Frederick Coleman v. United States

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 sen-

tenced 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 fel-

ony drug offenses. After we denied his direct appeal, Cole-

man 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 plead-

ing. Because the district court abused its discretion in reach-

ing that conclusion, we reverse and remand for further pro-

ceedings 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. Pursu-

ant 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 convic-

tions 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 sen-

tence pursuant to 28 U.S.C. § 2255. Coleman’s § 2255 motion

asserted, among other things, that his appointed counsel, An-

thony Vaupel, was ineffective for having failed to inform him

of the government’s pretrial 21 U.S.C. § 851 Notice of En-

hancement. This notice informed Coleman that, should he be

1 The First Step Act of 2018, enacted after Coleman’s sentencing, re-

duced the mandatory minimum sentences from life to 25 years’ imprison-

ment 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). Ac-

cording 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 en-

tered 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 Cole-

man on more than one occasion that he faced, and would re-

ceive, a mandatory life sentence if found guilty. Vaupel also

attested that he had told Coleman that the mandatory life sen-

tence 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 mo-

tion, Coleman moved, again pro se, to amend it pursuant to

Federal Rule of Civil Procedure 15(c). His amendment con-

tained 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 of-

fenses” under § 841(b)(1)(A) given that Illinois defined “co-

caine” 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 be-

cause “the claims rest[ed] on distinct types of attorney misfea-

sance 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 ap-

pealed, 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 inef-

fective 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 col-

league Katherine Stallings Bailey of Winston & Strawn LLP, for their ad-

vocacy 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 constitution-

ally 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 as-

sistance of counsel claim, however, we must resolve two pre-

liminary questions. First, we must determine whether appel-

late 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 dis-

cretion. 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 mo-

tion.

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 stand-

ard,” 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 pro-

vision of Rule 15(c), which allows such amendment if it “as-

serts a claim or defense that arose out of the conduct, transac-

tion, 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 dis-

cretion. 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 re-

view “includes de novo review of the legal basis for the futil-

ity”). 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). In-

deed, 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 Arre-

ola 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 be-

fore 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 ques-

tion. Compare United States v. Ciampi, 419 F.3d 20, 23 (1st Cir. 2005) (apply-

ing 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 occur-

rence 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 cir-

cumstances 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 defend-

ant enough notice of the nature and scope of the plaintiff’s

claim that he shouldn’t have been surprised by the amplifica-

tion 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 Cro-

ciere S. p. A., 560 U.S. 538, 550 (2010) (explaining that the pur-

pose of relation back is “to balance the interests of the defend-

ant 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 mer-

its”).

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 the-

ory 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 oth-

ers, 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 peti-

tioner initially claimed that admission of videotaped testi-

mony from a prosecution witness violated the Sixth Amend-

ment’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 dis-

trict 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 “im-

merse courts in case-specific factual issues” we typically re-

view 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 con-

cluded that at no time prior to the plaintiffs’ proposed amend-

ment 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 un-

der which we reviewed the district court’s decision, when re-

viewing mixed questions of fact and law, the standard turns

on “which ‘judicial actor is better positioned’ to make the de-

cision.” 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 “relation-

back” 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 circum-

stances of a particular case, our review of a district court’s ap-

plication 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 to-

day, it is not difficult for us to conclude that, in this case, the

district court abused its discretion in denying Coleman’s mo-

tion 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 ‘signif-

icant’ changes to a complaint … can relate back so long as the

defendant had fair notice of the substance of the new allega-

tions from the outset.” Supreme Auto, 902 F.3d at 741.

Construing Coleman’s original pro se § 2255 petition liber-

ally, 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 gov-

ernment 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 dif-

ferent facts,” and therefore the amendment did not relate

back. Id. In the district court’s view, “[w]hile the original pe-

tition contained a claim centered on an alleged failure to in-

form 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, particu-

larly 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 no-

tice and the adequacy of advice he provided to Coleman as to

the impact the notice may have had on the case. This com-

monality is enough to unite the claims.

We also fail to see how the government could have reason-

ably been surprised by Coleman’s amended claim. The gov-

ernment no doubt encounters countless pro se filings such as

No. 22-1678 13

this and knows that they must be construed liberally. Cole-

man’s allegations that his attorney had inadequately coun-

seled 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 par-

ties 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 govern-

ment 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 Cole-

man’s amended claims. Accordingly, on balance, any preju-

dice 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 Pro-

cedure in general, and Rule 15 in particular, for resolving dis-

putes on their merits.” Krupski, 560 U.S. at 550.

We therefore find that the district court abused its discre-

tion in determining that Coleman’s amended § 2255 pleading

did not relate back to his original motion. Finding that Cole-

man’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 re-

lief on his claim unless he can establish that (1) his attorney’s

“performance was deficient” and (2) “the deficient perfor-

mance prejudiced the defense.” 466 U.S. at 687.

14 No. 22-1678

1. Performance

We begin by considering whether defense counsel’s fail-

ure 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.” Har-

ris 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, Cole-

man 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 rea-

sonableness 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 circum-

stances where [defense counsel] may be obliged to make, or

at least to evaluate, an argument that is sufficiently foreshad-

owed 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 Il-

linois 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-estab-

lished.”) (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 pred-

icate offenses in other contexts. See, e.g., Descamps v. United

States, 570 U.S. 254, 264–65 (2013) (concluding that a Califor-

nia 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 metham-

phetamine while federal law “punishe[d] the possession of

optical isomers alone”); Samas v. United States, No. 3:10-CV-

422 (JCH), 2011 WL 221866, at *4 (D. Conn. Jan. 20, 2011) (con-

cluding that § 2255 petitioner’s state conviction was not a “fel-

ony drug offense” because two analogs of fentanyl criminal-

ized 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 ap-

plied to prior convictions like Coleman’s by 2014, the frame-

work 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 predi-

cate 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 Su-

preme 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 vi-

ability 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 un-

persuaded 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 applica-

tion of the categorical approach to drug isomers is “not com-

plex.” 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 sen-

tence 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 chal-

lenge.

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

to compare the plain language of the statutes” to determine if the predi-

cate 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 cred-

ible strategic reasons for not raising it, that would be a differ-

ent 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 con-

sider 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)). Cole-

man has met his burden.

We have held that, in cases where a court relies on an in-

correctly calculated Guidelines range to sentence a defendant,

a reasonable probability of prejudice is presumed absent un-

usual circumstances. Bridges, 991 F.3d at 808–09 (citing Mo-

lina-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 applica-

ble 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 probabil-

ity of prejudice does not exist,” such as when the record

shows that the district court would have given the same sen-

tence in any event. 578 U.S. at 200. Only in these “unusual cir-

cumstances,” 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 statuto-

rily 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 ap-

peal, are sufficient to support application of the presumption

here. 10 As Coleman observes, absent the district court’s appli-

cation of the § 851 enhancement, he would not have been sub-

ject to a mandatory life sentence and the district court would

have had discretion to sentence him after full and fair consid-

eration 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 con-

sider[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 deter-

mination that Coleman’s amended § 2255 motion did not re-

late 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 enter-

tained the petition as amended. But I do not think that a re-

mand 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 Illi-

nois do not count toward federal recidivist sentencing. (Illi-

nois defines as cocaine the products of coca leaves, including

optical, positional, and geometric isomers; federal law men-

tions 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 succes-

sors, 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 treat-

ing as ineffective assistance a lawyer’s failure to make a Ruth-

like 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 ob-

serve (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 rep-

resenting criminal defendants have dozens of potentially im-

portant 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 pro-

ductive, a reasonable attorney uses as cues what has been pro-

ductive. The number of potential lines of investigation and ar-

gument 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 reason-

able 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 de-

fense after it has proved unsuccessful, to con-

clude 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 rea-

sonable 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 sup-

port at a high level of generality, then every lawyer must in-

vestigate every argument, for every argument has “support”

in a general sense. Taylor is the basis of hundreds if not thou-

sands of arguments that one or another state law is a mis-

match for one or another federal statute. (Just look at the num-

ber of decisions that the Supreme Court and the courts of ap-

peals have rendered since 1990 applying the “categorical”

and “modified categorical” approaches. A search by com-

puter 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 po-

sitional-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 situa-

tion, 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 assis-

tance. Taylor supplies support at a high level of generality for

many inquiries into whether a state law is a match for a par-

ticular federal law, but it takes a decision such as Ruth to ap-

ply this principle so concretely that all reasonable lawyers

must try to take advantage.

What fraction of criminal defense lawyers in 2014 investi-

gated the possibility that a state statute’s mention of posi-

tional isomers would prevent use of a state conviction in re-

cidivist 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 con-

stitutional standard. That’s what Strickland tells us. Only the

distorting effect of hindsight could lead to a contrary conclu-

sion.