United States v. Ramirez, 189 F. Supp. 3d 290

Background

Ramirez pled guilty in 2011 to federal drug offenses; the PSR designated him a career offender under U.S.S.G. §4B1.1 based on two prior convictions, producing a Guidelines range of 188–235 months; the district court sentenced him below that range to 156 months and later to 144 months on resentencing.
On direct appeal the First Circuit affirmed the career-offender designation as based solely on the Guidelines’ residual clause (U.S.S.G. §4B1.2(a)(2)), and Ramirez’s resentencing and subsequent appeals were unsuccessful; the Supreme Court denied certiorari in 2014.
After certiorari denial, the Supreme Court decided Johnson v. United States, invalidating the ACCA residual clause as void for vagueness; Ramirez then filed a §2255 motion arguing Johnson requires invalidation of the identical Guidelines residual clause and retroactive relief.
The government conceded Johnson invalidates the Guidelines residual clause but argued that applying Johnson to the Guidelines produces non-retroactive procedural changes; the district court conducted a Teague analysis to determine retroactivity.
The district court held the Guidelines’ residual clause is unconstitutionally vague under Johnson and that applying Johnson to invalidate the Guidelines clause announces a new substantive rule that must be applied retroactively on collateral review, entitling Ramirez to §2255 relief.

Issues

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether Johnson’s vagueness holding applies to the Guidelines’ residual clause	Johnson’s invalidation of the ACCA residual clause should extend to the identically worded Guidelines clause	Conceded the clause is invalid but emphasized differences in advisory Guidelines and procedural effects	Court: Johnson’s reasoning applies; the Guidelines’ residual clause is unconstitutionally vague
Whether applying Johnson to the Guidelines announces a "new rule" under Teague	The Johnson rule itself is sufficient and should be applied to the Guidelines	Argued two separate new rules would be required (vagueness + applicability to advisory Guidelines)	Court: Application to the Guidelines is a new rule (Johnson applied to Guidelines)
Whether that new rule is substantive (retroactive) or procedural (non‑retroactive)	Ramirez: Johnson is categorically retroactive; rule is substantive because it removes a class of defendants from career‑offender status	Government: As applied to advisory Guidelines the change is procedural — it only alters sentencing discretion, not statutory maximums	Court: The invalidation is substantive — career‑offender designation alters the class of punished persons and carries a substantial risk of a higher sentence, so it is retroactive
Remedy on collateral review under §2255	Vacate sentence and afford resentencing without the residual‑clause enhancement	Argued Johnson’s effect on Guidelines is non‑retroactive, so no collateral relief	Court: Granted §2255 relief and ordered vacation of sentence based on retroactive application

Key Cases Cited

Johnson v. United States, 576 U.S. 591 (2015) (ACCA residual clause void for vagueness)
Welch v. United States, 136 S. Ct. 1257 (2016) (Johnson’s retroactivity to ACCA holdings confirmed)
Teague v. Lane, 489 U.S. 288 (1989) (framework for retroactivity of new constitutional rules)
Booker v. United States, 543 U.S. 220 (2005) (Guidelines rendered advisory)
Schriro v. Summerlin, 542 U.S. 348 (2004) (distinction between substantive and procedural rules)
Peugh v. United States, 133 S. Ct. 2072 (2013) (Guidelines’ role in sentencing and Ex Post Facto considerations)
Montgomery v. Louisiana, 136 S. Ct. 718 (2016) (rules that carry substantial risk of unlawful punishment may be retroactive)