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.- 4 -
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'
- 5 -
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.
- 9 -
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).
- 14 -
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.
- 31 -
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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