Bartolomeo v. United States

United States Court of Appeals
For the First Circuit

No. 18-1621

JOHN R. BARTOLOMEO,

Petitioner, Appellant,

v.

UNITED STATES OF AMERICA,

Respondent, Appellee.

APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Rya W. Zobel, U.S. District Judge]

Before

Howard, Chief Judge, and
Lynch and Lipez, Circuit Judges.

Bernard Grossberg for petitioner-appellant.

Jennifer Hay Zacks, Assistant United States Attorney, with
whom Andrew E. Lelling, United States Attorney, was on brief, for
respondent-appellee.

May 29, 2020
 LIPEZ, Circuit Judge. In May 1998, a district court

sentenced petitioner John Bartolomeo to thirty-five years'

imprisonment for drug dealing pursuant to a plea agreement

recommending that specific prison term. The above-Guidelines

sentence was intended to reflect Bartolomeo's role in two uncharged

violent crimes: his severe beating of one member of a rival

motorcycle club and his intentional, fatal striking of a second

member with his car. Nearly twenty years later, in January 2018,

Bartolomeo filed a successive federal habeas petition pursuant to

28 U.S.C. § 2255 based on intervening Supreme Court caselaw holding

the residual clause of the Armed Career Criminal Act ("ACCA")

unconstitutional. See Johnson v. United States (Johnson II), 135

S. Ct. 2551 (2015); United States v. Booker, 543 U.S. 220 (2005).

Claiming that his status as a "career offender" under the

Sentencing Guidelines impacted his sentence and that the new

precedent on the ACCA also invalidated that Guidelines

classification, Bartolomeo requested resentencing to a lesser term

of imprisonment. The district court ("the habeas court") denied

Bartolomeo's habeas petition and granted a certificate of

appealability. See 28 U.S.C. § 2253(c)(2). Because we agree with

the habeas court that the sentencing judge did not rely on

Bartolomeo's career-offender designation in setting his term of

imprisonment, we affirm the denial of Bartolomeo's petition.

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 I.

We draw the following factual summary primarily from

Bartolomeo's plea agreement, the transcript of his combined plea

and sentencing proceeding, and uncontested portions of his

Presentence Investigation Report ("PSR").

A. Indictment and PSR

In a seventeen-count superseding indictment filed in

October 1996, Bartolomeo, a member of the Hells Angels motorcycle

club, was charged with conspiring to distribute cocaine and

methamphetamine, and with possessing those drugs with the intent

to distribute them. Based on the quantity of drugs for which he

was deemed responsible, Bartolomeo's PSR calculated his base

offense level ("BOL") as 32. However, the PSR also stated that

his prior convictions qualified Bartolomeo as a career offender

under the Sentencing Guidelines, see U.S.S.G. § 4B1.1,1 which

1
The applicable version of the Guidelines provided that "[a]
defendant is a career offender if
(1) the defendant was at least eighteen years
old at the time the defendant committed the
instant offense of conviction; (2) the instant
offense of conviction is a felony that is
either a crime of violence or a controlled
substance offense; and (3) the defendant has
at least two prior felony convictions of
either a crime of violence or a controlled
substance offense.
U.S.S.G. § 4B1.1 (1997). A crime of violence under the Guidelines
was defined as a federal or state law offense specifically named,
including burglary of a dwelling and arson, as well as any crime
that "otherwise involves conduct that presents a serious potential

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increased his offense level to 37 and produced a Criminal History

Category ("CHC") of VI.2

The PSR contained an undisputed description of

Bartolomeo's involvement in two violent crimes against members of

a rival motorcycle club. The first was described, in pertinent

part, as follows:

[O]n July 1, 1995, Bartolomeo and others
chased Girard Giorgio on Route 3. Giorgio, a
member of the Devil's Disciples Motorcycle
Club, was riding his motorcycle with another
member of the Devil's Disciples at the time.
When Bartolomeo and others caught up with
Giorgio, they beat him badly and stripped him
of his Devil's Disciples "colors."

About two weeks after this incident, Bartolomeo bragged

to an undercover officer posing as a drug customer that "two or

three weeks" earlier he had "kicked in the teeth" of a Devil's

Disciples member and "boasted that this individual was still in

critical condition and that [Bartolomeo] would have stabbed this

individual in the heart if there had been fewer people around."

risk of physical injury to another." Id. § 4B1.2(a)(2) (1997).
The portion of the definition beginning with "otherwise" is known
as "the residual clause."
2 As the habeas court observed, "[t]he predicate convictions
for the career offender classification are not entirely clear."
Bartolomeo v. United States, 316 F. Supp. 3d 539, 542 (D. Mass.
2018). However, the parties have proceeded on the assumption that
the triggering predicates are Bartolomeo's 1993 conviction for
assault and battery and his 1995 conviction for assault and battery
on a police officer. See id.

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The second episode occurred about two weeks after the conversation

with the undercover officer recounted above:

On Saturday, July 29, 1995, Bartolomeo
accelerated his automobile at the intersection
of Route 18 and Park Avenue in Weymouth and
struck William Michaels. Michaels, a member
of the Devil's Disciples, was riding his
motorcycle at the time. Michaels later died
as a result of the collision.

B. Plea Agreement

In May 1998, Bartolomeo entered into a plea agreement

with federal and state prosecutors in which he agreed to plead

guilty to twelve drug distribution counts and two criminal

forfeiture counts. The agreement stated that Bartolomeo's BOL was

32 -- i.e., the level calculated by the PSR based on the drug

quantity for which he was held responsible. The agreement noted

that Bartolomeo was subject to a three-level upward adjustment for

his role in the offense and an offsetting three-level decrease in

his BOL for acceptance of responsibility, thus producing a total

offense level ("TOL") of 32. The agreement did not reference the

PSR's career-offender designation, and it stated that the parties

had not reached an agreement on the appropriate CHC.

Under the heading "Sentence Recommendation," the

agreement reported that "[t]he parties will make a joint

recommendation to the Court at the Defendant's sentencing hearing

that the Court depart upwards from the guideline range otherwise

applicable to the Defendant and impose a sentence of 35 years'

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imprisonment." The agreement expressly linked this upward

departure to Bartolomeo's involvement in the two violent incidents

described above. Under the heading "Upward Departure," the

agreement provided:

As set forth in the joint motion for an upward
departure attached to this agreement, the
parties agree that the undisputed facts
contained in the Defendant's Presentence
Report concerning the Defendant's
participation in the assault and battery of
Girard Giorgio on July 1, 1995 and the
Defendant's responsibility for the death of
William Michaels on July 29, 1995 warrant an
upward departure pursuant to § 4A1.3(e) of the
Sentencing Guidelines.3

Pursuant to the agreement, if the sentencing court

accepted the recommended thirty-five-year term, the United States

Attorney would not charge Bartolomeo with any federal crime based

on the two July 1995 incidents, and the pertinent Massachusetts

district attorney would not charge him with violating any state

3 The applicable version of Guidelines section 4A1.3, which
is designated as a "Policy Statement," provided that an upward
departure may be warranted "[i]f reliable information indicates
that the criminal history category does not adequately reflect the
seriousness of the defendant's past criminal conduct." The section
explains that "[s]uch information may include . . . (e) prior
similar adult criminal conduct not resulting in a criminal
conviction." U.S.S.G. § 4A1.3 (1997). The referenced departure
motion -- submitted jointly by the government and Bartolomeo --
stated that Bartolomeo acknowledged his participation in the two
violent incidents and that this "uncharged conduct
. . . constitutes a basis for an upward departure" under the
Guidelines. The motion further noted the parties' agreement that
the undisputed facts warranted an upward departure beyond the range
provided by CHC VI, the highest category.

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law based on the motor vehicle striking incident.4 As part of the

agreement, Bartolomeo waived his right to appeal his conviction

and sentence, and waived collateral challenges under 28 U.S.C.

§ 2255 except for those based on "any future decision, ruling,

change in law or change in the Sentencing Guidelines [that] may

result in a reduction in the total time of the Defendant's

incarceration."

C. Change of Plea and Sentencing

The district court accepted Bartolomeo's guilty plea and

sentenced him in a combined proceeding held in May 1998. We

describe each portion of that proceeding in turn.

1. Change of Plea

Early in its change-of-plea colloquy with Bartolomeo,

the sentencing court reviewed the charges against him and confirmed

that Bartolomeo understood them. The court emphasized the jury-

trial rights that Bartolomeo would be giving up by pleading guilty,

and it noted the statutory minimum and maximum sentences applicable

to the crimes charged. The court asked Bartolomeo if he understood

the plea agreement, and Bartolomeo answered affirmatively. The

court also generally described the Sentencing Guidelines,

confirmed that Bartolomeo had discussed them with his attorney,

4
The parties do not explain why the state prosecutor's
agreement applied only to the later incident, but the discrepancy
is not material to our analysis.

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and noted that "unless there's something very special, very evil,

really, about you, and they say there is in this case, I can't go

above the top of that range and then I can't go below the bottom

of the range."

The court then questioned the government's attorney on

the Guidelines calculation, as follows:

COURT: And I'm going to ask [Assistant United
States Attorney ("AUSA")] Hobart, unless it's
done here in the plea agreement, and it does
not appear to be done, despite the joint
recommendation for an upward departure, before
we go any further he needs to know where the
sentencing guidelines put him. Would you
calculate them in the aggregate for me very
briefly, bottom line, giving him credit for
acceptance of responsibility.
AUSA: Yes, your Honor. Under the plea
agreement I think, I believe the total offense
level would be 32, going up three points for
role in the offense and down three points for
acceptance of responsibility. Without taking
into account any career offender provisions,
the maximum amount, maximum range would be 262
months in a criminal history category of VI.
COURT: And your position is that he's at a
criminal history category VI?
AUSA: I believe that the probation department
found that to be so, your Honor.
COURT: Okay. So he's . . . at level 32,
correct?
AUSA: Correct, your Honor.
COURT: Criminal history category VI?5
AUSA: Correct.
COURT: So that gives a minimum --
AUSA: That's just upon the drug quantity. And
then if the probation department's

5 Contrary to this agreement on CHC VI, that category applied
only to the career-offender classification. In the sentencing
portion of the proceeding, the district court noted that
Bartolomeo's CHC was III without that enhancement. See infra.

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 determination were accepted, he was found to
be a career offender, his base offense level
would be set at 37, three levels reduction for
acceptance of responsibility for 34, which
would produce a range of 262 to 327.
COURT: All right, but . . . [d]on't you have
to give notice that you're prosecuting him as
a career offender? You don't?
AUSA: No, you don't.
COURT: All right. So now if he pleads guilty
to these, what is your position as to whether
he's a career offender?
AUSA: Neither myself nor Mr. Natola [defense
counsel] filed any objections to that portion
of the presentence report.
COURT: Which calculates that he is.
AUSA: Yes.
COURT: All right. So really we're talking 262
to 327 months under the sentencing guidelines.
AUSA: Right. And not to speak for Mr. Natola,
but in light of the agreement, I filed a joint
motion for upward departure, there wasn't any
reason for Mr. Natola to object to that
determination.
COURT: And I fully understand that. It's just
so important to me that Mr. Bartolomeo
understands each step in this procedure.
So, 262 months under the sentencing
guidelines, if I don't do anything, it's 21
years and some months, 327 months, the range
is 21 years and some months to 25 years and
some months, based upon what I'm told.6
Is that how the sentencing guidelines
have been explained to you?
BARTOLOMEO: Yes, sir.

The court then focused specifically on the joint motion

for upward departure, observing that the court could depart upward

even without a motion but advising Bartolomeo that "when they both

tell me that I ought to depart upward, I have to tell you it's

6 In fact, 262 months is nearly twenty-two years, and 327
months is about twenty-seven years.

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much more likely that I will." Asked if he understood that, "as

a functional matter now, . . . you're really looking at 35 years

in prison if you plead guilty," Bartolomeo responded, "Yes, I do,

sir."

The court then pointed out that the upward departure was

based on the "incident involving a William Michaels," obtained

assurance from the government that both federal and state

authorities had agreed not to prosecute Bartolomeo for that conduct

in exchange for his guilty plea on the drug charges, and elicited

Bartolomeo's admission that the depiction of the drug offenses

presented in the PSR was accurate. The court then accepted

Bartolomeo's guilty plea to the fourteen drug and criminal

forfeiture counts, finding that the plea was "knowingly,

intelligently and voluntarily" made.

2. The Sentencing

The sentencing portion of the proceeding began with the

court's description of its intended approach:

COURT: I think in framing your arguments I
should say that, one, though I'm going to do
the sentencing guideline calculations, I am
disposed to depart upward on the grounds of
the joint motion; and two, implicit in my
acceptance of the plea after a pre-plea
presentence report, I am disposed to accept
the joint recommendation and sentence no more
nor less severely.
Now, with that in mind, I'm going to do
the calculations required by the sentencing
guidelines. If anyone would differ with them,

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 please call that to my attention and I will,
I will entertain it right at that time.
The base offense level in this case is
32. I am adjusting upward by three levels for
Mr. Bartolomeo's role in the offense finding
that he is a manager or supervisor of this,
these drug transactions. I am going to adjust
downward three levels for his acceptance of
responsibility, . . . taking us back to a
total offense level of 32. . . . I do find
that he is a career offender and that applying
the career offender guidelines his
corresponding offense level is 37. As he is
a career offender, his criminal history
category, which otherwise would be III, is
calculated at VI, which gives us a sentencing
range of not less than --
AUSA: He would also receive a three[-]level
decrease, your Honor, for acceptance. His
total offense level would be 34, not 37.
COURT: Is that right? The probation officer?
That's where you --
PROBATION: Yes, your Honor.
COURT: -- calculate it in?
PROBATION: Yes.
COURT: . . .
That gives us a sentencing range as we
discussed with Mr. Bartolomeo of not less than
262 nor more than 327 months, and tentatively
that's how I calculate the guidelines.
You accept that, Mr. Hobart?
AUSA: Yes, your Honor.
COURT: You accept that, Mr. Natola?
NATOLA: Yes, I do, your Honor.

The court then heard from both counsel, beginning with

the government. AUSA Hobart explained that "[t]he factual basis

for the government's upward departure involves the death of William

Michaels on July 29, 1995," and he went on to detail the

circumstances of that incident, including Bartolomeo's subsequent

flight to New York and his time spent in hiding there. Defense

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counsel added only a brief comment, expressing agreement with the

Guidelines calculation "and also with the factual basis for the

motion for upward departure."

Before allowing Bartolomeo to speak, the court noted

that "this William Michaels thing . . . would be the basis of my

upward departing," and it therefore asked Bartolomeo if it were

"true[] that you intentionally struck William Michaels on July 29,

1995, using your vehicle while he was riding a motorcycle?"

Bartolomeo answered, "Yes, it is." The court reiterated the state

of mind question, asking, "And you did that intentionally, ran him

down intentionally?" Bartolomeo responded, "Yes, I did."

Accepting the court's invitation to speak at that point, Bartolomeo

spoke at some length about being "a man with fierce loyalty,"

learned from his parents and siblings, "and my brothers that are

here from the Hells Angels." Among his other statements,

Bartolomeo asserted that, "if you told me today that I could go

home to my family if I would denounce being a member of the Hells

Angels, I wouldn't do it. I'm a Hells Angel, in my heart and my

bones." Bartolomeo indicated disapproval for criminal defendants

who "take the easy way out" and cooperate with the government in

exchange for a reduced sentence, and, accusing the undercover law

enforcement agent of "betray[ing]" him, asserted that he "could

never do that to somebody."

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 Immediately following Bartolomeo's remarks, the court

sentenced him to thirty-five years' imprisonment on one count,

"and either 35 years or the maximum sentence on each of the

remaining counts," with all sentences to run concurrently. The

court directly addressed Bartolomeo to explain the sentence:

You haven't got the first idea about loyalty.
Don't sully the names of those who have served
the nation by your conduct, your drug dealing,
your spreading of poison throughout the
community. You disgrace those who know what
the meaning of loyalty is. Loyalty has to do
with things greater than yourself. You have
done nothing but serve your own needs as you
perceived them at the time. You have shown no
value for human life or health or care for
anyone. You say that's the road you've
chosen. So be it.

In its Statement of Reasons issued with the judgment, the

sentencing court listed the TOL as 32, the level applicable without

career-offender status, but it listed the greater imprisonment

range (262 to 327 months) and CHC (VI) that applied to the career-

offender guideline.

II.

Insisting that his thirty-five-year sentence, and his

willingness to accept it, depended on his status as a career

offender, Bartolomeo asserts in his habeas petition that he is

entitled to resentencing to a lesser term of imprisonment because,

under current law, he was wrongly classified as a career offender.

Bartolomeo argues that he may bring this claim two decades after

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his sentencing because a series of recent Supreme Court cases

effected a "change in law" that "may result in a reduction in the

total time of [his] incarceration" -- precisely the circumstance

excepted from the appellate waiver contained in his plea agreement.

See supra Section I.B (quoting the plea agreement). He further

maintains that he satisfies the requirements for habeas relief

under 28 U.S.C. § 2255.

We begin our analysis by reviewing the Supreme Court

sentencing precedent on which Bartolomeo relies and the components

of a challenge under § 2255. We then briefly recount the habeas

court's reasoning in rejecting Bartolomeo's habeas petition before

turning to our own assessment of his claim.

A. Predicate Crimes post-Johnson II7

Both the ACCA, 18 U.S.C. § 924(e), and the career

offender provision of the Sentencing Guidelines, U.S.S.G. § 4B1,

provide for enhanced punishment for certain repeat offenders.

Under the ACCA, "a defendant convicted of being a felon in

possession of a firearm faces more severe punishment if he has

three or more previous convictions for a 'violent felony.'"

Johnson II, 135 S. Ct. at 2555. Before the Supreme Court's

decision in Johnson II, the statute had defined a "violent felony"

7
Johnson I addressed the "force" clause of the ACCA, which
is not implicated in this case. See Johnson v. United States, 559
U.S. 133 (2010).

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to include any felony, in addition to certain specified violent

crimes, that "otherwise involves conduct that presents a serious

potential risk of physical injury to another." 18 U.S.C.

§ 924(e)(2)(B) (2012). The Court struck down this portion of the

definition -- the so-called residual clause -- as

unconstitutionally vague, 135 S. Ct. at 2557, and it subsequently

held that Johnson II's holding applied retroactively to collateral

challenges, see Welch v. United States, 136 S. Ct. 1257, 1268

(2016).

The Supreme Court later considered whether "the

identically worded residual clause" in the career-offender

provision of the Guidelines -- defining a "crime of violence"8 --

suffers from the same constitutional defect. See Beckles v. United

States, 137 S. Ct. 886, 890 (2017). The Court held that it does

not -- at least since the Court ruled that the Guidelines must be

treated as advisory rather than mandatory. Id. at 894-95; see

Booker, 543 U.S. at 245 (deeming the Guidelines advisory). In a

concurrence, Justice Sotomayor noted that the Court had left open

whether defendants who were sentenced under the pre-Booker

8 We have observed that the equivalence in language between
the ACCA definition of a "violent felony" and the Guidelines
definition of a "crime of violence" "makes decisions 'interpreting
one phrase frequently . . . persuasive in interpreting the
other.'" United States v. Ramírez, 708 F.3d 295, 301 n.4 (1st
Cir. 2013) (quoting United States v. Winter, 22 F.3d 15, 18 n.3
(1st Cir. 1994)).

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mandatory Guidelines regime, like Bartolomeo, "may mount vagueness

attacks on their sentences." Beckles, 137 S. Ct. at 903 n.4

(Sotomayor, J., concurring in the judgment).

The argument that Bartolomeo presents in his habeas

petition -- that he was improperly classified as a career offender

-- is thus anchored in Johnson II, Welch and Beckles,9 but the

Supreme Court has not yet answered the specific question on which

his petition turns: whether the reasoning of Johnson II applies to

career-offender determinations made prior to Booker, when the

Guidelines were mandatory. Justice Sotomayor, joined by Justice

Ginsburg, dissented from the denial of certiorari in a 2018 case

that could have resolved the circuit split on that question. See

Brown v. United States, 139 S. Ct. 14, 15-16 (2018) (Sotomayor,

J.) (dissenting from denial of certiorari and describing the

differing circuit decisions)10; id. at 16 (stating that "this case

9 The parties in this case agree that, if the residual clause
in the career-offender provision was unconstitutionally vague at
the time Bartolomeo was sentenced, he could no longer be classified
as a career offender because the two predicate convictions presumed
to underlie that classification do not otherwise qualify as
"crime[s] of violence."
10Our court also has not decided whether a habeas petitioner
may rely on the reasoning of Johnson II to challenge the identical
language in the mandatory Guidelines. In listing the cases that
comprise the circuit split, Justice Sotomayor recognized that the
First Circuit had not yet taken a position on the issue, but she
noted her view that we had "strongly hint[ed] yes" in Moore v.
United States, 871 F.3d 72, 80-83 (1st Cir. 2017). See Brown, 139
S. Ct. at 15-16. We briefly discuss Moore in Section II.B.

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presents an important question of federal law that has divided the

courts of appeals and in theory could determine the liberty of

over 1,000 people").11

B. Federal Habeas Review

To obtain the post-conviction relief that he seeks

pursuant to § 2255 -- resentencing to a lower term of imprisonment

-- Bartolomeo must show that "his sentence 'was imposed in

violation of the Constitution or laws of the United States' or 'is

otherwise subject to collateral attack.'" Wilder v. United States,

806 F.3d 653, 658 (1st Cir. 2015) (quoting 28 U.S.C. § 2255(a)).

Bartolomeo says he has accomplished that showing based on the

unconstitutional vagueness of the Guidelines' career-offender

provision. However, because he did not assert such a claim at his

sentencing or on direct appeal -- a procedural default --

Bartolomeo would not be entitled to resentencing even if we agreed

with him unless he also can show "'cause' that excuses the

procedural default and 'actual prejudice' resulting from the

alleged error." Id. (quoting Bousley v. United States, 523 U.S.

614, 622 (1998)). Cause exists if the "claim was 'so novel that

its legal basis [wa]s not reasonably available to counsel' at the

time of the default." Lassend v. United States, 898 F.3d 115, 122

11
As Justice Sotomayor noted, "after Johnson [II], the
Sentencing Commission deleted the residual clause from the
Guidelines." Brown, 139 S. Ct. at 15 (citing U.S.S.G.
§ 4B1.2(a)(2) (2016)).

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(1st Cir. 2018) (alteration in original) (quoting Reed v. Ross,

468 U.S. 1, 16 (1984)). For actual prejudice, Bartolomeo "must

show that 'there is a reasonable probability' that" he would have

received a different sentence "but for the alleged error." Wilder,

806 F.3d at 658 (quoting Strickler v. Greene, 527 U.S. 263, 289

(1999)).

Before addressing the habeas court's holdings on cause

and prejudice, we pause to describe an additional barrier that

Bartolomeo needed to scale in this case. Because he previously

had filed unsuccessful motions under § 2255 attacking his

sentence, Bartolomeo could not file this successive motion without

certification from our court that he is relying on "a new rule of

constitutional law, made retroactive to cases on collateral review

by the Supreme Court, that was previously unavailable." 28 U.S.C.

§ 2255(h)(2).12

In late 2017, a First Circuit panel authorized

Bartolomeo's challenge to his career-offender designation, see

Bartolomeo v. United States, No. 16-1317 (1st Cir. Nov. 17, 2017)

(judgment granting leave to file successive § 2255 motion), based

on two then-recent First Circuit decisions certifying habeas

petitions raising career-offender claims premised on Johnson II.

12Another subsection of § 2255(h) pertains to newly
discovered evidence and is inapplicable here. See 28 U.S.C.
§ 2255(h)(1).

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One of those cases was Moore, the decision noted by Justice

Sotomayor in her Brown dissent. See supra Section II.A. The

other, Hardy v. United States, 871 F.3d 85 (1st Cir. 2017), was

issued at the same time as Moore, and it summarily certified the

Johnson II issue raised there based on the reasoning set forth in

Moore. See Hardy, 871 F.3d at 86 (certifying a successive § 2255

motion "insofar as it argues that Johnson II invalidates the

residual clause of the pre-Booker career offender guideline").

Notably, however, we did not decide in Moore and Hardy

that the Johnson II claims were meritorious; rather, consistent

with applicable law, we determined only that the defendants had

met their burden to show the "possible merit" of the claims.

Moore, 871 F.3d at 78 (quoting Rodriguez v. Superintendent, Bay

State Corr. Ctr., 139 F.3d 270, 273 (1st Cir. 1998), abrogated in

part by Bousley v. United States, 523 U.S. 614 (1998)).13

13 The "possible merit" of the claims accomplished the prima
facie showing that is among several statutory requirements aimed
at ensuring accelerated review of certification requests. See
Moore, 871 F.3d at 77 (describing the appellate court's
consideration of such requests as "fast, unreviewable, and
limited"). Under § 2255(h), "[a] second or successive motion must
be certified as provided in section 2244." The latter provision,
inter alia, imposes a thirty-day deadline to rule on certification,
28 U.S.C. § 2244(b)(3)(D); states that a grant or denial is neither
appealable nor subject to rehearing, id. § 2244(b)(3)(E); and
permits the petition upon a prima facie showing that the claim
relies on "a new rule of constitutional law," previously
unavailable, that the Supreme Court has "made retroactive to cases
on collateral review," id. § 2244(b)(3)(C),(2)(A).

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 In brief, the Moore panel found the requisite merit in

the petitioner's argument that the pre-Booker Guidelines were

sufficiently binding on sentencing judges that the career-offender

residual clause under that regime was equivalent to the ACCA's

residual clause and, hence, suffered from the same constitutional

flaw. See 871 F.3d at 81-82; see also id. at 82 ("[I]f one takes

seriously, as we must, the Court's description of the pre-Booker

guidelines as 'mandatory,' one might describe the residual clause

of the pre-Booker guidelines as simply the ACCA's residual clause

with a broader reach, in that it fixed increased minimum and

maximum sentences for a broader range of underlying crimes.").

Ultimately, however, the panel left it to the district court to

decide "whether the pre-Booker guidelines fixed Moore's sentencing

range in the relevant sense that the ACCA fixed sentences." Id.

at 84.14 The district court did subsequently allow Moore's petition

to vacate and correct his sentence. See United States v. Moore,

No. 1:00-10247-WGY-1, 2018 WL 5982017, at *3 (D. Mass. Nov. 14,

2018).

Our court's certification of Bartolomeo's similar

Johnson II claim allowed him to file his § 2255 motion in district

14
The Moore panel noted the possibility that Johnson II might
not apply categorically to the pre-Booker Guidelines: "If there is
. . . a difference in how mandatory the pre-Booker guidelines were
from case to case, then it may well be necessary to invalidate the
residual clause for those defendants for whom the guidelines fixed
sentences but not for others." 871 F.3d at 84.

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court, resulting in the decision -- described below -- that is now

on appeal.

C. The Decision on Habeas Review

In discussing Bartolomeo's claim, the habeas court began

by addressing the merits of the issue we did not definitively

resolve in Moore: whether the pre-Booker residual clause had the

same constitutional flaw as the ACCA's identical clause. The court

accepted the view adopted by several other judges within the

District of Massachusetts that "petitioners sentenced under the

residual clause of the mandatory, pre-Booker career offender

guideline may be entitled to resentencing under Johnson II."

Bartolomeo v. United States, 316 F. Supp. 3d 539, 546 (D. Mass.

2018); see also, e.g., Boria v. United States, 427 F. Supp. 3d

143, 149 (D. Mass. 2019); United States v. Roy, 282 F. Supp. 3d

421, 425-28 (D. Mass. 2017); Reid v. United States, 252 F. Supp.

3d 63, 66-68 (D. Mass. 2017). Therefore, because Bartolomeo's

predicate crimes no longer qualified for career-offender status,

the court went on to consider whether Bartolomeo satisfied the

requirements for habeas relief.

Relying on earlier precedent in the District, the court

readily concluded that Bartolomeo had shown "cause" for his

procedural default in failing to previously raise the career-

offender claim. See 316 F. Supp. 3d at 546. The court quoted

multiple decisions opining that the cause requirement was plainly

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met, including the observation in United States v. Lattanzio that,

"[i]n 1995, when Defendant here was sentenced, any argument based

on the rationales approved twenty years later in the Johnson cases

would have been not only novel, but practically unimaginable."

232 F. Supp. 3d 220, 223 (D. Mass. 2017); see also, e.g., United

States v. Webb, 217 F. Supp. 3d 381, 390 (D. Mass. 2016) (referring

to "the monumental shift that Johnson II created in sentencing").

However, the court found that Bartolomeo's circumstances

differed from "the ordinary Johnson [II] case, [in which] cause

and prejudice are the twinned results of sentencing for offenses

that no longer qualify as career offender predicates." Bartolomeo,

316 F. Supp. 3d at 546. Based on its review of the record, the

court concluded that, although Bartolomeo's career-offender status

was factored into the sentencing judge's calculation of the

applicable Guidelines range, the judge did not rely on the GSR

calculation in sentencing Bartolomeo. See id. at 546-47. Rather,

it was the "joint motion for upward departure that ultimately

determined the sentence." Id. at 547. The court further found

that the plea agreement indicated "petitioner's assent [to the

thirty-five-year term] irrespective of any career offender

designation." Id.

Hence, the court held, because Bartolomeo failed to show

that his sentence was affected by his career-offender status, he

has "not shown a reasonable probability that, but for his career

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offender designation, he would have received a different

sentence." Id. The court therefore denied the petition for habeas

relief for failure to show actual prejudice. Id. at 548.

III.

On appeal, Bartolomeo argues that the habeas court

misread the record in disregarding the impact of his career-

offender status on his sentencing. Bartolomeo claims, inter alia,

that he would not have agreed to a thirty-five-year term of

imprisonment if the starting point for departure had been a GSR

capped at about sixteen years (151-188 months) rather than the

roughly twenty-seven-year cap (262-327 months) resulting from the

career-offender GSR. In effect, he claims that he bargained for,

and agreed to, an upward departure of about eight years, not nearly

twenty years.

For its part, the government not only defends the habeas

court's assessment of the record on prejudice, but it also urges

us to conclude that Bartolomeo failed to show cause for his

procedural default. It further argues that we should conclude

that the pre-Booker Guidelines were "insufficiently 'mandatory'"

to fall within Johnson II's holding, both in general and as applied

to Bartolomeo's specific circumstances. Finally, the government

contends that Bartolomeo's petition is untimely because the

Supreme Court has not yet recognized "the right asserted," 28

U.S.C. § 2255(f)(3) -- i.e., he is not entitled to an extension of

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the one-year limitations period for habeas petitions because

Johnson II did not establish the unconstitutionality of the pre-

Booker career-offender guideline. See 28 U.S.C. § 2255(f)(3)

(stating that the "1-year period of limitation . . . shall run

from the latest of-- . . . the date on which the right asserted

was initially recognized by the Supreme Court, if that right has

been newly recognized by the Supreme Court and made retroactively

applicable to cases on collateral review").

In addressing the competing arguments, we review the

district court's findings of fact for clear error and its legal

rulings de novo. Lassend, 898 F.3d at 122.

A. The Government's Alternative Bases for Disposition

We begin by putting to one side the government's proposed

alternative rationales for upholding the denial of Bartolomeo's

habeas petition -- that is, the reasons other than a lack of actual

prejudice. Those rationales all require novel legal rulings that

are unnecessary if we agree with the habeas court's view that the

record reveals no reasonable probability that Bartolomeo would

have received a different sentence absent his classification as a

career offender. Although the First Circuit panel that certified

Bartolomeo's claim concluded that he made a prima facie showing of

merit on the applicability of Johnson II to the pre-Booker

Guidelines residual clause, any substantive holding by us beyond

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that threshold would be dicta if Bartolomeo cannot show actual

prejudice. We therefore turn to the prejudice question.

B. Assessing Prejudice

As Bartolomeo acknowledges, the prejudice inquiry --

whether he has shown "a reasonable probability," Strickler v.

Greene, 527 U.S. 263, 289 (1999), that he would have received a

different sentence "but for the alleged error," Wilder, 806 F.3d

at 658 -- is fact-dominated. Our review of the habeas court's

finding is therefore for clear error.

Bartolomeo argues that the roughly twelve-year

difference between the top of the career-offender guideline range

-- 327 months -- and the top of the otherwise applicable range --

188 months -- is the "actual prejudice" he suffered. In other

words, with the same amount of departure -- roughly eight years

from the top of the range -- he claims his sentence without career-

offender status should be about twenty-three years instead of

thirty-five. Bartolomeo appears to rely on two primary theories

in arguing that his career-offender status played a role in the

sentencing judge's imposition of the thirty-five-year term.

First, he emphasizes the sentencing court's repeated reference to

the Guidelines throughout the plea and sentencing proceeding as

evidence that his sentence was anchored in the Guidelines,

including the career-offender enhancement. Second, Bartolomeo

maintains that his career-offender status was built into the plea

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agreement and joint motion for upward departure and, hence,

adoption of the parties' recommendation necessarily incorporated

that status. We begin with the latter contention.

1. The Parties' Recommendation

The record amply supports the habeas court's finding

that Bartolomeo's career-offender status played no role in the

parties' selection of the thirty-five-year term specified in both

the plea agreement and the joint motion. The motion simply

proposed the upward departure to thirty-five years "from the

guideline range otherwise applicable to Bartolomeo." The plea

agreement likewise lacks any indication that Bartolomeo's

designation as a career offender influenced the sentencing

recommendation. Even the initial version of the agreement -- which

predated the PSR's report of Bartolomeo's career-offender status

-- called for the same thirty-five-year sentence. See Bartolomeo,

316 F. Supp. 3d at 547. Moreover, the signed plea agreement stated

that the parties had not agreed on a CHC; if the parties had

presumed career-offender status, the CHC would have been VI.

In addition, during the plea proceeding itself, the

government attorney stated that, "[u]nder the plea agreement

. . . I believe the total offense level would be 32" -- an

indication that the agreement did not contemplate career-offender

status. The government attorney also indicated that the career-

offender enhancement was irrelevant, stating that, "in light of

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the agreement" and departure motion, defense counsel had no reason

to object to the PSR's career-offender determination. See supra

Section I.C. Indeed, defense counsel did not object to that

interpretation of the parties' agreement; he did not interject to

clarify, for example, that career-offender status was pertinent,

albeit subsumed within the thirty-five-year recommendation.

In his reply brief, Bartolomeo criticizes the

government's suggestion that defense counsel's failure to object

to the career-offender classification "shows the irrelevance of

[that] designation" to the sentence. Bartolomeo claims that, to

the contrary, his counsel did not object because it was "well-

settled in this Circuit that the Petitioner's objections to the

Petitioner's predicate offenses would have been futile." The

question for us, however, is not defense counsel's actual

motivation for acquiescing to the prosecutor's statement -- a

matter of speculation -- but whether the habeas court clearly erred

in drawing the inference urged by the government. It did not.

Bartolomeo also highlights the provision that was added

to his plea agreement after its first iteration, in which he was

granted the right "to petition the Court, pursuant to 28 U.S.C.

§ 2255, at any time for application of any future decision, ruling,

change in law or change in the Sentencing Guidelines, which may

result in a reduction in the total time of the Defendant's

incarceration." He asserts in his appellate brief that he was

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"stunned that his two prior assault convictions would render him

a career offender" and states that he "insisted" on including this

new provision, Paragraph 8(c), "to afford him the ability to later

challenge his sentence if circumstances afforded him grounds to do

so."

But the plea agreement does not indicate that Paragraph

8(c) was added to the agreement with Bartolomeo's career-offender

status in mind; it could apply to the drug quantity table that

produced his BOL of 32 -- a sentencing component that was

referenced in the plea agreement. Thus, even if the recommendation

for a thirty-five-year term of imprisonment sprung from a

Guidelines starting point, the agreement and motion do not show

that starting point as necessarily the career-offender range.

Bartolomeo also makes the slightly different argument

that Section 8(c) -- preserving his ability to benefit from changes

in Guidelines law -- demonstrates that the thirty-five-year term

has two discrete segments: the applicable Guidelines sentence and

the departure pursuant to U.S.S.G. § 4A1.3(e) (1997). From that

premise, he claims that he was harmed by the career-offender error

in the Guidelines segment of his sentence. However, as our

discussion above demonstrates, the habeas court supportably found

that "petitioner's career offender status . . . is entirely absent

in the plea agreement and joint motion for upward departure" --

i.e., the court determined that the recommended sentence would

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have been the same whether the guideline range was 151-188 months

or, with the career-offender enhancement, 262-327 months. 316 F.

Supp. 3d at 547.

The remaining question is whether Bartolomeo's career-

offender status also was "entirely absent" from the sentencing

court's decision to impose the recommended thirty-five-year term.

2. The Sentencing Proceeding

Bartolomeo is certainly correct that the sentencing

court gave attention to the Guidelines calculation during each

portion of the joint proceeding. Before accepting Bartolomeo's

plea, the court confirmed that Bartolomeo understood that his

guideline range -- with the career-offender designation -- would

be "21 years and some months to 25 years and some months." See

supra Section I.C.1. The court also ascertained during the plea

colloquy that the career-offender guideline may be applied at

sentencing without notice to a defendant and that, in this case,

Bartolomeo had not contested the PSR's assessment that he was a

career offender. The court revisited the Guidelines details at

the outset of the sentencing portion of the proceeding, again

reviewing the elements -- including career-offender status -- that

produced the 262- to 327-month GSR.

Despite this attention to the Guidelines, we see no clear

error in the habeas court's finding that the sentencing judge

accepted the proposed thirty-five-year term without regard for the

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term of imprisonment that would have otherwise applied -- i.e.,

without regard to the length of the departure. The sentencing

court's focus on the Guidelines was in keeping with its obligation

to begin with that generalized calculation before moving on to

determine the appropriate sentence for the particular defendant in

the context of the case before it. Indeed, before embarking on

the Guidelines math in the sentencing portion of the hearing, the

court, in effect, previewed the likelihood that it would disregard

the calculation: "[T]hough I'm going to do the sentencing guideline

calculations, I am disposed to depart upward on the grounds of the

joint motion." In other words, the court explained, it would

determine the sentence prescribed by the Guidelines, "but [the]

sentence will be based on the motion," not the "calculations."

Bartolomeo points to the Statement of Reasons page of

the sentencing court's formal Judgment as evidence that the

Guidelines played a role in the court's decision. That document

inconsistently reports Bartolomeo's TOL as 32 -- i.e., the offense

level without career-offender status -- but lists the CHC (VI) and

guideline range (262-327 months) applicable to Bartolomeo as a

career offender. Neither the recording of the career-offender

data nor the evident error in the corresponding TOL aids

Bartolomeo's appeal. As Bartolomeo emphasizes, the court was

required to calculate the Guidelines range and inform him of it.

The court's having done so does not demonstrate that Bartolomeo's

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career-offender status affected its decision to impose the thirty-

five-year term.15

Bartolomeo's complaint that a nineteen-to-twenty-two-

year departure is a disproportionate increase over the correct

guideline range -- and his career-offender status therefore must

have played a role -- falls flat when that increase is juxtaposed

with the risk he faced of a substantial additional term of

imprisonment if he had been prosecuted for an intentional murder.

Bartolomeo additionally contends that the parties' choice of a

non-binding sentencing recommendation, see Fed. R. Crim P.

11(c)(1)(B), refutes the notion that he received a fixed thirty-

five-year sentence independent of his GSR. However, we fail to

see how the sentencing judge's authority to reject the parties'

proposed term of imprisonment tells us whether the judge relied on

Bartolomeo's career-offender status when it decided to impose the

agreed-upon thirty-five-year sentence. As our discussion above

makes clear, that is a factual question necessarily answered

through a close review of the record.

In sum, the habeas court did not clearly err in finding

that Bartolomeo "has not shown a reasonable probability that his

15
Bartolomeo's assertion that he would not have accepted the
thirty-five-year sentence recommendation but for his career-
offender designation is beside the point. Our task is to examine
the court's rationale for imposing the term, not Bartolomeo's
reasons for accepting it.

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sentence would have been different absent [the career-offender]

designation." 316 F. Supp. 3d at 548. We therefore affirm the

court's denial of Bartolomeo's petition seeking to reduce his

sentence.

So ordered.

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