Bartolomeo v. United States, 316 F. Supp. 3d 539

Defendant pleaded guilty pursuant to a plea agreement in which the parties jointly recommended an upward departure and a 35‑year (420‑month) sentence; the agreement preserved the defendant’s right to seek future relief under 28 U.S.C. § 2255.
The plea and joint motion for upward departure relied on undisputed facts in the PSR about violent conduct (beating of Giorgio; killing of William Michaels) and expressly sought departure under USSG § 4A1.3.
At sentencing the court calculated offense level 32, found defendant a career offender (adjusting to offense level 37, CHC VI) yielding a guidelines range of 262–327 months, but granted the parties’ joint upward‑departure motion and imposed 35 years.
Post‑Johnson (Johnson II), the predicate Massachusetts assault and battery convictions used for career‑offender status no longer qualify as crimes of violence because they can be committed recklessly or intentionally.
Defendant filed a § 2255 petition arguing he no longer qualifies as a career offender and that, but for the enhancement, he would not have agreed to the 35‑year sentence (he would not have accepted such a large upward departure to avoid murder prosecution).
The court found defendant is not a career offender under the updated law, but denied relief because defendant failed to show a reasonable probability the sentence would have been different absent the designation.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Career‑offender predicates	Defendant: prior assault convictions no longer count post‑Johnson; thus not a career offender	Government: career‑offender finding was correct at sentencing	Court: Post‑Johnson, the Massachusetts offenses do not qualify; defendant is not a career offender
Cause to excuse procedural default	Defendant: Johnson II created novel, retroactive basis for collateral attack	Government: no dispute on novelty; argues career status irrelevant to ultimate sentence	Court: Johnson‑based claim satisfies cause (novelty) requirement
Prejudice — would sentence differ?	Defendant: he accepted plea believing career status made departure only ~8 years; without it he wouldn’t have accepted ~20‑year departure	Government: plea/joint motion and avoidance of murder charges, not career status, drove the deal and sentence	Court: No prejudice shown; record shows plea and upward departure were to avoid murder prosecution and would have been pursued regardless of career status
Relief under § 3582 (Amendment 782)	Defendant: seeks resentencing or reduction based on guideline changes	Government: sentence was not "based on" the Guidelines range; § 3582 inapplicable	Court: § 3582 relief unavailable where Guidelines range did not control the selection of the imposed sentence

Johnson v. United States, 135 S. Ct. 2551 (declaring ACCA residual clause void for vagueness)
Welch v. United States, 136 S. Ct. 1257 (Johnson applies retroactively to collateral challenges)
Beckles v. United States, 137 S. Ct. 886 (holding Johnson inapplicable to advisory Guidelines challenges in that context)
Booker v. United States, 543 U.S. 220 (rendering the federal Sentencing Guidelines advisory)
Strickler v. Greene, 527 U.S. 263 (prejudice standard — reasonable probability of different outcome)
Wilder v. United States, 806 F.3d 653 (§ 2255 burden and standards)
Moore v. United States, 871 F.3d 72 (First Circuit decisions applying Johnson to pre‑Booker career‑offender predicates)
United States v. Faust, 853 F.3d 39 (First Circuit on overbreadth of assault/BATTERY predicate under force clause)
United States v. Windley, 864 F.3d 36 (First Circuit on reckless assault not qualifying as violent felony)
Lattanzio v. United States, 232 F. Supp. 3d 220 (Johnson‑based claim satisfies novelty cause requirement)
Koons v. United States, 138 S. Ct. 1783 (limits § 3582 reductions to sentences that were based on the Guidelines range)