Jeffery Bridges v. United States, 991 F.3d 793

Background

Jeffrey Bridges (age 60s) committed four Hobbs Act robberies in March 2017, obtaining about $719; he was federally indicted and pleaded guilty to all counts.
His plea agreement stipulated application of the career-offender enhancement (U.S.S.G. §4B1.1), which raised his advisory range from about 57–71 months to 151–188 months; the district court imposed a 140‑month sentence (below the stipulated range).
Defense counsel did not challenge the Guidelines calculation at plea or sentencing; Bridges waived a direct appeal and later filed a §2255 petition alleging ineffective assistance of counsel for failing to contest the career-offender designation.
The district court denied relief without an evidentiary hearing, reasoning counsel was not required to anticipate unsettled circuit law.
The Seventh Circuit held (1) Hobbs Act robbery does not categorically qualify as a "crime of violence" under the amended U.S.S.G. §4B1.2 (2016 Amendment 798), and (2) Bridges is entitled to an evidentiary hearing on whether counsel was ineffective for failing to litigate that issue.

Issues

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether Hobbs Act robbery is a "crime of violence" under amended U.S.S.G. §4B1.2	Bridges: No — Hobbs Act reaches threats to property and thus is broader than the Guidelines' generic robbery/extortion definitions	Government: Yes or at least not clearly excluded; the categorical result is counterintuitive and unsettled	Held: Hobbs Act robbery is not a categorical fit for §4B1.2 as amended (agrees with other circuits)
Whether counsel’s failure to challenge the career-offender enhancement was constitutionally deficient	Bridges: Counsel should have researched Amendment 798 and out‑of‑circuit decisions (e.g., O'Connor) and raised the issue	Government: Counsel need not raise novel or counterintuitive arguments absent controlling in‑circuit precedent	Held: Possible deficiency; counsel may be required to press arguments foreshadowed by existing law — remand for evidentiary hearing
Whether lack of controlling circuit precedent forecloses an ineffective-assistance claim	Bridges: No — out‑of‑circuit precedent and the recent guideline amendment sufficiently foreshadowed the argument	Government: Yes — absent in‑circuit authority, failure to anticipate future holdings is reasonable	Held: Lack of in‑circuit precedent is not dispositive; the claim survives to hearing because the issue was sufficiently foreshadowed
Whether Bridges was prejudiced by counsel’s omission	Bridges: Yes — erroneous career-offender treatment dramatically increased the guideline range and likely affected the sentence	Government: District court discretion and §3553(a) factors could have produced the same sentence	Held: Prejudice cannot be resolved on the existing record; remand for hearing (district court miscalculated a counterfactual range)

Key Cases Cited

Johnson v. United States, 576 U.S. 591 (2015) (invalidated ACCA residual clause and prompted narrower guideline definition)
Descamps v. United States, 570 U.S. 254 (2013) (explaining the categorical approach to prior convictions)
Taylor v. United States, 495 U.S. 575 (1990) (foundational use of the categorical method)
Strickland v. Washington, 466 U.S. 668 (1984) (standard for ineffective assistance of counsel)
Beckles v. United States, 137 S. Ct. 886 (2017) (held advisory Guidelines’ residual clause not void-for-vagueness for sentencing)
Molina-Martinez v. United States, 136 S. Ct. 1338 (2016) (presumption of prejudice when incorrect Guidelines range used)
United States v. O'Connor, 874 F.3d 1147 (10th Cir. 2017) (Hobbs Act robbery not a Guidelines "crime of violence")
United States v. Camp, 903 F.3d 594 (6th Cir. 2018) (same conclusion re: Hobbs Act post‑Amendment 798)
United States v. Eason, 953 F.3d 1184 (11th Cir. 2020) (agreeing that Hobbs Act robbery falls outside amended §4B1.2)