Jeffery Bridges v. United States

In the

United States Court of Appeals

For the Seventh Circuit

____________________

No. 20-1623

JEFFERY BRIDGES,

Petitioner-Appellant,

v.

UNITED STATES OF AMERICA,

Respondent-Appellee.

____________________

Appeal from the United States District Court for the

Southern District of Indiana, Indianapolis Division.

No. 1:19-cv-00550-TWP-DLP — Tanya Walton Pratt, Judge.

____________________

ARGUED DECEMBER 11, 2020 — DECIDED MARCH 17, 2021

____________________

Before ROVNER, HAMILTON, and SCUDDER, Circuit Judges.

HAMILTON, Circuit Judge. This appeal raises fundamental

questions about what is expected of defense counsel in the

federal criminal justice system, where almost all defendants

plead guilty. Counsel must negotiate guilty pleas and argue

for more lenient sentences, both of which require expert

knowledge of the federal Sentencing Guidelines. This

knowledge is a core competency for federal criminal defense.

2 No. 20-1623

The issue here is whether a lawyer’s failure to raise an im-

portant and, in this case, ultimately meritorious guideline ar-

gument may constitute ineffective assistance of counsel even

where there was no directly on-point precedent within the cir-

cuit at the relevant time. We find that it may in this case.

Now in his sixties, petitioner Jeffery Bridges has been in

and out of prison since he was a teenager and has been bat-

tling drug addiction even longer. After staying out of trouble

for eight years, Bridges got involved in drugs again and com-

mitted four robberies in two days in March 2017. He netted

scarcely $700 in total and was easily caught by the police. A

federal grand jury indicted Bridges for four counts of robbery

in violation of the Hobbs Act, 18 U.S.C. § 1951.

Bridges agreed to a guilty plea stipulating that he was sub-

ject to the guideline career offender enhancement, U.S.S.G.

§ 4B1.1, which could apply only if his crimes of conviction

were “crimes of violence” as defined by the Guidelines. This

enhancement more than doubled his advisory guideline sen-

tencing range. The district court imposed a below-guideline

sentence of 140 months. Bridges did not appeal. He had

waived that right in his plea deal.

Bridges now seeks postconviction relief under 28 U.S.C.

§ 2255, alleging he was denied effective assistance of counsel

in pleading guilty. He argues that his lawyer failed to realize

and argue that Hobbs Act robbery did not then qualify as a

“crime of violence” under the Guidelines, so he should not

have been categorized as a career offender. When Bridges

pleaded guilty and was sentenced, there was no binding prec-

edent in this circuit on this issue. Bridges argues that compe-

tent counsel still would have recognized the issue or at least

No. 20-1623 3

known to investigate it. The district court denied relief with-

out holding a hearing, reasoning that counsel’s failure to an-

ticipate arguments that we have not yet accepted cannot be

constitutionally deficient.

We reverse for an evidentiary hearing on defense coun-

sel’s performance under 28 U.S.C. § 2255(b). First, we join the

other circuits that have concluded that Hobbs Act robbery is

not a “crime of violence” as that phrase is currently defined

in the Guidelines. Although we had not so ruled when

Bridges pleaded guilty, the building blocks for a successful

legal argument were already in place. Effective counsel would

have considered this question that was so important in this

case. At that time, minimal research would have uncovered a

Tenth Circuit decision squarely holding that Hobbs Act rob-

bery was no longer a crime of violence under a 2016 amend-

ment to the guideline definition of a crime of violence.

We realize how counterintuitive it is to argue or hold that

Hobbs Act robbery is not a crime of violence—and that coun-

sel could be deficient for failing to argue for that unexpected

result. Yet defense lawyers, prosecutors, and judges in the fed-

eral system all appreciate that both statutory and guideline

sentencing enhancements for recidivism and crimes of vio-

lence have produced many counterintuitive results over the

last several decades. During those years, both federal statutes

and the Sentencing Guidelines have used the “categorical

method” to classify prior convictions and current offenses.

The Sentencing Commission proposed guideline amend-

ments in 2018 to reduce reliance on the categorical method. 83

Fed. Reg. 65400, 65407–65412 (Dec. 20, 2018). The Commis-

sion has been unable to act on those proposed amendments,

4 No. 20-1623

though, because it has lacked a quorum for years. Bridges

may be a beneficiary of that odd circumstance.

I. Factual and Procedural Background

Over two days in March 2017, Bridges robbed four retail

stores in Indianapolis. In three, he held his hand in a pocket

in the shape of a gun. In the fourth, he threatened to “hurt”

the cashier if his demands were not met. Bridges netted a total

of $719.35.

Police quickly identified Bridges as a suspect. Five days

after the last robbery, Bridges was stopped by police and ad-

mitted that he had committed the robberies. A federal grand

jury indicted him on four counts of robbery in violation of the

Hobbs Act, 18 U.S.C. § 1951(a).

Bridges pleaded guilty to all four robberies. His plea

agreement stipulated to certain guideline calculations, includ-

ing application of the career offender enhancement in § 4B1.1.

This enhancement applies when a defendant with a sufficient

history of violent or drug convictions is sentenced for a new

“controlled substances offense” or “crime of violence.”

Bridges’ plea stipulated that this enhancement applied based

on two prior convictions for robbery in state court and as-

sumed that his new Hobbs Act robbery convictions also

counted as crimes of violence. The plea agreement was final-

ized on April 24, 2018. On July 31, 2018, he pleaded guilty in

court and was sentenced on the same day.

At sentencing and after accounting for Bridges’ acceptance

of responsibility, his guideline offense level was 29, with crim-

inal history VI as a career offender, for a range of 151 to 188

No. 20-1623 5

months. Without the career offender guideline, Bridges’ advi-

sory range would likely have been 57 to 71 months, based on

offense level 21 and criminal history category IV.

Defense counsel did not challenge the guideline calcula-

tions. Instead, counsel focused on mitigation arguments.

Bridges, he told the court, had had a difficult life and was try-

ing to improve himself to help his family. Bridges was more

or less abandoned by his parents and subjected to physical,

emotional, and sexual abuse by family members. His drug

problems, which he blames for the 2017 robberies, began be-

fore he was even thirteen years old. Defense counsel argued

that despite these challenges, Bridges continued to try to bet-

ter himself through treatment and education, and suggested

that his age made him unlikely to commit future offenses.

Bridges asked for a below-guideline 108-month sentence. The

government asked for a 160-month sentence.

The district court accepted the agreed guideline calcula-

tions putting the advisory range at 151 to 188 months. The

court dismissed out of hand the aging-out-of-crime argument.

After all, Bridges had committed these robberies in his sixties.

Bridges also had a long history of violent crime, including a

now 45-year-old conviction for participating in a home inva-

sion and rape and robbery, and he had shown dangerous

tendencies and disrespect for the law and others. Other miti-

gation arguments had some weight. The judge explained that

the final sentence was below the guideline range because of

Bridges’ experiences as a child and his continuing efforts at

rehabilitation. The court sentenced Bridges a little below the

low end of the guideline range, to 140 months in prison.

Pursuant to his plea deal, Bridges did not appeal directly.

Instead, he brings this suit under the federal habeas corpus

6 No. 20-1623

statute, 28 U.S.C. § 2255. His only path to challenge his sen-

tence and avoid his waiver of his right to appeal is to argue

that his lawyer was ineffective in negotiating the plea agree-

ment with the career offender enhancement. Bridges argues

that Hobbs Act robbery is not a crime of violence as the Guide-

lines now define that phrase and that his counsel should have

recognized as much. Without holding an evidentiary hearing,

the district court denied relief, reasoning that even if Hobbs

Act robbery is not a crime of violence, there was no binding

circuit precedent on that issue and that the Sixth Amendment

does not require defense counsel to anticipate future develop-

ments in case law.

II. Legal Standard

The federal habeas statute permits a prisoner to petition

for relief “upon the ground that the sentence was imposed in

violation of the Constitution or laws of the United States.” 28

U.S.C. § 2255(a). The trial court must “grant a prompt hear-

ing” on the petition unless the motion and record “conclu-

sively show that the prisoner is entitled to no relief.”

§ 2255(b). When reviewing the denial of a federal prisoner’s

§ 2255 petition, we review the district court’s legal conclu-

sions de novo, its factual findings for clear error, and its deci-

sion to deny an evidentiary hearing for abuse of discretion.

Martin v. United States, 789 F.3d 703, 705 (7th Cir. 2015). A de-

cision that rests on an error of law is always an abuse of dis-

cretion. Id. at 706.

III. Hobbs Act Robbery Is Not a Guidelines “Crime of Violence”

The career offender guideline applies here only if an of-

fense of a conviction is a “crime of violence” as defined in the

Guidelines. See U.S.S.G. §§ 4B1.1; 4B1.2. Before 2015, there

No. 20-1623 7

would have been no doubt that Hobbs Act robbery was a

crime of violence. That year, however, the Supreme Court de-

cided Johnson v. United States, 576 U.S. 591 (2015), which held

that the so-called residual clause in the statutory definition of

a “violent felony” in 18 U.S.C. § 924(e)(2)(B) was unconstitu-

tionally vague. In response to uncertainty about whether John-

son would apply to the similar—but advisory—definition in

the Sentencing Guidelines, the U.S. Sentencing Commission

amended the guideline definition of “crime of violence” to re-

move the similar residual clause and otherwise narrow its

scope. See Guidelines Amendment 798; U.S.S.G. § 4B1.2 (as

amended August 1, 2016). 1

The new definition, which applied to Bridges, provides:

The term “crime of violence” means any offense

under federal or state law, punishable by im-

prisonment for a term exceeding one year,

that—

(1) has as an element the use, attempted use, or

threatened use of physical force against the per-

son of another, or

(2) is murder, voluntary manslaughter, kidnap-

ping, aggravated assault, a forcible sex offense,

robbery, arson, extortion, or the use or unlawful

possession of a firearm described in 26 U.S.C.

1 In Beckles v. United States, 137 S. Ct. 886 (2017) the Supreme Court

held that the nearly identical residual clause in the Guidelines before

Amendment 798 was not unconstitutionally vague for defendants sen-

tenced under the advisory Guideline regime. The Court reasoned that the

advisory character of the Guidelines removed the residual clause in the

definition from the void-for-vagueness doctrine applied in Johnson.

8 No. 20-1623

§ 5845(a) or explosive material as defined in 18

U.S.C. § 841(c).

Even though Hobbs Act robbery is one of the two most

common federal robbery crimes (the other is bank robbery

under 18 U.S.C. § 2113), it does not qualify as “robbery”

within the meaning of the new guideline definition of crimes

of violence. The heart of the problem is that a person may

commit Hobbs Act robbery by threatening physical violence

against any “person or property.” 18 U.S.C. § 1951(b)(1). The

guideline definition of robbery is narrower, as it is understood

to require a threat of physical violence against a person. A

threat to property does not count. Under the categorical

method used to decide such questions, the broader definition

of Hobbs Act robbery means that it does not count as “rob-

bery” under Guideline Amendment 798.

Following Amendment 798, every federal appellate court

to address the issue squarely has concluded that Hobbs Act

robbery does not fall within the narrow definition of “crime

of violence” in Amendment 798 and codified in § 4B1.2.

United States v. O’Connor, 874 F.3d 1147 (10th Cir. 2017);

United States v. Camp, 903 F.3d 594 (6th Cir. 2018); United States

v. Eason, 953 F.3d 1184 (11th Cir. 2020); see also United States v.

Rodriguez, 770 F. App’x 18 (3d Cir. 2019) (non-precedential);

United States v. Edling, 895 F.3d 1153 (9th Cir. 2018) (recogniz-

ing impact of Amendment 798 on similar Nevada robbery

statute); but see United States v. Andrews, 768 F. App’x 189 (5th

Cir. 2019) (non-precedential) (declining to revisit prior circuit

precedent regarding a similar California robbery statute after

Amendment 798). We may summarize our colleagues’ careful

and persuasive analysis of the issue.

No. 20-1623 9

In determining whether an offense of conviction, here

Hobbs Act robbery, qualifies as a crime of violence under the

Guidelines, we use the so-called categorical approach. United

States v. Campbell, 865 F.3d 853, 855 (7th Cir. 2017); see gener-

ally Camp, 903 F.3d at 599. Under the categorical approach,

which also applies to the Armed Career Criminal Act, see 18

U.S.C. § 924(e), sentencing courts may look only to the statu-

tory definitions—i.e., the elements—of a defendant’s offenses,

and not to the actual facts underlying those convictions.

Descamps v. United States, 570 U.S. 254, 261 (2013). The cate-

gorical method presumes that a conviction rests on the least

serious acts that would satisfy the statute, regardless of the

offender’s actual conduct. Campbell, 856 F.3d at 856, citing

Johnson v. United States, 559 U.S. 133, 137 (2010).

If Hobbs Act robbery can be committed in a way that falls

outside the definition of a “crime of violence” in U.S.S.G.

§ 4B1.2, then it is not a categorical fit, regardless of how the

defendant actually committed his robberies. The Hobbs Act

criminalizes a broad range of criminal behavior under the

“robbery” banner:

The term ‘robbery’ means the unlawful taking

or obtaining of personal property from the per-

son or in the presence of another, against his

will, by means of actual or threatened force, or

violence, or fear of injury, immediate or future,

to his person or property, or property in his cus-

tody or possession, or the person or property of a

relative or member of his family or of anyone in

his company at the time of the taking or obtain-

ing.

18 U.S.C. § 1951(b)(1) (emphases added).

10 No. 20-1623

The phrase “crime of violence” is defined in § 4B1.2 in two

ways. The first is where the offense “has as an element the use,

attempted use, or threatened use of physical force against the

person of another.” Hobbs Act robbery does not satisfy this

first alternative under the guideline definition because a use

of force or a threat of force against property is sufficient. 2

The second part of the definition lists a number of crimes:

“murder, voluntary manslaughter, kidnapping, aggravated

assault, a forcible sex offense, robbery, arson, extortion, or the

use or unlawful possession” of a machine gun or explosive.

§ 4B1.2(a)(2). We focus here on whether Hobbs Act robbery is

a categorical fit for guideline robbery or extortion.

The application notes to § 4B1.2 do not define robbery, so

we turn to the “generic” definition of the crime. Klikno v.

United States, 928 F.3d 539, 542 (7th Cir. 2019), quoting

Descamps, 570 U.S. at 257. The generic definition of robbery

does not include threats of force against property. O’Connor,

874 F.3d at 1154–55 (collecting cases, discussing the approach

of “a significant majority of states,” and reviewing criminal

law treatises); accord Camp, 903 F.3d at 601–02 (generic rob-

bery includes “the requirement that the danger be both im-

mediate and to a person”) (emphasis added); Eason, 953 F.3d at

2Note that 18 U.S.C. § 924(c)(3) and U.S.S.G. § 4B1.2 define “crime of

violence” differently. Camp, 903 F.3d at 597. Under § 924(c)(3)(A), a crime

of violence encompasses crimes that have “as an element the use, at-

tempted use, or threatened use of physical force against the person or prop-

erty of another.” (emphasis added). Thus, nothing in this decision disturbs

our cases holding that Hobbs Act robbery is a crime of violence for statutes

that use the “or property” definition. See, e.g., United States v. Rivera, 847

F.3d 847, 848 (7th Cir. 2017).

No. 20-1623 11

1193–94; see also Klikno, 928 F.3d at 544–47, discussing Stokel-

ing v. United States, 139 S. Ct. 544, 552 (2019) (recognizing that

generic robbery is distinct from larceny in that it requires

“force that overcomes a victim’s resistance”); Shabazz v.

United States, 912 F.3d 73, 77 (2d Cir. 2019) (“Scholars of the

criminal law underline the inherent potential for physical harm

to the victim as the explanation why robbery developed as, and

continues to be treated as, an aggravated felony, generally

carrying harsher punishments than other forms of larceny.”)

(emphasis added). Hobbs Act robbery is not a categorical

match for generic robbery because it can be committed

through threats against property.

The government has suggested that a Hobbs Act robbery

that threatens only property might still qualify as extortion in

the Guideline’s list of enumerated crimes of violence, trigger-

ing the career offender enhancement. The application notes

define extortion as “obtaining something of value from an-

other by the wrongful use of (A) force, (B) fear of physical in-

jury, or (C) threat of physical injury.” U.S.S.G. § 4B1.2, cmt. 1.

The central issue here is whether fear or threat of “physical

injury” could fit the Hobbs Act robbery branch allowing con-

viction for harm or threats to property. That depends on how

broadly “physical injury” is defined. The government argues

that “threat of physical injury” means any threat to harm a

physical object, be it animal, vegetable, or mineral. Bridges

counters that “physical injury” simply means injury to a per-

son.

We agree with our colleagues in other circuits who have

rejected the government’s argument. Extortion does not fill

the categorical gaps for Hobbs Act robbery because the

Guidelines use “physical injury” to mean injury to a person.

12 No. 20-1623

As the Tenth Circuit explained in O’Connor: “The Guidelines

contain several examples where ‘physical injury’ is distin-

guished from property damage or where the phrase clearly

refers to injury to a person.” 874 F.3d at 1157 & n.17, discuss-

ing U.S.S.G. §§ 5K2.2, 2C1.1(c)(3), 2J1.2(b)(1)(B), and 5K2.12.

Moreover, the common meaning of the phrase “physical in-

jury” is “bodily injury.” Injury, Black’s Law Dictionary (11th

ed. 2019) (defining “physical injury” as “bodily injury,” that

is, “physical damage to a person’s body”); O’Connor, 874 F.3d

at 1157 (quoting 10th edition of Black’s); accord Eason, 953

F.3d at 1194; Camp, 903 F.3d at 603. Hobbs Act robbery thus

extends more widely than guideline extortion.

The government argues next that this definition of “extor-

tion” must be wrong because it would be redundant, overlap-

ping completely with generic robbery. We are not persuaded.

The two are not identical. Generic robbery requires that the

threat of violence be imminent; guideline extortion does not.

See Camp, 903 F.3d at 601 (discussing immediacy requirement

of generic robbery). In addition, a textual argument based on

avoiding redundancy is not necessarily a show-stopper, as

“the presence of some redundance is rarely fatal on its own to

a statutory reading.” White v. United Airlines, 987 F.3d 616, 622

(7th Cir. 2021). We have accordingly cautioned that drafters

of legal documents may “intentionally err on the side of re-

dundancy to ‘capture the universe.’” See Sterling National

Bank v. Block, 984 F.3d 1210, 1218 (7th Cir. 2021), quoting Abbe

R. Gluck & Lisa Schultz Bressman, Statutory Interpretation from

the Inside—an Empirical Study of Congressional Drafting, Delega-

tion, and the Canons: Part I, 65 Stan. L. Rev. 901, 934 (2013).

In sum, Hobbs Act robbery criminalizes threats against

property, and both generic robbery and guideline extortion

No. 20-1623 13

reach only threats against persons. Hobbs Act robbery is not

a categorical fit, so Bridges was not convicted of a crime of

violence as the Guidelines define the phrase. The career of-

fender guideline should not have been applied.

IV. Effective Assistance of Counsel

For Bridges, it is not enough to show that a challenge to

the career offender enhancement should have prevailed. The

issue is whether his defense lawyer failed to provide effective

assistance of counsel in 2018 by stipulating to the enhance-

ment as part of the plea agreement rather than objecting to it.

The government argues that counsel’s performance did

not fall below the constitutional threshold because all this

hair-splitting under the categorical approach is so convoluted

and counterintuitive. Competent counsel, according to the

government, need not ask and answer legal koans, such as

when is a robbery not a robbery? Indeed, federal defenders in

this circuit did not regularly raise this argument until well af-

ter Bridges was sentenced. Bridges counters that the categor-

ical approach is a well-known tool in applying the Guidelines,

and as categorical approach cases go, this analysis is straight-

forward. He also asserts that counsel should have been on the

lookout for categorical approach problems given the recent

Amendment 798, the dramatic impact of this factor on his

guideline range, and cases around the country where counsel

did recognize and raise these arguments. We conclude that

under these facts Bridges is at least entitled to a hearing.

The Sixth Amendment right to counsel applies during plea

negotiations. E.g., Lafler v. Cooper, 566 U.S. 156, 162 (2012). We

use the familiar two-part Strickland v. Washington test to deter-

14 No. 20-1623

mine whether counsel’s performance fell below the constitu-

tional minimum. 466 U.S. 668 (1984). Under this rubric, coun-

sel was ineffective if both “counsel’s performance was defi-

cient” and “the deficient performance prejudiced the de-

fense.” Id. at 687. The performance issue is whether “counsel

made errors so serious that counsel was not functioning as the

‘counsel’ guaranteed the defendant by the Sixth Amend-

ment.” Id.

A. Performance

Bridges is entitled to a hearing unless the record and mo-

tion “conclusively show that [he] is entitled to no relief.” 28

U.S.C. § 2255(b). The district court reasoned that the lack of

controlling precedent in this circuit defeated Bridges’ Sixth

Amendment argument. We respectfully disagree. In some cir-

cumstances, defense counsel may be required to anticipate ar-

guments foreshadowed but not yet adopted by existing case

law. Based on the timeline and allegations in the petition, we

cannot say that this claim is conclusively foreclosed. Bridges

is entitled to try to prove his allegations at a hearing.

We apply an objective standard of reasonableness consid-

ering all the circumstances. Hinton v. Alabama, 571 U.S. 263,

272–73 (2014). Deference must be given to counsel’s strategic

decisions, but “strategic choices made after less than complete

investigation [of law and facts] are reasonable precisely to the

extent that reasonable professional judgments support the

limitations on investigation. In other words, counsel has a

duty to make reasonable investigations or to make a reasona-

ble decision that makes particular investigations unneces-

sary.” Id. at 274, quoting Strickland, 466 U.S. at 690–91. “In the

plea bargaining context, reasonably competent counsel will

attempt to learn all of the facts of the case, make an estimate

No. 20-1623 15

of a likely sentence, and communicate the results of that anal-

ysis before allowing his client to plead guilty.” Gaylord v.

United States, 829 F.3d 500, 506 (7th Cir. 2016) (quotation omit-

ted); see also Anderson v. United States, 981 F.3d 565, 575–76

(7th Cir. 2020) (remanding habeas petition for evidentiary

hearing where counsel’s failure to investigate one available

theory of defense before negotiating plea deal could consti-

tute deficient performance).

“An attorney’s ignorance of a point of law that is funda-

mental to his case combined with his failure to perform basic

research on that point is a quintessential example of unrea-

sonable performance under Strickland.” Hinton, 571 U.S. at 274

(describing examples); see Osagiede v. United States, 543 F.3d

399, 409 (7th Cir. 2008) (“All lawyers that represent criminal

defendants are expected to know the laws applicable to their

client’s defense,” and where “simple computer research”

would turn up those laws, counsel is ineffective for failing to

rely on them absent a strategic justification) (cleaned up); see

also Cates v. United States, 882 F.3d 731, 736 (7th Cir. 2018)

(“[A] mistake of law is deficient performance.”).

Defense attorneys, it is true, are generally not obliged to

anticipate changes in the law. E.g., Valenzuela v. United States,

261 F.3d 694, 700 (7th Cir. 2001). Yet there are some circum-

stances where they may be obliged to make, or at least to eval-

uate, an argument that is sufficiently foreshadowed in exist-

ing case law. Shaw v. Wilson, 721 F.3d 908, 917 (7th Cir. 2013);

see also United States v. Carthorne, 878 F.3d 458, 465–66 (4th

Cir. 2017) (“[T]he ineffective assistance standard may require

16 No. 20-1623

that counsel raise material issues even in the absence of deci-

sive precedent.”), citing Ramirez v. United States, 799 F.3d 845,

855 (7th Cir. 2015).3

If proved, counsel’s apparent failure to investigate or raise

a challenge to the career offender enhancement here could be

deemed to have been deficient performance. There was no

binding in-circuit precedent on this exact issue, but case law

sufficiently foreshadowed this argument, which had been

brought to the forefront by both a recent amendment to the

Guidelines and several court of appeals decisions interpreting

Amendment 798. Bridges is entitled to a “prompt” hearing to

prove his allegations. 28 U.S.C. § 2255(b).

When Bridges was pleading guilty and being sentenced,

the categorical approach was of course well-established. See

generally Taylor v. United States, 495 U.S. 575 (1990). So was its

applicability to the Guidelines. E.g., United States v. Woods,

576 F.3d 400, 403 (7th Cir. 2009) (“In deciding whether a crime

fits [U.S.S.G. § 4B1.2’s definition of crime of violence], the Su-

preme Court has instructed lower courts to use a categorical

3 The requirement that counsel raise issues foreshadowed but not ex-

plicitly resolved by precedent distinguishes the ineffective assistance of

counsel inquiry from plain-error review. “Plain error review by appellate

courts is used to correct only particularly egregious errors by a trial court.

By comparison, the ineffective assistance inquiry on collateral review does

not involve the correction of an error by the district court, but focuses

more broadly on the duty of counsel to raise critical issues for that court’s

consideration.” Carthorne, 878 F.3d at 465 (cleaned up), citing, among other

cases, United States v. Dowell, 388 F.3d 254, 256 (7th Cir. 2004). Accordingly,

our analysis here does not control direct appeals arguing that application

of the career offender enhancement to defendants convicted of Hobbs Act

robbery amounted to a “plain error.”

No. 20-1623 17

approach.”). The overwhelming majority of federal defend-

ants plead guilty. Administrative Office of U.S. Courts, Statis-

tical Tables for the Federal Judiciary, Table D-4 (Dec. 31, 2018)

(89.9% of federal criminal cases end in guilty plea). And the

Guidelines remain the “lodestar” of federal sentencing. Mo-

lina-Martinez v. United States, 136 S. Ct. 1338, 1346 (2016). Sen-

tencing advocacy, both during plea negotiations and before a

district court, is in most cases the most important task of a

federal criminal defender. Understanding how to interpret

the Guidelines and making guideline arguments are core

competencies of federal defense counsel.

Competent counsel would also know that the categorical

approach frequently produces counterintuitive results and

has been the subject of much judicial handwringing. See Amit

Jain & Phillip Dane Warren, An Ode to the Categorical Approach,

67 U.C.L.A. L. Rev. Disc. 132, 134 (2019) (collecting colorful

criticisms before defending categorical approach on the mer-

its). Many of these criticisms acknowledge that the categorical

approach frequently benefits defendants. For example, Judge

Wilkinson has decried it as “a protracted ruse for paradoxi-

cally finding even the worst and most violent offenses not to

constitute crimes of violence.” United States v. Doctor, 842 F.3d

306, 313 (4th Cir. 2016) (Wilkinson, J., concurring). The need

to investigate whether Bridges had a viable categorical ap-

proach argument was especially pronounced in this case be-

cause the Sentencing Commission had narrowed its definition

of “crime of violence” months before Bridges committed these

robberies, and the enhancement nearly tripled the advisory

sentencing range. That effect made this a crucial issue to in-

vestigate. United States v. Winstead, 890 F.3d 1082, 1089 (D.C.

Cir. 2018); see also Wilson v. Gaetz, 608 F.3d 347, 352 (7th Cir.

2010) (“Especially because of the severity of the penalty that

18 No. 20-1623

[defendant] was facing, [counsel] should have done more.”).

Reasonable counsel would investigate such a new and timely

issue, known to benefit criminal defendants, especially con-

sidering the dramatic effect on the guideline range.

We have previously found that counsel’s failure to com-

pare statutory definitions in resolving a guideline question

during plea negotiations would, if proven, constitute deficient

performance. In Brock-Miller v. United States, 887 F.3d 298,

309–10 (7th Cir. 2018), we remanded for a hearing on allega-

tions of deficient performance. We rejected the government’s

argument that examining the “statute to determine if it met

the federal definition of felony drug offense” was too “sophis-

ticated” and “convoluted” to expect from defense counsel. Id.

at 310–11. So too here. The categorical approach may be coun-

terintuitive and artificial, but, like other complex factual and

legal inquiries that regularly arise in criminal defense, com-

petent counsel need to understand it and be able to use it. See

Hinton, 571 U.S. at 274; see also, e.g., Dunn v. Jess, 981 F.3d 582,

592–94 (7th Cir. 2020) (deficient performance where counsel

failed to assimilate conflicting medical reports); United

States v. Sepling, 944 F.3d 138, 146–50 (3d Cir. 2019) (deficient

performance where counsel failed both to investigate whether

the probation officer had correctly listed 3,4-Methylenediox-

ymethamphetamine as the appropriate drug analog for

methylone and to debunk the medical research underlying

the Sentencing Commission’s recommendation of a severe

sentence for trafficking either drug); Shaw, 721 F.3d at 917 (de-

ficient performance where counsel failed to argue that state

appellate courts had misunderstood an Indiana Supreme

Court holding about a fine point of state procedural rules). As

in Brock-Miller, if Bridges demonstrates on remand that he en-

tered into the plea agreement based on advice of counsel that

No. 20-1623 19

fell below constitutional standards, the district court should

not hold him to his pleas. 887 F.3d at 310, citing Hurlow v.

United States, 726 F.3d 958, 966–67 (7th Cir. 2013).

With modern methods of legal research, it would not have

taken long in 2018 for counsel to have found the Tenth Circuit

decision holding that Hobbs Act robbery is not a crime of vi-

olence under the 2016 guideline amendment. The Tenth Cir-

cuit published O’Connor months before Bridges signed his

plea agreement. We cannot say that the record “conclusively

shows” that reasonable counsel would not have found this

noteworthy published opinion, one of the few at the time of

Bridges’ plea that considered the effects of Amendment 798.

See Osagiede, 543 F.3d at 409.

O’Connor was not the only federal appellate opinion dis-

cussing the new guideline definition of crime of violence or

the Hobbs Act. In Edling, the Ninth Circuit noted O’Connor in

concluding that guideline extortion does not categorically

match a state robbery statute. 895 F.3d at 1158. Counsel check-

ing citations to O’Connor, the guideline definition of “crime of

violence,” or the phrase “Hobbs Act” would have also found

the Fourth Circuit’s opinion in United States v. McCollum, 885

F.3d 300 (4th Cir. 2018), issued just one month before Bridges

signed his plea agreement. That opinion noted that O’Connor

“analyzed whether Hobbs Act robbery is a crime of violence

under § 4B1.2(a)(2).” Id. at 306 n.6. On the merits, McCollum

applied the categorical method to the new guideline defini-

tion of crime of violence to hold that conspiring to commit

murder in aid of racketeering is not a crime of violence under

§ 4B1.2 as amended. Id. at 303. That prompted a noteworthy

dissent calling for divine guidance and intervention, id. at 310,

314 (Wilkinson, J., dissenting), and a concurrence that would

20 No. 20-1623

have been satisfied with help from Congress, the Supreme

Court, or perhaps the Sentencing Commission. See id. at 309

(Traxler, J., concurring).

The case for ineffective assistance of counsel here appears

to be stronger than other similar cases concluding that failures

to raise new but well-supported arguments were deficient

performance. The most directly analogous case is Cuthbert-

son v. United States, 833 F. App’x 727 (10th Cir. 2020) (non-

precedential), which concerns the same issue—whether coun-

sel was ineffective for failing to recognize that Hobbs Act rob-

bery is not a crime of violence under the amended § 4B1.2 def-

inition. In Cuthbertson, though, the defendant was sentenced

even before O’Connor was issued. The Tenth Circuit still

found counsel’s performance wanting. 833 F. App’x at 733–34.

We need not reach that far here because O’Connor had already

laid out that path when Bridges pleaded guilty and was sen-

tenced.

In that respect, this case is also more straightforward than

United States v. Winstead, in which the D.C. Circuit found

counsel ineffective for failing to raise an administrative law

argument against applying the career offender guideline. 890

F.3d at 1090. Unlike this case, however, there was no out-of-

circuit precedent supporting the criminal defendant’s posi-

tion in Winstead. In fact, all the circuits that had addressed

Winstead’s issue at the time of his sentencing had rejected his

argument. See id. at 1091; see also United States v. Adams, 934

F.3d 720, 728–29 (7th Cir. 2019) (declining to follow Winstead

because of binding circuit precedent). The D.C. Circuit relied,

as we do here, on the fact that the career offender guideline

dramatically increased the advisory sentence, so that the issue

No. 20-1623 21

deserved more attention than counsel had apparently given

it. Winstead, 890 F.3d at 1090.

The government argues here that defense counsel in this

circuit were not raising this issue in 2018, so that Bridges’ law-

yer’s omission of this guideline argument was not objectively

unreasonable. That argument may carry some weight, but we

do not view it as conclusive. Even in the context of “doubly

deferential” review under the Antiterrorism and Effective

Death Penalty Act, see Burt v. Titlow, 571 U.S. 12, 15 (2013); 28

U.S.C. § 2254(d)(1), we have explained that a lawyer’s

“fail[ure] to take advantage of a clear avenue of relief for her

client is no less concerning because many others made the

same error.” Jones v. Zatecky, 917 F.3d 578, 580 (7th Cir. 2019);

see generally Shaw, 721 F.3d at 917 (despite double deference,

appellate counsel’s failure to raise issue under largely mori-

bund state statute was deficient performance where some

counsel and trial courts had recognized the issue and counsel

offered no comparably strong alternative arguments on ap-

peal). We see no reason to hold federal defenders in Indian-

apolis, Chicago, and Milwaukee to a lower standard than

those in Kansas City, Las Vegas, Ann Arbor, and Brooklyn,

who, after all, must apply the same Supreme Court prece-

dents to the same Guidelines Manual. See Shaw, 721 F.3d at

917. 4

4 See United States v. Edling, Case No. 2:15-cr-300 (D. Nev. Sep. 9,

2016), Dkt. 32 at 3–6 (Defendant’s Sentencing Memorandum; arguing that

robbery and coercion were not crimes of violence under amended U.S.S.G.

§ 4B1.2); United States v. Camp, Case No. 2:15-cr-20744 (E.D. Mich. July 11,

2017), Dkt. 38, at 5–15 (July 11, 2017) (United States’ Sentencing Memoran-

dum; responding to defendant’s arguments that categorical approach ex-

cluded some state and federal robbery statutes as crimes of violence);

United States v. Walker, Case No. 1:15-cr-388 (E.D.N.Y. Jan. 12, 2018),

22 No. 20-1623

In this case, the erroneous application of the career of-

fender enhancement almost tripled the low end of the guide-

line range from 57 months to 151 months. Bridges has shown

that counsel’s performance may have been deficient in not

raising this issue, following the recent Amendment 798,

which substantially narrowed the definition of “crime of vio-

lence,” and the well-known counterintuitive and defendant-

friendly results produced by the categorical approach.

Accordingly, the district court’s decision not to hold a

hearing was an abuse of discretion because it rested on the

erroneous legal conclusion that counsel’s failure to anticipate

this career offender argument could not constitute ineffective

assistance of counsel in the absence of controlling circuit prec-

edent. See Brock-Miller, 887 F.3d at 304; Martin, 789 F.3d at 706.

To be clear: we are not holding as a matter of law that counsel

was ineffective. It is possible that defense counsel had a rea-

Dkt. 139 at 4 (Defendant’s Sentencing Memorandum; “The Tenth Circuit

has recently held that robbery under the Hobbs Act is not a crime of vio-

lence under U.S.S.G. § 4B1.2.”); see also United States v. O’Connor, Case

No. 2:15-cr-20079 (D. Kan. May 25, 2016), Dkt. 23 at 10 (Defendant’s Sen-

tencing Memorandum; raising issue under pre-2016 version of § 4B1.2,

though ultimately defendant was sentenced after the effective date of

Amendment 798); United States v. Jones, Case No. 2:15-cr-107 (D. Nev.

Aug. 15, 2016), Dkt. 47 at 2 (Addendum to Defendant’s Sentencing Mem-

orandum; raising categorical approach issue with another aspect of

§ 4B1.2); cf. Gaybor v. United States, 2018 WL 4519200, *7 (D. Ariz. May 9,

2018) (noting O’Connor’s conclusion that U.S.S.G. § 4B1.2(a)(1) is limited

to force against a person and Hobbs Act robbery is not a crime of violence

in its discussion of crimes of violence as defined in 18 U.S.C.

§ 924(c)(3)(A)).

No. 20-1623 23

sonable sentencing strategy that deserves deference. See An-

derson, 981 F.3d at 578 (remanding for hearing); Brock-Miller,

887 F.3d at 311 (same); Osagiede, 543 F.3d at 411 (same).

We must emphasize that “[j]udicial scrutiny of counsel’s

performance must be highly deferential,” as Strickland and its

countless progeny have made clear. 466 U.S. at 689. Strategic

choices made after a thorough investigation are “virtually un-

challengeable.” Id. at 690. Yet deferential review does not

mean no review: a “court adjudicating a Strickland claim can’t

just label a decision ‘strategic’ and thereby immunize it from

constitutional scrutiny.” Jones v. Calloway, 842 F.3d 454, 464

(7th Cir. 2016). In any case, one must evaluate a defense coun-

sel’s performance by considering the other options available.

Compare, e.g., Brock-Miller, 887 F.3d at 302, 311 (remanding

§ 2255 action for hearing where defense counsel had raised

frivolous objection to sentencing enhancement under 21

U.S.C. § 851 but overlooked meritorious objection), with Har-

ris v. United States, 366 F.3d 593, 596 (7th Cir. 2004) (counsel

not deficient for strategically declining to argue for “safety

valve” reduction in guideline range where its applicability

was an open question and pushing that theory would detract

from defendant’s mitigation arguments); see also Vinyard v.

United States, 804 F.3d 1218, 1225 (7th Cir. 2018) (discussing

similarities between deference afforded trial and appellate

counsel’s strategic decisions; “winnowing down possible

claims to those an attorney believes are strongest is a classic

example of a strategic decision”).

In one Hobbs Act robbery case, other available theories for

defense or mitigation may seem solid enough that a lawyer

might reasonably decide, after a full investigation, not to pur-

24 No. 20-1623

sue a technical and counterintuitive guideline argument ask-

ing the court to break new legal ground. Such a strategy might

be particularly appropriate before a judge noted for minimiz-

ing the role of guideline calculations vis-à-vis the more gen-

eral considerations in 18 U.S.C. § 3553(a), where such a guide-

line argument might also seem unlikely to gain much traction.

Other judges may have well-known antipathy to the categor-

ical approach and regularly deviate from the Guidelines’ rec-

ommendations based on this policy disagreement. Effective

defense counsel might reasonably choose not to pursue this

guideline issue.

But in other cases, where other defenses and mitigation ar-

guments offer little traction, a failure to raise this available ar-

gument that would cut the guideline sentencing range by

more than half could be deemed ineffective. Moreover, a the-

ory that counsel sought to prioritize mitigation arguments

over guideline arcana cannot be considered in a vacuum. The

defense here proposed a sentence of 108 months, which was

50% higher than the high end of the proper guideline range.

And even discounting for the benefits of hindsight, counsel’s

argument that his 62-year-old client with a 45-year criminal

history, fresh off this robbery spree, would age out of crime at

age 68 never could have looked promising. Likewise, refusing

to do needed research because it “would have been extremely

difficult to do and time consuming” does not necessarily ex-

cuse deficient performance, Ramirez, 799 F.3d at 855, and the

research needed here does not seem to have been particularly

difficult or onerous in any event. See also Washington v. Smith,

219 F.3d 620, 631 (7th Cir. 2000) (performance was ineffective

where counsel failed to investigate because of “busy” sched-

ule).

No. 20-1623 25

B. Prejudice

The government has rightly conceded that the district

court’s denial of habeas relief without a hearing cannot be af-

firmed based solely on lack of prejudice. We briefly explain

why. To prove ineffective assistance of counsel, the defendant

must show “that there is a reasonable probability that, but for

counsel’s unprofessional errors, the result of the proceeding

would have been different.” Strickland, 466 U.S. at 694. In the

context of federal sentencing, “the Guidelines are not only the

starting point for most federal sentencing proceedings but

also the lodestar.” Molina-Martinez, 136 S. Ct. at 1346 (review-

ing caselaw and statistical reports). “In most cases a defend-

ant who has shown that the district court mistakenly deemed

applicable an incorrect, higher Guidelines range has demon-

strated a reasonable probability of a different outcome.” Id.

Here, the record shows that the district court and defense

counsel treated the erroneous range of 151 to 188 months as

the starting point. No evidence suggests that the district court

would have imposed a 140-month sentence even if the advi-

sory guideline had a high end of 71 months. See United

States v. Marks, 864 F.3d 575, 576 (7th Cir. 2017); see also Mo-

lina-Martinez, 136 S. Ct. at 1346 (listing factors that may rebut

presumption of reasonable probability of prejudice).

In this case, the district judge looked beyond the Guide-

lines, as she should have under § 3553(a). See also Gall v.

United States, 552 U.S. 38 (2007); Booker v. United States, 543

U.S. 220 (2005). “Sentencing convicted offenders is generally

recognized as the most difficult part of the job of a United

States District Judge,” United States v. Mzembe, 979 F.3d 1169,

1176–77 (7th Cir. 2020), and this case was especially challeng-

ing. Bridges was older than roughly 98% of all other federally

26 No. 20-1623

sentenced robbers in the year he was sentenced. U.S.S.C.,

Sourcebook of Federal Sentencing Statistics Table 7 (Fiscal Year

2018). He had a long and disturbing criminal history dating

back to his involvement in a home invasion and rape and rob-

bery as a teenager. Since those crimes, he had been convicted

of a bevy of other crimes, including criminal confinement and

several other robberies. Without downplaying his robbery

spree in this case, a judge might still recognize that his Hobbs

Act robberies did not display the violence and cruelty of pre-

vious crimes for which Bridges has already been punished.

His case also features significant mitigating circumstances, in-

cluding demonstrated progress in combatting his addictions

and learning disabilities. In other words, the statutory factors

that the sentencing court must consider in imposing a sen-

tence point strongly in different directions. See 18 U.S.C.

§ 3553(a). The district court thoughtfully engaged with these

facts in a nuanced way.

We have encouraged district courts facing seemingly arbi-

trary or difficult guideline issues to ask, “Why should anyone

care?” Marks, 864 F.3d at 582. The district court seemingly did

so here in attempting to consider where the 140-month sen-

tence would fall if the career offender guideline did not apply.

If the court had computed the counterfactual guideline range

properly, counsel’s possibly deficient performance might well

have withstood scrutiny. See Molina-Martinez, 136 S. Ct. at

1346. Unfortunately, however, the district court’s calculation

was erroneous, dropping the criminal history category from

VI to IV, but without also accounting for the large drop in the

offense level, from 29 to 21. The court thus mistakenly thought

that the 140-month sentence it imposed would have been

within the guideline range if the career offender enhancement

had not applied.

No. 20-1623 27

Cases such as this illustrate the importance of interrogat-

ing the Guidelines when unintuitive distinctions have a sig-

nificant impact on the advisory guideline range. The Guide-

lines are a comprehensive and detailed system that accounts

for the seriousness of criminal conduct and the defendant’s

criminal record. Such a system necessarily includes some ar-

bitrary rules and cutoffs. Marks, 864 F.3d at 582. Sentencing

courts are required to consider that advice, but they must also

consider the other factors listed in 18 U.S.C. § 3553(a) in craft-

ing a “sentence sufficient, but not greater than necessary, to

comply with” the statutorily enumerated purposes of sen-

tencing: punishment, deterrence, incapacitation, and rehabil-

itation. 5

District judges recognize that the career offender guide-

line frequently represents one such arbitrary cutoff. See

U.S.S.C., The Influence of the Guidelines on Federal Sentencing at

*55–56 (2020) (the career offender guideline has “been the sub-

ject of longstanding concern and has among the lowest

within-guideline rates each year”; the average sentence for

someone who has had the career offender guideline applied

is five and a half years shorter than the advisory guideline

minimum). The categorical approach grafts another arbitrary

cutoff onto this already problematic guideline.

That should not be a problem if sentencing courts follow

the process the district court took in this case: recognize that

5 Even when the Guidelines were mandatory, they invited departures

to account for arbitrary computations of criminal history. See

§§ 4B1.3; 5K2.0 (policy statement); see also, e.g., U.S.S.C., Sourcebook of Fed-

eral Sentencing Statistics Table 24 & Table 25 (Fiscal Year 2004) (reasons

given by sentencing courts for departures above and below the guideline

range, respectively).

28 No. 20-1623

the career offender guideline can significantly, and perhaps

arbitrarily, ratchet up an advisory range and attempt to craft

a sentence accounting for that discontinuity. See Gall, 552 U.S.

at 49–50. Where appropriate, such a move could be justified

by reference to either the § 3553(a) factors as they apply in the

particular case or a broader but reasonable policy disagree-

ment with the Guidelines. See United States v. Corner, 598 F.3d

411, 416 (7th Cir. 2010) (en banc), discussing, among other

cases, Spears v. United States, 555 U.S. 261 (2009) (per curiam),

Kimbrough v. United States, 552 U.S. 85 (2007), and Gall, 552 U.S

38.

We recognize that this decision further elevates the ab-

stract and artificial categorical approach over the known facts

of the case. But this method ensures that dramatic sentencing

enhancements are applied to only those defendants who

clearly fall within their intended scope. See United States v.

Sonnenberg, 628 F.3d 361, 367 (7th Cir. 2010). A district court

finding that a guideline definition is abstract, arbitrary, or ar-

duous should ask itself, with the § 3553(a) factors in mind,

why anyone should care how the answer comes out. “We are

ill-equipped to speculate” as to how the district court will an-

swer that question at a hypothetical future resentencing.

United States v. McGee, 985 F.3d 559, 564 (7th Cir. 2021).

The judgment in favor of respondent is REVERSED and

this case is REMANDED for further proceedings consistent

with this opinion.