman had waived the attorney-client 

privilege as to his communications with Vaupel regarding 

“the government filing a section 851 notice and [Coleman]’s 

potential life sentence.” It also ordered Vaupel to submit an 

affidavit addressing Coleman’s claim.

In his affidavit, Vaupel stated that he had informed Coleman on more than one occasion that he faced, and would receive, a mandatory life sentence if found guilty. Vaupel also 

attested that he had told Coleman that the mandatory life sentence was due to his prior convictions, and that despite the 

government’s willingness to enter a proffer agreement with 

Coleman, it was unwilling to waive the § 851 enhancement.

Before the district court ruled on Coleman’s § 2255 motion, Coleman moved, again pro se, to amend it pursuant to 

Federal Rule of Civil Procedure 15(c). His amendment contained more detailed allegations and argued specifically that 

Vaupel was ineffective by failing to object to the § 851 notice 

on the grounds that, under the categorical approach espoused 

in Taylor v. United States, 495 U.S. 575 (1990), Coleman’s prior 

Illinois cocaine convictions did not qualify as “felony drug offenses” under § 841(b)(1)(A) given that Illinois defined “cocaine” more broadly than federal law.
4 No. 22-1678 

The district court denied Coleman’s initial § 2255 motion, 

as well as his motion to amend. Without reaching the merits 

of the amended claim, the court determined that Coleman’s 

motion to amend did not relate back to his initial pleading because “the claims rest[ed] on distinct types of attorney misfeasance and [we]re supported by different facts.” Coleman v. 

United States, No. 4:17-cv-04270-SLD-JEH, 2022 WL 673702, at 

*8 (C.D. Ill. Mar. 7, 2022). And because Coleman’s motion to 

amend was filed more than a year after his conviction became 

final, the district court found it untimely. Id. at *9; see 28 U.S.C. 

§ 2255(f)(1) (providing a one-year statute of limitations for 

collateral review). Then, finding that reasonable jurists may 

disagree on this point, the district court granted Coleman a 

certificate of appealability on his claim.2 Id. Coleman appealed, and we recruited counsel.3

II. DISCUSSION

Section 2255 provides a federal prisoner with the means to 

collaterally attack the propriety of his sentence. Relief under 

this statute is an “extraordinary remedy,” and therefore only 

available in limited circumstances. Almonacid v. United States, 

476 F.3d 518, 521 (7th Cir. 2007). One such circumstance is 

where defense counsel’s representation is so ineffective that it 

2 Coleman’s § 2255 motion alleged Vaupel was constitutionally ineffective in three other ways. The district court denied relief, as well as a 

certificate of appealability, on each of those grounds. See Coleman, 

2022 WL 673702, at *5–*7, *9. Our review is therefore limited to Coleman’s 

claim relating to Vaupel’s treatment of the government’s § 851 notice.

3 We thank Coleman’s counsel, Marc Krickbaum, as well as his colleague Katherine Stallings Bailey of Winston & Strawn LLP, for their advocacy on Coleman’s behalf.
No. 22-1678 5

violates the defendant’s Sixth Amendment rights. U.S. Const. 

amend. VI; Strickland v. Washington, 466 U.S. 668, 686 (1984). 

Coleman argues that his appointed counsel was constitutionally ineffective by failing to object to the § 851 notice. As he 

sees it, his attorney should have argued that Coleman’s prior 

convictions did not qualify as “felony drug offenses” that 

could be used to enhance his sentence to life imprisonment 

under § 841. See generally United States v. Ruth, 966 F.3d 642 

(7th Cir. 2020).4

Before we can reach the merits of Coleman’s ineffective assistance of counsel claim, however, we must resolve two preliminary questions. First, we must determine whether appellate review of a district court’s disposition of a pleading 

amendment under the “relation-back” provision of Federal 

Rule of Civil Procedure 15(c) is de novo or for an abuse of discretion. We must then apply that standard to determine the 

propriety of the district court’s conclusion that Coleman’s 

amendment did not relate back to the filing of his original motion.

A. Standard of Review

When a party seeks to amend its pleading, district courts 

“should freely give leave when justice so requires.” Fed. R. 

Civ. P. 15(a)(2). “The Supreme Court has interpreted this rule 

to require a district court to allow amendment unless there is 

a good reason—futility, undue delay, undue prejudice, or bad 

4 Coleman’s amended motion was filed prior to our holding in Ruth

that an Illinois conviction for possession with intent to distribute cocaine 

was not a “felony drug offense” under the federal sentencing laws because 

Illinois’s definition of “cocaine” was broader than the federal definition. 

966 F.3d at 650.
6 No. 22-1678 

faith—for denying leave to amend.” Life Plans, Inc. v. Sec. Life 

of Denver Ins. Co., 800 F.3d 343, 357–58 (7th Cir. 2015) (citing 

Foman v. Davis, 371 U.S. 178, 182 (1962)). This “liberal standard,” id. at 357, is limited, however, by any applicable statute 

of limitations. See Mayle v. Felix, 545 U.S. 644, 655 (2005). 

Where a party seeks to amend a pleading after the statute 

of limitations has run, he must turn to the relation-back provision of Rule 15(c), which allows such amendment if it “asserts a claim or defense that arose out of the conduct, transaction, or occurrence set out—or attempted to be set out—in the 

original pleading.” Fed. R. Civ. P. 15(c)(1)(B).

It is well-settled that review of a district court’s disposition 

of a motion to amend under Rule 15(a) is for an abuse of discretion.5 See, e.g., Foman, 371 U.S. at 182 (“Of course, the grant 

or denial of an opportunity to amend [under Rule 15(a)] is 

within the discretion of the District Court[.]”); Runnion ex rel. 

Runnion v. Girl Scouts of Greater Chi. & Nw. Ind., 786 F.3d 510, 

524 (7th Cir. 2015) (applying deferential review but noting 

that, where a district court’s denial is futility-based, our review “includes de novo review of the legal basis for the futility”). But we have been less clear on the appropriate standard 

of review when a district court decides whether a proposed 

amendment “relates back” to a pleading under Rule 15(c). Indeed, over six years ago, we made a mental note to “clarify 

the correct standard in a future case when the matter is 

properly before the court.” Mulvania v. Sheriff of Rock Island 

Cnty., No. 16-1711, 2017 WL 2726577, at *2 (7th Cir. May 16, 

5 The same is true for amendments made under Rule 15(b), which 

governs amendments during and after trial. See Aldridge v. Forest River, 

Inc., 635 F.3d 870, 875 (7th Cir. 2011).
No. 22-1678 7

2017) (denying petition for rehearing en banc). Compare Arreola v. Godinez, 546 F.3d 788, 796 (7th Cir. 2008) (applying abuse 

of discretion review), O’Brien v. Ind. Dep’t of Corr. ex rel. 

Turner, 495 F.3d 505, 507 (7th Cir. 2007) (same), and Bibbs v. 

Sheriff of Cook Cnty., 618 F. App’x 847, 851 (7th Cir. 2015) 

(same), with Delgado-Brunet v. Clark, 93 F.3d 339, 342 (7th Cir. 

1996) (applying de novo review).6 With this issue squarely before us, we make clear that a district court’s disposition of a 

motion to amend a pleading that turns on the “relation-back” 

provision of Rule 15(c) is reviewed for an abuse of discretion.

As an initial matter, the fact that this issue comes to us via 

a § 2255 proceeding is of no consequence. Habeas corpus 

cases under § 2255 are civil cases generally governed by the 

Federal Rules of Civil Procedure. Conley v. United States, 

5 F.4th 781, 794 (7th Cir. 2021) (citing Banister v. Davis, 

140 S. Ct. 1698, 1705 (2020)); see Beason v. Marske, 926 F.3d 932, 

938 (7th Cir. 2019) (discussing application of Rule 15’s 

6 We also observe a split of authority in our sister circuits on this question. Compare United States v. Ciampi, 419 F.3d 20, 23 (1st Cir. 2005) (applying abuse of discretion review in § 2255 context), United States v. Pittman, 

209 F.3d 314, 316 (4th Cir. 2000) (same), Mandacina v. United States, 

328 F.3d 995, 1000 (8th Cir. 2003) (same), Davenport v. United States, 

217 F.3d 1341, 1343 n.4 (11th Cir. 2000) (same), with Slayton v. Am. Exp. Co., 

460 F.3d 215, 227–28 (2d Cir. 2006) (applying de novo review), United States 

v. Santarelli, 929 F.3d 95, 100 (3d Cir. 2019) (same in § 2255 context), Durand 

v. Hanover Ins. Grp., Inc., 806 F.3d 367, 374 (6th Cir. 2015) (applying de novo 

review), United States v. Marulanda, 226 F. App’x 709, 710 (9th Cir. 2007)

(same in § 2255 context), United States v. Roe, 913 F.3d 1285, 1298 (10th Cir. 

2019) (same), and Anza Tech., Inc. v. Mushkin, Inc., 934 F.3d 1359, 1367 (Fed. 

Cir. 2019) (applying de novo review). The Fifth Circuit declined to resolve 

this issue in the § 2255 context in United States v. Alaniz, 5 F.4th 632 (5th 

Cir. 2021), but noted that “[its] cases tend to apply the abuse of discretion 

standard.” Id. at 635 n.2.
8 No. 22-1678 

relation-back provision to a § 2255 motion); Fed. R. Civ. P. 

81(a)(4). See generally Mayle, 545 U.S. at 655 (applying Rule 

15(c) to § 2244 habeas corpus proceedings). Accordingly, our 

holding today applies generally to the relation-back provision 

of Rule 15(c); it is not limited to habeas proceedings.

Determining whether a proposed amendment asserts a 

claim arising from the same conduct, transaction, or occurrence involves more than a facial comparison of the original 

and amended pleadings. In making this assessment, district 

courts also must consider whether, under the particular circumstances of the litigation, the opposing party has been put 

on notice as to the claim raised in the proposed amendment. 

See Supreme Auto Transp., LLC v. Arcelor Mittal USA, Inc., 

902 F.3d 735, 741 (7th Cir. 2018) (“The central inquiry under 

Rule 15(c) is whether the original complaint ‘gave the defendant enough notice of the nature and scope of the plaintiff’s 

claim that he shouldn’t have been surprised by the amplification of the allegations of the original complaint in the 

amended one.’”) (quoting Santamarina v. Sears, Roebuck & Co., 

466 F.3d 570, 573 (7th Cir. 2006)); see also Krupski v. Costa Crociere S. p. A., 560 U.S. 538, 550 (2010) (explaining that the purpose of relation back is “to balance the interests of the defendant protected by the statute of limitations with the preference 

expressed in the Federal Rules of Civil Procedure in general, 

and Rule 15 in particular, for resolving disputes on their merits”).

In some cases, it may be clear from the face of the proposed 

amendment that the original pleading put the defendant on 

notice of a later-added claim. See, e.g., Tiller v. Atl. Coast Line 

R.R. Co., 323 U.S. 574, 581 (1945) (finding that a new legal theory related back where defendant was on notice “from the 
No. 22-1678 9

beginning that [plaintiff] was trying to enforce a claim against 

it” based on the same facts alleged in the complaint). In others, it may be clear from the face of the proposed amendment 

that the opposing party was not on notice of such a claim. See, 

e.g., Mayle, 545 U.S. at 648–49 (no relation back where petitioner initially claimed that admission of videotaped testimony from a prosecution witness violated the Sixth Amendment’s Confrontation Clause, but his amended claim asserted 

that the admission of his own pretrial testimony violated the 

Fifth Amendment right against self-incrimination).

But there will be those cases in the middle, where the district court’s familiarity with and proximity to the parties and 

proceedings will help it decide whether a defendant would 

(or reasonably should) be “surprised by the amplification” of 

the plaintiff’s originally asserted claims. Supreme Auto, 

902 F.3d at 741. Such decisions involving questions that “immerse courts in case-specific factual issues” we typically review under the abuse-of-discretion standard. U.S. Bank Nat’l 

Ass’n ex rel. CWCapital Asset Mgmt. LLC v. Vill. at Lakeridge, 

LLC, 138 S. Ct. 960, 967 (2018).

We find our analysis in Supreme Auto instructive. There, 

the district court determined that the plaintiffs’ amended 

claims did not relate back to the initial complaint because the 

transactions at issue “were wholly distinct” from those of the 

amended complaint. 902 F.3d at 741. We agreed. But we based 

our conclusion on more than a facial comparison of the two 

pleadings; we also looked to the parties’ representations of 

the scope of the dispute throughout the course of litigation. 

Id. at 741–42. Viewing the dispute through this lens, we concluded that at no time prior to the plaintiffs’ proposed amendment could the defendant have reasonably expected to defend 
10 No. 22-1678 

against the “wholly distinct” newly alleged conduct. See id.

(“What’s more, Supreme Auto gave no indication during the 

first seven years of litigation that its suit included any more 

products other than [those alleged in the initial complaint].”). 

Although we did not clarify in Supreme Auto the standard under which we reviewed the district court’s decision, when reviewing mixed questions of fact and law, the standard turns 

on “which ‘judicial actor is better positioned’ to make the decision.” U.S. Bank, 138 S. Ct. at 967 (quoting Miller v. Fenton, 

474 U.S. 104, 114 (1985)). Because the district court in Supreme 

Auto had been steeped in the circumstances of that case for ten 

years before it reached us, we had no doubt the district court 

was better positioned to determine whether the defendant 

was or should have been on notice of the plaintiffs’ amended 

claims.

In sum, because the application of Rule 15(c)’s “relationback” provision requires a district court to consider whether 

a nonmoving party would have been on notice of the moving 

party’s amended claims based on all the relevant circumstances of a particular case, our review of a district court’s application of that rule is for an abuse of discretion.7

7 We are not persuaded by Coleman’s reliance on Krupski to argue that 

the “mandatory nature” of the Rule 15(c) inquiry signals de novo review. 

560 U.S. at 553. Krupski merely holds that, once a district court finds that 

all the requirements of Rule 15(c) are satisfied, the district court has no 

discretion to deny the amendment. See id. It does not hold, as Coleman 

suggests, that the district court lacks discretion to determine whether 

those requirements are satisfied in the first place.
No. 22-1678 11

B. Relation Back

Even under the deferential standard we have settled on today, it is not difficult for us to conclude that, in this case, the 

district court abused its discretion in denying Coleman’s motion to amend.

As already noted, “amendments relate back to the date of 

the original pleading when the claim asserted in the amended 

plea ‘arose out of the conduct, transaction, or occurrence set 

forth or attempted to be set forth in the original pleading.’” 

Mayle, 545 U.S. at 656 (quoting Fed. R. Civ. P. 15(c)(2)). Even 

where an amendment “invoke[s] a legal theory not suggested 

by the original complaint and relie[s] on facts not originally 

asserted,” relation back is in order “[s]o long as the original 

and amended petitions state claims that are tied to a common 

core of operative facts.” Id. at 659, 664. Indeed, “[e]ven ‘significant’ changes to a complaint ... can relate back so long as the 

defendant had fair notice of the substance of the new allegations from the outset.” Supreme Auto, 902 F.3d at 741.

Construing Coleman’s original pro se § 2255 petition liberally, as we must, see Erickson v. Pardus, 551 U.S. 89, 94 (2007), 

we conclude that the government was reasonably on notice of 

the claims contained within Coleman’s amended petition. 

Those claims are substantively similar in time and type to 

those asserted in his original motion: his attorney’s failure to 

provide legal advice as to the contents and impact of the § 851 

notice.

Coleman’s original § 2255 motion advanced an ineffective 

assistance of counsel claim based on his attorney’s failure to 

“inform” him of the government’s § 851 notice that the government would use Coleman’s prior convictions to enhance 
12 No. 22-1678 

his sentence to life imprisonment if he lost at trial. His 

amended petition sought to expand on this claim to allege 

that his attorney failed to adequately “research, investigate, 

or inform” Coleman whether those prior convictions could be 

used to support a sentencing enhancement under § 851 at all. 

Comparing these two claims, the district court acknowledged 

that, “broadly speaking,” both the original and amended 

claims challenged his attorney’s conduct as to the § 851 notice. 

Coleman, 2022 WL 673702, at *8. Nevertheless, the district 

court concluded that the two claims were “supported by different facts,” and therefore the amendment did not relate 

back. Id. In the district court’s view, “[w]hile the original petition contained a claim centered on an alleged failure to inform Coleman of the § 851 notice prior to Coleman’s decision 

to go to trial, the new claims center on substantive failures of 

counsel throughout case preparation, client counseling, plea 

negotiations, and at sentencing.” Id.

This is too crabbed a view of Coleman’s claims, particularly given his pro se status at the time. The fact that an 

amended claim may involve some different facts than those 

originally alleged does not necessarily mean that that claim is 

not tied to the original claim via a “common core of operative

facts.” Mayle, 545 U.S. at 664 (emphasis added). Coleman’s 

success on either of his theories would require the district 

court to inquire into his attorney’s treatment of the § 851 notice and the adequacy of advice he provided to Coleman as to 

the impact the notice may have had on the case. This commonality is enough to unite the claims.

We also fail to see how the government could have reasonably been surprised by Coleman’s amended claim. The government no doubt encounters countless pro se filings such as 
No. 22-1678 13

this and knows that they must be construed liberally. Coleman’s allegations that his attorney had inadequately counseled him regarding the § 851 notice and the convictions listed 

therein were enough to put the government on notice that 

Coleman might challenge the use of those convictions for the 

enhancement. Furthermore, the district court alerted the parties that, by filing his original motion, Coleman had waived 

the attorney-client privilege as to “any and all communications 

between [Coleman] and Mr. Vaupel relating to ... the government filing a section 851 notice and [Coleman]’s potential life 

sentence.” Text Order of 1/5/18 (emphasis added). This order 

was sufficiently broad to uncover the facts underlying Coleman’s amended claims. Accordingly, on balance, any prejudice the government may suffer by allowing the amended 

complaint to relate back to the original filing is outweighed 

by “the preference expressed in the Federal Rules of Civil Procedure in general, and Rule 15 in particular, for resolving disputes on their merits.” Krupski, 560 U.S. at 550. 

We therefore find that the district court abused its discretion in determining that Coleman’s amended § 2255 pleading 

did not relate back to his original motion. Finding that Coleman’s amendment was timely under the provisions of Rule 

15(c), we turn to the merits of his ineffective assistance of 

counsel claim.

C. Ineffective Assistance of Counsel

Under Strickland, Coleman is not entitled to collateral relief on his claim unless he can establish that (1) his attorney’s 

“performance was deficient” and (2) “the deficient performance prejudiced the defense.” 466 U.S. at 687. 
14 No. 22-1678 

1. Performance

We begin by considering whether defense counsel’s failure to challenge the use of Coleman’s prior Illinois cocaine 

convictions in the § 851 notice to enhance Coleman’s sentence 

was constitutionally deficient. As we have noted elsewhere, 

“[s]uch an argument, novel then, would succeed today.” Harris v. United States, 13 F.4th 623, 625 (7th Cir. 2021); see Ruth,

966 F.3d at 650 (applying the categorical approach established 

in Taylor and holding that Illinois cocaine convictions are not 

“felony drug offenses” that can be used to enhance a sentence 

under § 841(b)(1)(C)). But, to succeed on this first prong, Coleman must show that his counsel’s performance “fell below an 

objective standard of reasonableness.” Strickland, 466 U.S. at 

688. 

We have long recognized the general principle that “[t]he 

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); Strickland, 466 U.S. at 689. “Rather, the reasonableness of counsel’s performance must be assessed ‘in the 

context of the law’ at the time.” Harris, 13 F.4th at 629 (quoting 

Lilly, 988 F.2d at 786). Nevertheless, “there are some circumstances where [defense counsel] may be obliged to make, or 

at least to evaluate, an argument that is sufficiently foreshadowed in existing case law.” Bridges v. United States, 991 F.3d 

793, 804 (7th Cir. 2021) (citations omitted).

In Harris, we determined that defense counsel should have 

known about a possible categorical challenge to the use of Illinois cocaine convictions as predicate offenses—the same 

that succeeded in Ruth—at least as early as 2017. 13 F.4th at 

629 (“By 2017, ... the categorical approach was well-established.”) (citing Bridges, 991 F.3d at 803). And the groundwork 
No. 22-1678 15

for such an argument was, at the very least, foreshadowed by 

numerous decisions issued before 2014 (the year Coleman 

was sentenced) that applied the categorical approach to predicate offenses in other contexts. See, e.g., Descamps v. United 

States, 570 U.S. 254, 264–65 (2013) (concluding that a California burglary conviction could not serve as a predicate offense 

under the Armed Career Criminal Act (“ACCA”) because the 

state statute was broader than generic burglary); United States 

v. Tucker, 703 F.3d 205, 209 (3d Cir. 2012) (applying categorical 

approach of Taylor to determine if prior convictions qualify as 

“serious drug offenses” under ACCA); United States v. Bynum, 

669 F.3d 880, 885 (8th Cir. 2012) (same); Ruiz-Vidal v. Gonzales, 

473 F.3d 1072, 1078 (9th Cir. 2007), abrogated on other grounds 

by Kwong v. Holder, 671 F.3d 872 (9th Cir. 2011) (holding that 

California’s definition of “controlled substance” was broader 

than the federal definition because California “punishe[d] the 

possession of optical and geometrical isomers” of methamphetamine while federal law “punishe[d] the possession of 

optical isomers alone”); Samas v. United States, No. 3:10-CV422 (JCH), 2011 WL 221866, at *4 (D. Conn. Jan. 20, 2011) (concluding that § 2255 petitioner’s state conviction was not a “felony drug offense” because two analogs of fentanyl criminalized in the Connecticut narcotics statute were not “narcotic 

drug[s]” as defined by federal law). These cases demonstrate 

that, although the categorical approach had not yet been applied to prior convictions like Coleman’s by 2014, the framework for making such a challenge had been established.

What is more, in White v. United States, 8 F.4th 547, 557 (7th 

Cir. 2021), we determined (albeit under different 
16 No. 22-1678 

circumstances)8 that “a challenge to cocaine delivery predicate offenses was neither novel ... nor foreclosed” in as early 

as 2013. And we recognized that the “basis and authority” for 

Ruth had been established as early as 1990, when “the Supreme Court first laid out the categorical approach in [Taylor] 

and when the relevant portions of the Illinois and federal drug 

statutes had taken their current form.” White, 8 F.4th at 556. 

Given that there was no adverse precedent foreclosing the viability of such a challenge in 2013, we held that the petitioner 

had procedurally defaulted his argument by failing to timely 

raise it in his direct appeal. See id. Similarly, here, we are unpersuaded by the government’s argument that application of 

the categorical approach to cocaine isomers was too novel in 

2014 to have been recognized by competent defense counsel. 

As we have “repeatedly” made clear, “comparing statutory 

definitions is part of competent representation,” and application of the categorical approach to drug isomers is “not complex.” Harris, 13 F.4th at 630.9 

Accordingly, we hold that it would have been objectively 

unreasonable for Coleman’s defense counsel to have not even 

considered a categorical challenge to the government’s reliance 

on prior Illinois cocaine convictions to enhance Coleman’s 

sentence. This is particularly true given that an enhanced sentence here would have resulted in a mandatory life sentence. 

8 White concerned a collateral challenge to the constitutionality of the 

petitioner’s sentence. See id. at 551. It did not address whether defense 

counsel was constitutionally ineffective for failing to raise such a challenge.

9 Indeed, in Harris, “the government admit[ted that] counsel only had 

to compare the plain language of the statutes” to determine if the predicate Indiana cocaine offenses were “felony drug offenses.” 13 F.4th at 630.
No. 22-1678 17

Of course, if counsel did consider the argument but had credible strategic reasons for not raising it, that would be a different question. See id. at 631. But because the claim alleged in 

Coleman’s amended § 2255 motion, if proven, would entitle 

him to relief, we find that an evidentiary hearing on this issue 

is necessary. See Kafo v. United States, 467 F.3d 1063, 1067 (7th 

Cir. 2006). On remand, the district court should determine 

whether Vaupel considered the possibility of a categorical 

challenge to Coleman’s predicate offenses. And, if he did consider it, what reasons he had for not raising it.

2. Prejudice

To succeed on his claim, Coleman also must establish that 

he was prejudiced by defense counsel’s purportedly deficient 

performance. “[P]rejudice occurs when there is a ‘reasonable 

probability’ that ‘the end result of the criminal process would 

have been ... a sentence of less prison time.’” Harris, 13 F.4th 

at 629 (quoting Missouri v. Frye, 566 U.S. 134, 147 (2012)). Coleman has met his burden.

We have held that, in cases where a court relies on an incorrectly calculated Guidelines range to sentence a defendant, 

a reasonable probability of prejudice is presumed absent unusual circumstances. Bridges, 991 F.3d at 808–09 (citing Molina-Martinez v. United States, 578 U.S. 189, 200–01 (2016)); see 

United States v. Wylie, 991 F.3d 861, 864 (7th Cir. 2021) (same); 

see also United States v. Coby, 65 F.4th 707, 713–14 (4th Cir. 

2023) (same). This principle comes from Molina-Martinez, 

where the Supreme Court observed that “a defendant who 

has shown that the district court mistakenly deemed applicable an incorrect, higher Guidelines range has demonstrated a 

reasonable probability of a different outcome.” 578 U.S. at 

200. But the Court was cautious, observing that “[t]here may 
18 No. 22-1678 

be instances when, despite [the error], a reasonable probability of prejudice does not exist,” such as when the record 

shows that the district court would have given the same sentence in any event. 578 U.S. at 200. Only in these “unusual circumstances,” the Court held, was the defendant “required to 

show more” to meet his burden. Id. at 201. We see no reason 

why a court’s purportedly erroneous application of a statutorily mandated minimum sentence, where it is stripped of all 

sentencing discretion, should be treated differently.

The allegations of prejudice in Coleman’s § 2255 petition, 

which went unchallenged both in the district court and on appeal, are sufficient to support application of the presumption 

here.10 As Coleman observes, absent the district court’s application of the § 851 enhancement, he would not have been subject to a mandatory life sentence and the district court would 

have had discretion to sentence him after full and fair consideration of the sentencing factors of 18 U.S.C. § 3553(a). To be 

sure, as Coleman acknowledges, at the sentencing hearing, 

the district court noted that, even if it had the discretion to 

impose a lower sentence, it would have “seriously consider[ed]” imposing life imprisonment. But therein lies the 

rub—the district court had no discretion whatsoever. Even if 

it would have considered a life sentence (in the counterfactual 

scenario), the record falls short of indicating that this is what 

the court actually would have done. Given the significant 

stakes of such a sentence, combined with the district court’s 

lack of sentencing discretion, we are comfortable concluding

10 Indeed, the entirety of the government’s position, here and below, 

was that the argument was too novel in 2014 to succeed—an argument we 

have already rejected. A bald speculation that an argument would have 

been unsuccessful does not preclude a finding of prejudice.
No. 22-1678 19

that Coleman sufficiently alleged that he was prejudiced by 

his counsel’s purportedly deficient performance.

III. CONCLUSION

For these reasons, we REVERSE the district court’s determination that Coleman’s amended § 2255 motion did not relate back to the original motion and REMAND the case to the 

district court to hold an evidentiary hearing consistent with 

this opinion.
20 No. 22-1678 

EASTERBROOK, Circuit Judge, dissenting. I agree with my 

colleagues about the standard of appellate review and with 

their conclusion that the district court should have entertained the petition as amended. But I do not think that a remand is necessary.

Coleman was sentenced in 2014, long before United States 

v. Ruth, 966 F.3d 642 (7th Cir. 2020), held that the way Illinois 

law defines “cocaine” means that cocaine convictions in Illinois do not count toward federal recidivist sentencing. (Illinois defines as cocaine the products of coca leaves, including 

optical, positional, and geometric isomers; federal law mentions only optical and geometric isomers.) Not until 2018 did 

any court of appeals reach the conclusion that Ruth adopted 

in 2020. See Lorenzo v. Sessions, 902 F.3d 930, 935–36 (9th Cir. 

2018). As of 2014 neither any court of appeals nor any federal 

district court had held that a state-law reference to positional 

isomers disqualifies a cocaine conviction for federal purposes. 

The tools that led to Ruth existed—the “categorical approach” 

of Taylor v. United States, 495 U.S. 575 (1990), and its successors, plus the texts of the state and federal statutes—but tools 

exist to make thousands of legal inquiries and arguments.

Most inquiries come up dry, and most novel arguments flop. 

That’s why lawyers usually limit their research to lines that 

have support in judicial decisions. In 2014 an argument about 

positional isomers had none.

Ruth’s novelty is a reason why we held it non-retroactive. 

See White v. United States, 8 F.4th 547, 556–57 (7th Cir. 2021). 

And in Harris v. United States, 13 F.4th 623 (7th Cir. 2021), we 

rejected an effort to make Ruth retroactive indirectly, by treating as ineffective assistance a lawyer’s failure to make a Ruthlike argument before Ruth was issued. Harris observes that 
No. 22-1678 21 

counsel are not expected to be prescient and that legal work 

should not be condemned with the benefit of hindsight.

Yet that is exactly what my colleagues do today. They observe (as Ruth, White, and Harris all state) that the tools to 

make a Ruth-like argument existed in 2014 and hold that 

counsel therefore should have at least done the research to 

find the ingredients of such an argument and contemplated 

the possibility of advancing it. This is hard to reconcile with

Harris and harder to reconcile with the principles established 

in Strickland v. Washington, 466 U.S. 668 (1984), the genesis of 

modern ineffective-assistance law.

“The proper measure of attorney performance remains 

simply reasonableness under prevailing professional norms.” 

Strickland, 466 U.S. at 688. Did “professional norms” in 2014 

require lawyers to investigate a potential legal argument with 

zero support in decided cases? I don’t think so. Attorneys representing criminal defendants have dozens of potentially important tasks, and like physicians they must engage in triage. 

The important issues, those with the largest potential returns, 

must be seen to—and then counsel must move to the defense 

of other clients. In determining what is most likely to be productive, a reasonable attorney uses as cues what has been productive. The number of potential lines of investigation and argument that have never succeeded in any court is large, as is 

the cost of investigating all of them, but the anticipated return 

is small. Sometimes a novel argument will prevail—that’s 

what happened in Ruth—but only with the aid of hindsight 

can a court say that it was so likely to prevail that any reasonable lawyer would have pursued it.

Judicial scrutiny of counsel’s performance must 

be highly deferential. It is all too tempting for a 
22 No. 22-1678 

defendant to second-guess counsel’s assistance 

after conviction or adverse sentence, and it is all 

too easy for a court, examining counsel’s defense after it has proved unsuccessful, to conclude that a particular act or omission of counsel 

was unreasonable. A fair assessment of attorney 

performance requires that every effort be made 

to eliminate the distorting effects of hindsight, 

to reconstruct the circumstances of counsel’s 

challenged conduct, and to evaluate the conduct 

from counsel’s perspective at the time. 

Strickland, 466 U.S. at 689 (internal citation omitted). Only 

through hindsight could a court say that, in 2014, every reasonable lawyer would have investigated the possibility that a 

state law’s unusual reference to positional isomers of cocaine 

would eliminate the use of a cocaine conviction in a federal 

recidivist prosecution.

One may be tempted to reply that Taylor itself is support 

for the sort of argument that prevailed in Ruth. In a general 

sense, that’s true. But only in a general sense. If we define support at a high level of generality, then every lawyer must investigate every argument, for every argument has “support” 

in a general sense. Taylor is the basis of hundreds if not thousands of arguments that one or another state law is a mismatch for one or another federal statute. (Just look at the number of decisions that the Supreme Court and the courts of appeals have rendered since 1990 applying the “categorical” 

and “modified categorical” approaches. A search by computer turns up 197 for the Seventh Circuit alone, and that 

search was limited to decisions that cite Taylor rather than one 

of its successors.) What a lawyer needs to know is whether a
No. 22-1678 23 

particular “categorical” argument has reasonable prospects—

and in 2014 competent lawyers would not have rated the positional-isomer argument high on that list.

This discussion of “support” is parallel to the question 

whether a particular legal rule has been clearly established. 

The Justices say often that, to overcome qualified immunity, 

the rule must be established concretely, as applied to a situation, rather than at a high level of generality. See, e.g., White 

v. Pauly, 580 U.S. 73 (2017); Mullenix v. Luna, 577 U.S. 7 (2015). 

The same proposition holds for the law of ineffective assistance. Taylor supplies support at a high level of generality for 

many inquiries into whether a state law is a match for a particular federal law, but it takes a decision such as Ruth to apply this principle so concretely that all reasonable lawyers 

must try to take advantage.

What fraction of criminal defense lawyers in 2014 investigated the possibility that a state statute’s mention of positional isomers would prevent use of a state conviction in recidivist sentencing? I’ll hazard a guess that less than 1% did 

so (for if even 1% made such an argument, starting soon after 

Taylor, the holding of Ruth would have come decades earlier). 

Can it really be that 99% of all criminal defense lawyers are in 

the bottom 10% of the profession? If “prevailing professional 

norms” govern, then a lawyer who does or omits what almost 

every other lawyer at the time does or omits satisfies the constitutional standard. That’s what Strickland tells us. Only the 

distorting effect of hindsight could lead to a contrary conclusion.