Bartolomeo v. United States, 960 F.3d 34

Background

In 1998 Bartolomeo pled guilty to federal drug distribution counts; his base offense level (BOL) from drug quantity was 32.
The PSR classified him as a career offender (two prior assault convictions), which would raise his BOL to 37 and place him in Criminal History Category VI.
The plea agreement and a joint motion for upward departure recommended an agreed sentence of 35 years, expressly tied to two uncharged violent incidents in 1995 (a severe beating and an intentional vehicle strike causing death).
At the combined plea/sentencing hearing the judge calculated the Guidelines (including the career-offender range) but stated she was "disposed to depart upward" and accepted the parties' recommendation of 35 years; the judgment listed mixed guideline figures.
In 2018 Bartolomeo filed a successive §2255 challenging his career-offender classification under intervening Supreme Court rulings (chiefly Johnson v. United States) and sought resentencing; the district court denied relief, finding no reasonable probability the sentence would have been different absent the career-offender designation.
The First Circuit affirmed, resting on the district court’s factual finding that the 35-year sentence flowed from the parties’ upward-departure recommendation and plea, not from reliance on the career-offender Guidelines range.

Issues

Issue	Plaintiff's Argument	Defendant's Argument	Held
Applicability of Johnson II to pre-Booker career-offender residual clause	Johnson II voids residual clause; pre-Booker career-offender status therefore invalid	Beckles and Booker limit Johnson II's reach; pre-Booker mandatory-Guidelines distinction may block application	Court did not decide the issue substantively here; treated the claim as having possible merit but resolved case on prejudice
Procedural default / cause to excuse failure to raise claim earlier	Johnson-based claim was novel; that novelty constitutes cause to excuse default	No cause; claim untimely or not available then	District court found cause satisfied; First Circuit did not disturb that finding
Actual prejudice (would sentence differ but for error)	But-for the career-offender range, Bartolomeo would not have accepted 35 years; substantial difference in Guideline caps shows prejudice	Sentence was the product of the joint upward-departure and plea bargain; judge imposed 35 years irrespective of underlying GSR	Court found no reasonable probability sentence would differ absent career-offender status and denied relief
Successive §2255 certification / timeliness / retroactivity	Johnson is new, retroactive rule that authorizes successive filing and tolls §2255 limitations	Johnson does not necessarily make pre-Booker career-offender claims timely or retroactive	First Circuit panel had authorized filing; appellate ruling avoided deciding broader retroactivity/timeliness issues by resolving prejudice question

Key Cases Cited

Johnson v. United States, 135 S. Ct. 2551 (2015) (ACCA residual clause held unconstitutionally vague)
Booker v. United States, 543 U.S. 220 (2005) (Guidelines are advisory, not mandatory)
Welch v. United States, 136 S. Ct. 1257 (2016) (Johnson II held retroactive on collateral review)
Beckles v. United States, 137 S. Ct. 886 (2017) (career-offender residual clause not void post-Booker for advisory Guidelines)
Moore v. United States, 871 F.3d 72 (1st Cir. 2017) (certified successive §2255 claim challenging pre-Booker career-offender residual clause)
Bousley v. United States, 523 U.S. 614 (1998) (cause-and-prejudice standard for collateral relief)
Strickler v. Greene, 527 U.S. 263 (1999) (reasonable-probability standard for prejudice)
Wilder v. United States, 806 F.3d 653 (1st Cir. 2015) (§2255 standards summarized)
Lassend v. United States, 898 F.3d 115 (1st Cir. 2018) (discussion of cause when claim was previously unavailable)
Brown v. United States, 139 S. Ct. 14 (2018) (denial of certiorari; Justice Sotomayor noted circuit split on pre-Booker career-offender claims)