# Jeffery Bridges v. United States

> Court of Appeals for the Seventh Circuit · March 17, 2021 · 991 F.3d 793

URL: https://www.frixlaw.com/law-library/cases/4668917

## Case

- **Court:** Court of Appeals for the Seventh Circuit
- **Decided:** March 17, 2021
- **Citations:** 991 F.3d 793
- **Precedential status:** Published
- **Opinion:** Opinion
- **Judges:** Hamilton
- **Nature of suit:** prisoner
- **Cited by:** 76 later opinions in the Frix Law Library

## Citator (automated)

- No negative treatment found by the automated citator. That is not the same as a confirmation that the case is good law; read the citing cases.
- Full citator and citing cases: https://www.frixlaw.com/law-library/cases/4668917

## How later opinions describe it (automated extraction)

- holding that denial of habeas relief could not be affirmed based on lack of prejudice where the court did not correctly calculate the non-career offender range or justify the sentence by reference to the § 3553(a) factors
- finding Hobbs Act robbery does not qualify as career offender predicate under the Guidelines because, unlike § 924(c), that definition does not include threats to property
- reversing the district court’s denial of postconviction relief under § 2255 because “the career offender guideline dramatically increased the advisory sentence, so that the issue deserved more attention than counsel had apparently given it”

## Opinion text

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.

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Source: Frix Law Library, https://www.frixlaw.com/law-library/cases/4668917. Public record. Not legal advice.