United States Court of Appeals
For the First Circuit
No. 24-1524
UNITED STATES,
Appellee,
v.
REY DAVID FULCAR,
Defendant, Appellant.
APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF MASSACHUSETTS
[Hon. Denise J. Casper, U.S. District Judge]
Before
Barron, Chief Judge,
Kayatta and Rikelman, Circuit Judges.
Inga L. Parsons for appellant.
Alexia R. De Vincentis, Assistant United States
Attorney, with whom Leah B. Foley, United States Attorney,
was on brief, for appellee.
July 6, 2026
BARRON, Chief Judge. Rey David Fulcar ("Fulcar")
challenges his three federal convictions, each of which resulted
from his pleading guilty to the underlying charges. He contends
that his guilty pleas to two of the charged offenses -- one for
being a prohibited person in possession of a firearm and ammunition
in violation of 18 U.S.C. § 922(g)(1) and one for possession with
intent to distribute certain drugs in violation of 21 U.S.C.
§ 841(a)(1) -- must be vacated because those pleas were unknowing
and involuntary. He further argues that his firearm-possession
conviction must be reversed because the Second Amendment to the
United States Constitution bars it. In addition, Fulcar contends
that his sentences for his three federal convictions must be
vacated because the District Court erred in subjecting him to three
enhancements under the United States Sentencing Guidelines
(hereinafter "the Guidelines"). Although we reject most of
Fulcar's contentions, we conclude that it was error to apply one
of these sentencing enhancements -- namely, the enhancement set
forth in what is commonly referred to as the career offender
guideline -- at his sentencing. We nonetheless affirm his
convictions and his sentences because we conclude that the error
in subjecting him to that enhancement was harmless.
I.
On March 1, 2023, a grand jury sitting in the District
of Massachusetts handed up an indictment that charged Fulcar with
- 2 -three counts. The first count charged him with being a prohibited
person in possession of a firearm and ammunition, in violation of
18 U.S.C. § 922(g)(1). The other two counts charged him with
possession with intent to distribute controlled substances, in
violation of 21 U.S.C. § 841(a)(1).1 The first drug-related count
was based on drugs that were found on Fulcar during his arrest in
Boston. The second drug-related count was based on drugs that
were found in Fulcar's home while it was being searched.
On July 3, 2023, Fulcar moved to suppress the evidence
seized from his home, arguing that the search that led to the
seizure violated the Fourth Amendment to the United States
Constitution. The District Court denied the motion after
determining that the search was properly carried out pursuant to
a valid search warrant and that, in any event, the officer
executing the warrant acted in good-faith reliance on it. See
United States v. Leon, 468 U.S. 897, 922 (1984) ("Searches pursuant
to a warrant will rarely require any deep inquiry into
reasonableness, for a warrant issued by a magistrate normally
suffices to establish that a law enforcement officer has acted in
good faith in conducting the search." (citation modified)).
The facts are stated as they appear in the record.
1 See
United States v. McKinney, 5 F.4th 104, 106 n.1 (1st Cir. 2021)
("The facts that follow are taken from the record, particularly
the indictment, plea agreement, presentence report, and sentencing
hearing transcript." (citing United States v. Santa-Soler, 985
F.3d 93, 95 (1st Cir. 2021))).
- 3 -Thereafter, Fulcar filed a motion to dismiss the
firearm-related count. He did so on the ground that § 922(g)(1)
violated the Second Amendment to the United States Constitution
both on its face and as applied to him. The District Court denied
the motion on October 27, 2023.
A little less than two months later, on
December 20, 2023, Fulcar entered unconditional guilty pleas to
all three counts in the indictment. The United States Office of
Probation then prepared a Presentence Investigation Report
("PSR").
In calculating Fulcar's recommended sentencing range
under the Guidelines for each of his convictions, the PSR applied
certain Guidelines sentencing enhancements based on his offense
conduct. Specifically, the PSR applied a four-level enhancement
under § 2K2.1(b)(6)(B) of the Guidelines in determining Fulcar's
total offense level for his § 922(g)(1) conviction. At the time
of sentencing, that enhancement applied when the defendant "used
or possessed any firearm or ammunition in connection with another
felony offense." U.S. Sent'g Guidelines Manual § 2K2.1(b)(6)(B)
(U.S. Sent'g Comm'n 2023) [hereinafter "U.S.S.G."].
The PSR also applied the enhancement under § 2K2.1(a)(2)
to the § 922(g)(1) conviction. Section 2K2.1(a)(2) yields a base
level of twenty-four for a conviction under 18 U.S.C. § 922(g)(1)
when "the defendant committed any part of the instant offense
- 4 -subsequent to sustaining at least two felony convictions of . . . a
controlled substance offense." U.S.S.G. § 2K2.1(a)(2).
In addition, the PSR applied a four-level enhancement
under § 4B1.1(b)(3) of the Guidelines -- which is commonly referred
to as the career offender guideline. The PSR did so in determining
Fulcar's total offense level for his two drug-related convictions.
The career offender guideline's enhancement applies if
the defendant has two or more qualifying prior convictions. Id.
§ 4B1.1(a). That Guideline treats a prior conviction for a
"controlled substance offense" as a qualifying conviction. Id.
Fulcar objected to the application of the enhancement in
§ 2K2.1(b)(6)(B) of the Guidelines on the grounds that he did not
"'use or possess' the firearm/ammunition that was found inside a
bin/container . . . in connection with another felony offense."
Fulcar argued that the firearm in question was "kept inside [his]
dwelling to protect him and his girlfriend at the time and not
used in any way to facilitate the distribution of drugs."
Fulcar objected to the application of both § 2K2.1(a)(2)
and § 4B1.1(b)(3) on the grounds that he only had one qualifying
prior conviction, not two. Specifically, he objected to the PSR's
treatment of his 2008 Massachusetts law conviction for the offense
of possession with intent to distribute "cocaine" as a conviction
for a "controlled substance offense."
- 5 -The District Court rejected Fulcar's objection to the
PSR's application of the career offender enhancement. It also
determined that it did not need to rule on Fulcar's objection to
the PSR's application of the enhancements under § 2K2.1(b)(6)(B)
and § 2K2.1(a)(2) to his § 922(g)(1) conviction because, even if
those enhancements did apply, they would not affect Fulcar's
ultimate Guidelines sentencing range. That was so, according to
the District Court, because Fulcar's three federal convictions had
to be grouped under the Guidelines and his offense level for the
two federal drug-related counts -- which was higher than even the
enhanced total offense level for his conviction for the § 922(g)(1)
offense -- drove the recommended sentencing range under the
Guidelines for all his convictions. See U.S.S.G. §§ 3D1.2, 3D1.3.
The District Court observed, however, that if it did have to reach
the question of whether the firearm enhancement applied, then it
"would have found . . . that it applied here."2
2 The District Court did not explicitly address whether, in
the absence of grouping, it would have found that U.S.S.G.
§ 2K2.1(a)(2) applied to Fulcar's firearm conviction under 18
U.S.C. § 922(g)(1). It is unclear whether this was intentional or
due to a misunderstanding between the parties and the District
Court. Nonetheless, as we will explain, the application of
U.S.S.G. § 2K2.1(a)(2) -- through a cross-reference -- in this
case depends on the application of U.S.S.G. § 4B1.1(b)(3), the
career offender guideline. That is so because § 2K2.1(a)(2)
applies when the defendant "committed any part of the instant
offense subsequent to sustaining at least two felony convictions
of either a crime of violence or a controlled substance offense."
However, § 2K2.1 indicates in its application notes that
- 6 -The District Court determined that the recommended
sentencing range under the Guidelines for Fulcar's three federal
convictions was 151 to 188 months of imprisonment. It ultimately
imposed, however, a below-Guidelines sentence of 96 months of
imprisonment.
In imposing that sentence, the District Court noted that
"whether or not [it] had accepted [Fulcar's] arguments about what
the advisory guideline sentencing range should be, that is, if
[it] had accepted them, [it] would have still reached the same
sentence [that it was] imposing [t]here, having considered all of
the factors under Title 18, United States Code, 3553(a)." The
District Court went on to explain that it would have done so
because that sentence was "a sufficient and reasonable sentence
given all of the sentencing factors, but not greater than
necessary, to achieve all of the goals of sentencing" that it had
reviewed.
"controlled substance offense" is defined in the same way it is
defined in the career offender guideline. U.S.S.G. § 2K2.1 cmt.
n.1. Therefore, the question of whether it would be error to apply
the enhancement under § 2K2.1(a)(2) in this case likely rises and
falls with the analysis of whether it would be error to apply the
career offender guideline. In any event, because our reasons for
finding the application of the career offender guideline harmless
apply equally to any erroneous application of this guideline in
this case, we need not address its application here any further.
- 7 -II.
Fulcar acknowledges that if his unconditional pleas to
his federal convictions that were based on evidence that was seized
during the search of his home were knowing and voluntary, then he
is barred from challenging those convictions on appeal based on
the denial of his motion to suppress the evidence obtained during
that search.3 He contends, however, that he is not so barred
because the District Court did not comply with Rule 11 of the
Federal Rules of Criminal Procedure. He contends that the District
Court did not do so because it failed to ensure that, in entering
those guilty pleas, he understood that he was waiving his ability
to appeal the denial of his motion to suppress.
Fulcar concedes that he did not advance this argument
below. As a result, our review of the asserted error is only for
plain error. See United States v. Williams, 48 F.4th 1, 5 (1st
3 Fulcar does not specify which of the three counts to which
he pleaded guilty he is arguing would be invalidated by a finding
that the District Court erred in failing to inform him that he
could not appeal the motion to suppress if he entered unconditional
pleas. However, Fulcar bases his challenge to the voluntariness
of his pleas on not being informed that he would be unable to
appeal the denial of his motion to suppress the evidence seized
during a search of his home. Given that the evidence seized from
his home -- drugs, a firearm, and ammunition -- formed the basis
of count one, which charged him with being a prohibited person in
possession of a firearm and ammunition in violation of 18 U.S.C.
§ 922(g)(1), and count three, which charged him with possession
with intent to distribute certain drugs in violation of 21 U.S.C.
§ 841(a)(1) based on the drugs found in his home, we read this
first challenge to only be aimed at his guilty pleas to those
counts.
- 8 -Cir. 2022) ("We review an unpreserved Rule 11 claim for plain
error." (citing United States v. Vonn, 535 U.S. 55, 58-59 (2002))).
"To establish plain error," Fulcar must show "that
(1) an error occurred; (2) the error was clear or obvious; (3) the
error affected [the appellant's] substantial rights; and (4) the
error seriously affected the fairness, integrity or public
reputation of the judicial proceedings." United States v. Kitts,
27 F.4th 777, 784 (1st Cir. 2022) (citation modified). Fulcar has
not shown plain error here.
Generally, Federal Rule of Criminal Procedure 11
"defines the contours of the plea hearing" and ensures that a
defendant enters his plea knowingly and voluntarily by requiring
the district court to inform the defendant of the rights that he
is waiving by pleading guilty. Williams, 48 F.4th at 6; see also
Fed. R. Crim. P. 11(b). Fulcar acknowledges that Rule 11 "does
not expressly state that the defendant has to be advised of the
right to appeal a motion to suppress only through a conditional
plea." However, he insists that, even if Rule 11 does not require
such a warning, "due process requires that the plea amount to a
voluntary and intentional relinquishment of a known right."
(Quoting United States v. Cotal-Crespo, 47 F.3d 1, 4 (1st Cir.
1995) (citation modified).)
Fulcar points to no precedent suggesting that, as far as
the knowing and voluntary entry of a guilty plea is concerned, due
- 9 -process imposes requirements beyond those provided by Rule 11.
See United States v. Romero, 906 F.3d 196, 207 (1st Cir. 2018)
(finding defendant could not show supposed error was clear or
obvious because he had "no binding precedent on his side").
Moreover, we have previously linked Rule 11 to the requirements of
due process. See Cotal-Crespo, 47 F.3d at 4. And, in Williams,
we described the "core concerns" of Rule 11 as there having been
"a lack of coercion" in the defendant's decision to plead guilty,
"the defendant's understanding of the charges against him, and the
defendant's 'knowledge of the consequences of the guilty plea.'"
48 F.4th at 6 (quoting Cotal-Crespo, 47 F.3d at 4). We also
declined in that case "to add a new core concern to that
list -- namely, that the defendant must understand that by
proceeding he would be waiving the right to challenge the seizure
of evidence." Id. (citation modified).
It follows that Fulcar has not shown that the District
Court plainly erred by failing to inform him that his unconditional
guilty pleas barred him from challenging the denial of his motion
- 10 -to suppress.4 And so, his challenge to his convictions based on
that failure necessarily falls short.5
III.
Fulcar separately challenges his § 922(g)(1) conviction
on the grounds that the District Court erred by denying his motion
to dismiss the count of the indictment that charged him with
violating that statute. He does so based on New York State Rifle
& Pistol Association, Inc. v. Bruen, 597 U.S. 1 (2022). He argues
4 In his opening brief, Fulcar noted that "[s]ubstantial
briefing and a lengthy motion to suppress argument was held."
During oral argument, Fulcar emphasized the "unique nature" of
this case and seemed to argue it stemmed from the "very extensive"
motion to suppress litigation that preceded the guilty pleas. To
the extent Fulcar meant to argue that the lengthy motion to
suppress litigation counsels in favor of finding the District Court
plainly erred by not specifically advising him he could not appeal
the outcome of the motion, he failed to point to any case
law -- either in his brief or during oral argument -- to support
that contention. That plain-error argument therefore also fails.
See, e.g., United States v. Correa-Osorio, 784 F.3d 11, 21 n.12
(1st Cir. 2015) (explaining that prevailing on plain error requires
clear and binding precedent).
5 Fulcar separately advances a claim of ineffective assistance
of counsel based on his counsel's asserted failure to inform him
that the entry of his guilty plea would preclude him from appealing
the denial of his suppression motion. However, we will address on
direct appeal a claim of ineffective assistance only in the rarest
of cases. See, e.g., United States v. García-Pastrana, 584 F.3d
351, 388 (1st Cir. 2009) ("[T]he proper vehicle for relief for
ineffective assistance of counsel is a motion under 28 U.S.C.
§ 2255, not direct appeal."). In the alternative, Fulcar asks us
to "remand to the district court for a factual hearing on the
matter." We do not think this case calls for such a discretionary
remand, either. See United States v. Colon-Torres, 382 F.3d 76,
85 (1st Cir. 2004) (limiting remand to situations where the record
"contain[s] sufficient indicia of ineffectiveness in the plea
agreements, the PSR, and the transcripts of the change of plea and
sentencing hearings").
- 11 -that, under that precedent, § 922(g)(1) violates the Second
Amendment both on its face and as applied to him, because
"[p]ossessing a firearm within the home is a core right protected
by the Second Amendment," and "[f]or these reasons and the
arguments set forth in detail in" his motion to dismiss filed
below, the § 922(g)(1) count should have been dismissed. (Citing
District of Columbia v. Heller, 554 U.S. 570, 626-30 (2008).)
As we have explained before, however, incorporating by
reference as a practice "has been 'consistently and roundly
condemned,' and any incorporated argument is ordinarily deemed
forfeited." United States v. Orrego-Martinez, 575 F.3d 1, 8 (1st
Cir. 2009) (per curiam) (citation omitted) (quoting Gilday v.
Callahan, 59 F.3d 257, 273 n.23 (1st Cir. 1995)); see also Sleeper
Farms v. Agway, Inc., 506 F.3d 98, 104 (1st Cir. 2007) ("They
purport to incorporate by reference their motion before the
district court. That is not acceptable: this court will only
consider arguments made before this court; everything else is
deemed forfeited." (citation modified)). And while Fulcar does
slightly more than simply incorporate his briefing before the
District Court, he fails to develop any argument as to why Bruen
or Heller renders § 922(g)(1) unconstitutional. See United States
v. Zannino, 895 F.2d 1, 17 (1st Cir. 1990) (noting the "settled
appellate rule that issues adverted to in a perfunctory manner,
unaccompanied by some effort at developed argumentation, are
- 12 -deemed waived"). Significantly, Fulcar does not address the
District Court's primary reason for denying his motion to
dismiss: United States v. Torres-Rosario, the First Circuit
precedent that the District Court determined foreclosed his motion
and survived the Supreme Court's Bruen decision. See 658 F.3d 110
(1st Cir. 2011); cf. Sparkle Hill, Inc. v. Interstate Mat Corp.,
788 F.3d 25, 30 (1st Cir. 2015). We therefore deem waived any
argument that the District Court's ruling on this issue was in
error.
IV.
Fulcar's challenges to his sentences concern the
District Court's application of three sentencing enhancements that
the Guidelines set forth. We review the District Court's
interpretation and application of the Guidelines de novo and its
fact-finding for clear error. See United States v. Carvajal, 85
F.4th 602, 609 (1st Cir. 2023) (quoting United States v.
Ruiz-Huertas, 792 F.3d 223, 226 (1st Cir. 2015)). If the District
Court's alleged error in applying the Guidelines did not affect
the ultimate sentence imposed, then we may affirm the sentence on
that basis alone. See United States v. Marsh, 561 F.3d 81, 86
(1st Cir. 2009).
A.
We begin with Fulcar's challenge to the District Court's
application of the career offender guideline, which in Fulcar's
- 13 -case yields an offense level of thirty-two. U.S.S.G.
§ 4B1.1(b)(3). That Guideline, in relevant part, applies when
"the defendant has at least two prior felony convictions of . . . a
controlled substance offense." U.S.S.G. § 4B1.1(a)(3). The
Guidelines define, in relevant part, a "controlled substance
offense" as "an offense under federal or state law" that "prohibits
the manufacture, import, export, distribution, or dispensing of a
controlled substance (or a counterfeit substance) or the
possession of a controlled substance (or a counterfeit substance)
with intent to manufacture, import, export, distribute, or
dispense." Id. § 4B1.2(b)(1) (emphasis added).
As we noted at the outset, the District Court expressly
stated that it would have imposed the same sentence even if it had
"accepted" Fulcar's arguments "about what the advisory guideline
sentencing range should be." Any error in the Guidelines
calculation would, then, be harmless. See United States v.
Ouellette, 985 F.3d 107, 110 (1st Cir. 2021) ("[W]e have
consistently held that when a sentencing court makes clear that it
would have entered the same sentence regardless of the Guidelines,
any error in the court's Guidelines calculation is harmless.").
But the government makes no argument to us that we must reject
Fulcar's challenge to the application of the career offender
guideline -- or any guideline -- on that basis. Indeed, the
government does not even cite the portion of the sentencing hearing
- 14 -during which the District Court states that it "would have still
reached the same sentence" irrespective of whether it found that
the career offender guideline or any other guideline at issue
applied to Fulcar. Rather, the government urges us to address the
question of whether the career offender guideline applies head-on,
and so, the government necessarily contemplates that it might
receive an adverse ruling on that question.
Often, of course, when the record reveals that an
asserted error is harmless, it makes sense to bypass the question
of whether such an error occurred. But that is not our invariable
practice, and here, because the government neither asks us to
affirm the sentence based on the asserted error having been
harmless nor even identifies the basis in the record for affirming
the sentence because that claimed error was harmless, we think it
prudent to resolve the question about whether there was error that
the government has asked us to resolve.
The issues have been thoroughly briefed and so we have
full adversarial testing. It is also a question of pure law. In
addition, resolving this issue will provide clarity on a recurring
issue of sentencing -- and so one that inevitably bears on plea
negotiations -- in which the current state of our case law is less
than clear. See United States v. Soto-Sanchez, 138 F.4th 81, 90
(1st Cir. 2025).
- 15 -Thus, although, as we will explain, we ultimately
conclude that Fulcar's challenge to the application of the career
offender guideline to him fails on harmless error grounds, we first
assess his contention that the District Court did err in applying
that Guideline enhancement to him. And, as we also will explain,
we agree with Fulcar that the District Court did so err.
1.
The parties agree that the career offender guideline's
enhancement applies only if Fulcar's 2008 Massachusetts law
conviction for the offense of possession of cocaine with intent to
distribute qualifies as a conviction for a "controlled substance
offense" within the meaning of that Guideline. Fulcar contends
that the enhancement does not so apply because the substance that
he was convicted in 2008 of possessing with intent to
distribute -- which Massachusetts law deemed to be "coca leaves"
or a derivative thereof, and which the parties refer to as
"cocaine" -- is not a "controlled substance" within the meaning of
the career offender guideline. As we will explain, we agree with
Fulcar.
2.
The Massachusetts Controlled Substances Act ("MCSA")
identifies various substances as "controlled substances," and it
then assigns each of those substances to a "class" that is
identified by a letter. See Mass. Gen. Laws ch. 94C, § 31. The
- 16 -MCSA classifies "[c]oca leaves" and their derivatives as Class B
substances, id. § 31(Class B)(a)(4); as noted above, the parties
refer to such substances as "cocaine," and we do the same for ease
of reference.6 At the time of Fulcar's 2008 conviction, the MCSA
defined that substance -- in relevant part -- to include
"ecgonine," which the parties agree includes its
derivative: [123I]ioflupane ("ioflupane"). Id. § 31(Class B)(a)(4)
(2008).
Federal law has its own statute, the Controlled
Substances Act ("CSA"), that identifies various substances as
"controlled substances."7 21 U.S.C. §§ 801–904. Rather than
assigning each such substance to a class identified by a letter,
however, the CSA assigns each one to a "schedule" that is
identified by a roman numeral. Id. § 802(6). Like the MCSA, the
CSA also labels as a controlled substance -- under Schedule
II -- "[c]oca leaves" and their derivatives, which the parties
refer to simply as "cocaine." Id. § 812 (Schedule II)(a)(4). At
the time of Fulcar's 2008 Massachusetts law conviction,
Schedule II of the CSA, like the MCSA, defined this group of
6 Mass. Gen. Laws ch. 94C, § 32A sets out the terms of
imprisonment for possession with intent to distribute a Class B
substance.
7 The CSA defines a "controlled substance" as "a drug or other
substance, or immediate precursor, included in schedule I, II,
III, IV, or V of part B of this subchapter." 21 U.S.C. § 802(6).
Part B then goes on to list the five schedules and the
corresponding drugs. Id. § 812.
- 17 -substances to include derivatives of ecgonine, such as ioflupane.
21 C.F.R. § 1308.12(b)(4)(ii) (2008).
As a result, in 2008, when Fulcar was convicted under
Massachusetts law of the offense of possession with intent to
distribute a controlled substance, that conviction clearly was for
an offense that involved "cocaine" under both Massachusetts and
federal law. In 2015, however, things changed. That year,
Schedule II of the CSA was amended to exclude "ioflupane" from the
definition of "cocaine." That substance thus was excluded as of
that time from being a "controlled substance" under the CSA.
21 C.F.R. § 1308.12(b)(4)(ii) (Sept. 11, 2015); Schedules of
Controlled Substances: Removal of [Ioflupane] From Schedule II of
the Controlled Substances Act, 80 Fed. Reg. 54715, 54717
(Sept. 11, 2015). And that exclusion persisted through the time
of Fulcar's sentencing for his three federal convictions at issue
in this appeal, even though the MCSA continued to define "cocaine"
to include ioflupane.
According to Fulcar, ioflupane's exclusion in 2015 from
Schedule II, given that it persisted through the time of his
sentencing for his federal convictions, means that his 2008
Massachusetts law conviction is not a conviction for a "controlled
substance offense" under the career offender guideline. Fulcar
reasons as follows.
- 18 -Fulcar begins by arguing that we must apply what is known
as the categorical approach to determine if his assertedly
qualifying prior conviction -- his 2008 Massachusetts law
conviction -- is for a "controlled substance offense" under the
career offender guideline. Under that approach, we must presume
that this prior conviction "rested upon nothing more than the least
of the acts criminalized by the statute of conviction." Thompson
v. United States, 64 F.4th 412, 419 (1st Cir. 2023) (citation
modified). And, under that same approach, we may determine what
those acts are solely by focusing on "the elements of the
[assertedly qualifying predicate] crime -- i.e., the constituent
parts of the crime's legal definition (the things the prosecution
must prove beyond a reasonable doubt to sustain a
conviction) -- and not how a given defendant actually perpetuated
[that] crime." United States v. García-Cartagena, 953 F.3d 14, 18
(1st Cir. 2020) (citation modified).
Thus, Fulcar reasons that we must presume that his 2008
Massachusetts law conviction was for the offense of possession
with intent to distribute ioflupane, regardless of whether, in
committing the underlying offense, he actually possessed that
substance rather than a different one that the MCSA also deemed to
be "cocaine" but that the CSA did not exclude from its definition
of "cocaine" at the time of his federal sentencing for his three
federal convictions. As a result, Fulcar argues that we must
- 19 -presume that he was convicted of possession with intent to
distribute a substance that, as of the time of his sentencing for
those three federal convictions, was not, per the CSA, "controlled"
under federal law.
The government does not disagree with Fulcar's arguments
concerning the categorical approach. But Fulcar's challenge to
the application of the career offender guideline also depends on
two additional steps in his argument about what qualifies as a
"controlled substance" under that Guideline, each of which the
government does dispute.
The first of those steps concerns the body of
law -- state or federal -- under which a substance must be
"controlled" to qualify as a "controlled substance" within the
meaning of the career offender guideline. Fulcar contends that
the Guideline directs us to conclude that a substance is so
"controlled" only if it is "controlled" by federal law -- even
when, as in his case, the assertedly qualifying prior conviction
is for a state offense.
The second of those steps concerns the time for
determining whether a substance is controlled. Here, Fulcar
contends that the career offender guideline directs us to look at
the time that the career offender guideline is applied to the
defendant -- and thus, in his case, to the time that he was
sentenced for the three federal convictions at issue in this
- 20 -appeal. In other words, he contends that the Guideline directs us
not to look at any other time, such as the time of conviction for
the alleged predicate crime, which in his case would have been
2008, when he was convicted of the assertedly qualifying
Massachusetts law offense.
The government does not dispute that if Fulcar is right
about these last two steps in his argument, then his 2008
Massachusetts law conviction is not a conviction for a "controlled
substance offense" under the career offender guideline. The
government acknowledges that, at the time of Fulcar's sentencing
for his three federal convictions at issue in this appeal, the
body of law that defined the substances that were "controlled"
under federal law did not define ioflupane to be such a substance.
The government contends, however, that, in the case of
an assertedly qualifying prior state law conviction, a "controlled
substance" under the career offender guideline includes substances
that are controlled under the law of the relevant state, whether
or not those substances are also controlled under federal law.
Thus, the government argues, even if Fulcar is right about the
career offender guideline's time-of-federal-sentencing temporal
orientation, Fulcar's 2008 Massachusetts law conviction is still
a conviction for a "controlled substance offense" under the career
offender guideline. And that is so, according to the government,
because Massachusetts, per the MCSA, "controlled" ioflupane not
- 21 -only when Fulcar's 2008 conviction was entered but also up through
the time that Fulcar was sentenced for his federal convictions,
which is the time when that Guideline was applied to him.
The government also contends that, even if we must look
only to the body of law that defines what substances the federal
government controls, we still must look to that body of law as it
stood at the time of the entry of the assertedly qualifying prior
conviction and not at the time of the career offender guideline's
application. The government then contends that we must therefore
look to 2008, when Fulcar was convicted under Massachusetts law,
and not to when he was sentenced for the three federal convictions
at issue in this appeal. Thus, the government argues, even on
Fulcar's understanding of what the relevant body of law is that
determines whether a substance is "controlled," Fulcar's 2008
conviction is still a conviction for a "controlled substance
offense" under the career offender guideline. And that is because,
as the government points out, even Fulcar agrees that in 2008,
ioflupane was "controlled" under federal law.
During oral argument, the government urged us to revisit
our precedent that bears on the temporal point. See United States
v. Abdulaziz, 998 F.3d 519, 523 (1st Cir. 2021) (adopting a
time-of-federal-sentencing approach to the definition of
"controlled substance offense" under the Guidelines). It contends
that the "core" and "sole" reasoning on which that precedent relied
- 22 -has been rejected by an intervening Supreme Court case. See Brown
v. United States, 602 U.S. 101, 123 (2024) (adopting a
time-of-prior-offense approach to the definition of "serious drug
offense" under the Armed Career Criminal Act, 18 U.S.C.
§ 924(e)(2)(A)(ii)).
We agree with the government that there is a need to
clarify our law in this area. We therefore begin with the
temporal-orientation issue. As we will explain, however, we
conclude that Fulcar has the better of that argument. We then
address the government's contention about the body of law that
defines what substances are controlled -- as here, too, our law
would benefit from clarification. And here, too, we conclude that
Fulcar has the better of the argument. Thus, we conclude that
Fulcar is right that the District Court erred by subjecting him to
the career offender guideline's enhancement. Nonetheless, as we
will explain, we still must reject his challenge to his sentences
insofar as that challenge is based on that error because we
conclude that the error was harmless.
3.
Starting with the temporal-orientation issue, the
government acknowledges that a panel of this court held in
Abdulaziz that in applying an enhancement applicable when an
offense was committed "subsequent to sustaining at least two felony
convictions of either a crime of violence or a controlled substance
- 23 -offense," "we must look to the version of those drug schedules
that were 'in effect'" at the time of sentencing for the federal
offense.8 998 F.3d 519, 521, 523 (1st Cir. 2021) (quoting United
States v. Rodriguez, 630 F.3d 39, 42 (1st Cir. 2010)). The
government contends, however, that the Supreme Court's subsequent
decision in Brown, which addressed a similar timing issue under
the Armed Career Criminal Act ("ACCA"), undermines Abdulaziz. As
a result, the government argues, Brown strips Abdulaziz of its
controlling force under the law of the circuit doctrine. See
United States v. Guzmán, 419 F.3d 27, 31 (1st Cir. 2005)
(describing instances in which "authority that postdates the
original decision, although not directly controlling, may
nevertheless offer a compelling reason for believing that the
former panel, in light of new developments, would change its
collective mind").
In the government's view, Abdulaziz's rationale depended
on the assumption that ACCA itself was oriented forward to the
time of federal sentencing rather than backward to the time of the
assertedly qualifying predicate conviction. See Abdulaziz, 998
F.3d at 526-27. But, the government points out, Brown held the
8 Although Abdulaziz concerned a different Guidelines
enhancement, U.S.S.G. § 2K2.1(a), the applicability of that
enhancement -- and the court's reasoning -- turned on § 4B1.2(b)'s
definition of "controlled substance," the same provision we
interpret here. United States v. Abdulaziz, 998 F.3d 519, 523
(1st Cir. 2021).
- 24 -opposite based on its determination that "ACCA is a recidivist
statute that gauges what a defendant's 'history of criminal
activity' says about his or her 'culpability and dangerousness.'"
Brown, 602 U.S. at 111 (quoting McNeill v. United States, 563 U.S.
816, 823 (2011)). In that regard, the government points out that
the Court explained in Brown that the "history of criminal
activity" with which ACCA is concerned "does not 'cease to exist'
merely because the crime was later redefined." Id. at 113-14
(quoting McNeill, 563 U.S. at 823).
The government is right that Abdulaziz treated the
timing question that the career offender guideline poses as
"analogous to the question of what ACCA's criteria were for
determining what constituted 'a serious drug offense.'" 998 F.3d
at 526. Moreover, we explained in Abdulaziz that "there is
nothing . . . strange about looking to federal law as it exists at
the time of a defendant's federal sentencing to determine the
criteria that a potentially applicable federal sentencing
enhancement uses to determine whether the enhancement must be
applied at that sentencing." Id. at 527.
Abdulaziz did offer other reasons for its resolution of
the timing issue. Id. at 528-29. Nonetheless, we assume without
deciding that, given Brown, Abdulaziz's rationale no longer holds
up. Accordingly, we consider the timing issue afresh. But, as we
will next explain, we still conclude that the appropriate temporal
- 25 -focus under the career offender guideline is the time of the
defendant's federal sentencing and not the time of the defendant's
assertedly qualifying prior conviction.
a.
Brown did explain that ACCA's temporal orientation was
backward to the time of the prior conviction because ACCA was an
anti-recidivist statute. See 602 U.S. at 111. But that was not
the whole of Brown's reasoning.
In response to one of the arguments by the defendants
for why ACCA must be construed to be oriented to the time of the
measure's application at federal sentencing, Brown addressed what
is known as the reference canon. 602 U.S. at 115-16. It explained
that, per that canon, "a reference 'to another statute by specific
title or section number' . . . 'in effect cuts and pastes the
referenced statute as it existed when the referring statute was
enacted, without any subsequent amendments.'" Id. at 116 (quoting
Jam v. Int'l Fin. Corp., 586 U.S. 199, 209-10 (2019)). By
contrast, the Court explained, in accord with that same canon, a
reference to "general law" "incorporates the law on that subject
as it exists whenever a question under the statute arises." Id.
(emphasis omitted) (quoting Jam, 586 U.S. at 209).
Brown then rejected the defendant's contention that
ACCA's express reference to section 102 of the CSA was a reference
to "general law" for purposes of the reference canon. Id. Rather,
- 26 -Brown explained, "it is hard to see the phrase 'as defined in
section 102 of the Controlled Substances Act,'" 21 U.S.C. § 802,
"as anything but a specific reference." 602 U.S. at 116 (quoting
18 U.S.C. § 924(e)(2)(A)(ii)); see also 21 U.S.C. § 802(6) ("The
term 'controlled substance' means a drug or other
substance . . . included in schedule I, II, III, IV, or V of part B
of this subchapter.").
Thus, Brown determined that, precisely because of ACCA's
express cross-reference to the CSA, the reference canon did not
support the defendant's argument that ACCA was oriented forward to
the time of sentencing rather than backward to the time of the
assertedly qualifying predicate conviction. 602 U.S. at 116.
Unlike ACCA, however, the career offender guideline does not make
express reference to the CSA. See U.S.S.G. § 4B1.1(a)(3). It
instead refers only generally to a "controlled substance."9 Id.;
see also id. § 4B1.2(b). Brown therefore suggests that the
reference canon points in favor of construing the phrase
"controlled substance" in the career offender guideline to take on
the meaning of that phrase under the general body of law to which
that phrase refers at the time that the question about the phrase's
meaning arises rather than at any earlier time.
Although § 4B1.2(b)'s definition of "controlled substance
9
offense" does expressly reference two provisions from the United
States Code out of the CSA, 46 U.S.C. §§ 70503(a) and 70506(b),
those express references are not at issue in this case.
- 27 -The Fifth Circuit has reached this same conclusion in
the wake of Brown.10 See United States v. Minor, 121 F.4th 1085,
1090-92 (5th Cir. 2024). It explained that, under the reference
canon, "a statute that refers to another statute by specific title
or section number in effect cuts and pastes the referenced statute
as it existed when the referring statute was enacted, without any
subsequent amendments." Id. at 1090 (quoting Jam, 586 U.S. at
209-10). It therefore concluded that the Guidelines' inclusion of
only the general term "controlled substance" rather than an
10Other circuits that have considered this question
post-Brown have reached the opposite conclusion. However, those
cases do not consider how the reference canon influences the
interpretation of the Guidelines as compared to ACCA. Those cases
also opted to follow pre-Brown circuit precedent that held the
relevant reference point was the time of conviction for the
predicate crime and did not read Brown as requiring those
precedents to be overturned. See, e.g., United States v. Nelson,
151 F.4th 577, 583 (4th Cir. 2025) (reading Brown as "leaving
[them] free to decide between [the time-of-sentencing] approach
and the time-of-conviction approach" and "recogniz[ing] that such
determination was long ago made by [their] court" in favor of the
"time-of-conviction approach"); United States v. Drake, 126 F.4th
1242, 1245-46 (6th Cir. 2025) (declining to read a footnote in
Brown distinguishing between ACCA and the Guidelines as allowing
the court to depart from pre-Brown circuit precedent that adopted
the time-of-conviction approach (citing Brown v. United States,
602 U.S. 101, 120 n.7 (2024) (explaining that "there is reason to
doubt that the Guidelines practice is relevant" to ACCA "because
Congress has expressly directed courts to apply the Guidelines in
effect on the date the defendant is sentenced" while "ACCA contains
no similar instruction" (citation modified)))); United States v.
Piett, No. 23-13197, 2025 WL 2156749, at *3 (11th Cir. July 30,
2025) ("We conclude that Piett's argument is foreclosed by
. . . our prior holding that a controlled substance under
§ 4B1.2(b)'s definition of 'controlled substance offense' is, for
prior state offenses, a drug regulated by state law at the time of
the conviction.").
- 28 -explicit cross-reference to the CSA "weighs in favor of applying
the definition of that term as it exists whenever a question under
the statute arises -- i.e., sentencing for the instant offense,"
and not the date of the predicate conviction. Id. (citation
modified). And so, the Fifth Circuit explained, precisely because
of ACCA's cross-reference to the CSA, "the reference canon operated
differently in Brown than it does" in the context of the career
offender guideline.11 Id. at 1092.
Of course, the career offender guideline, like ACCA, is
concerned with recidivist behavior. So, in that respect, the
career offender guideline could be understood, like ACCA, to be a
"recidivist" measure "that gauges what a defendant's 'history of
criminal activity' says about his or her 'culpability and
dangerousness.'" Brown, 602 U.S. at 111 (quoting McNeill, 563
U.S. at 823). For that reason, the career offender guideline could
be thought to be similarly aimed at tying the sentencing
11We note that there was a dissent in Minor. See 121 F.4th
1085, 1094 (5th Cir. 2024) (Duncan, J., dissenting). In addition
to raising the contentions we respond to in this opinion, the
dissent argued that "a time-of-sentencing approach would yield
absurd results," because two defendants with the same predicate
conviction sentenced on either side of a change to the CSA would
render one a career offender, but not the other. Id. at 1095
(quoting United States v. Lewis, 58 F.4th 764, 772 (3d Cir. 2023)).
As we have explained, however, "this kind of differential treatment
between otherwise similarly situated defendants often arises when
courts apply -- as they ordinarily must -- the Guidelines that are
operative at the time of sentencing." Abdulaziz, 998 F.3d at 529.
We fail to see how such an ordinary differential would be an absurd
result.
- 29 -enhancement that it sets forth to the defendant's behavior as it
was viewed in the eyes of the law at the time that the defendant
was convicted of the predicate crime.
However, the Guidelines account for a defendant's
history of criminal activity even when those past convictions do
not qualify as predicate crimes under the career offender guideline
in the calculation of a defendant's Criminal History Category.
See, e.g., U.S.S.G. § 1B1.1(a)(6). Nor is it otherwise clear that
the United States Sentencing Commission ("Commission"), in
promulgating the career offender enhancement, has chosen to focus
on the inherent danger of lawbreaking over the danger Congress
assigns to specific drugs.
Furthermore, we do not understand Brown to hold that a
measure's anti-recidivist purpose is in and of itself necessarily
dispositive of its temporal reference point. Instead, as Brown
acknowledged, "[t]he reference canon can be a helpful tool." 602
U.S. at 116. And, as we have already explained, the reference
canon points in a different temporal direction in the context of
the career offender guideline than it does in the context of ACCA
precisely because the career offender guideline does not have an
express cross-reference to the CSA or any other federal measure
defining what a controlled substance is. Instead, it references
only a general term, "controlled substance."
- 30 -Notably, in analyzing how the reference canon applies to
ACCA, Brown did not explain why, despite the express
cross-reference to the CSA, ACCA was oriented to the time of the
prior conviction rather than, per the reference canon, the time of
ACCA's enactment of the cross-reference. Cf. id. (acknowledging
that a specific reference, like the one in ACCA, "in effect cuts
and pastes the referenced statute as it existed when the referring
statute was enacted, without any subsequent amendments," without
explaining why it was rejecting that reference point (quoting Jam,
586 U.S. at 209-10)). Nor did it directly address the import of
the fact that the CSA itself operates through schedules that may
be changed administratively. See 21 U.S.C. § 811 (explaining the
Attorney General's authority to modify the drug schedules). Thus,
we do not understand Brown to hold that the reference canon is not
helpful, even when triggered, in construing any measure that has
an anti-recidivist purpose.
We also note that the Commission's choice not to make
the kind of express reference that Congress made in ACCA aligns
with the fact that, as Brown itself pointedly recognized, the
Guidelines are oriented toward the time of their application rather
than any earlier time. Indeed, in distinguishing the Guidelines
from ACCA, Brown explained that "there is reason to doubt that the
Guidelines practice is relevant here . . . because Congress has
expressly directed courts to apply the Guidelines 'in effect on
- 31 -the date the defendant is sentenced'" while "ACCA contains no
similar instruction." 602 U.S. at 120 n.7 (quoting 18 U.S.C.
§ 3553(a)(4)(A)(ii)); see also Minor, 121 F.4th at 1092 ("Because
ACCA and the Guidelines differ in key ways . . . we understand
that Brown does not dictate the outcome in the case before us.").
b.
For all these reasons, we conclude, like the Fifth
Circuit, that the term "controlled substance" in the career
offender guideline is a reference to a general body of law defining
what the substance is that can change over time.12 Accordingly,
we conclude that the term takes its meaning from the way that term
is defined at the time of the career offender guideline's
application to the defendant -- and so at the time of his
sentencing for the underlying federal offenses.13
12 We also note that this interpretation of the career offender
guideline is not contrary to our interpretation of
section 237(a)(2)(B)(i) of the Immigration and Nationality Act,
which makes "[a]ny alien who at any time after admission has been
convicted of a violation of . . . any law or regulation of a
State . . . relating to a controlled substance (as defined in
section 802 of Title 21) . . . deportable," as adopting a
time-of-conviction approach. 8 U.S.C. § 1227(a)(2)(B)(i). That
measure, like ACCA, contains an express cross-reference to the
CSA. See Dor v. Bondi, 161 F.4th 1, 3 (1st Cir. 2025) (noting
that § 1227(a)(2)(B)(i) "references the federal definition of a
'controlled substance,' as defined by the [CSA] at 21 U.S.C.
§ 802").
13 We note that when the sentencing guideline in question
changes between the commission of the federal offense and
sentencing for the federal offense such that the career offender
guideline then would apply even though it would not have applied
- 32 -4.
We come, then, to the government's contention about the
body of law that determines whether a substance is a "controlled
substance" under the career offender guideline. That question
concerns whether that body of law is only federal or instead is
either state or federal law. As with the temporal issue, we -- and
other circuits -- have addressed this issue before.
Seven circuits have found that in the case of a predicate
state offense either state or federal law can define what
constitutes a "controlled substance" under the Guidelines. See
United States v. Lewis, 58 F.4th 764, 769 (3d Cir. 2023); United
States v. Ward, 972 F.3d 364, 374 (4th Cir. 2020); United States
v. Jones, 81 F.4th 591, 599 (6th Cir. 2023), cert. denied, 144
S. Ct. 611 (2024); United States v. Ruth, 966 F.3d 642, 654 (7th
Cir. 2020); United States v. Henderson, 11 F.4th 713, 718 (8th
Cir. 2021); United States v. Jones, 15 F.4th 1288, 1292 (10th Cir.
2021); United States v. Dubois, 94 F.4th 1284, 1296 (11th Cir.
2024), vacated on other grounds, 145 S. Ct. 1041, reinstated, 139
at the time the federal offense was committed, we, as is customary,
apply the Guideline in effect at the time of the commission of the
federal crime. See United States v. Maldonado, 242 F.3d 1, 5 (1st
Cir. 2001) ("[W]e ordinarily employ the guidelines in effect at
sentencing only where they are as lenient as those in effect at
the time of the offense; when the guidelines have been made more
severe in the interim, the version in effect at the time of the
crime is normally used, as a matter of policy and to avoid any
hint of ex post facto increase in penalty." (citing United States
v. Harotunian, 920 F.2d 1040, 1041-42 (1st Cir. 1990))).
- 33 -F.4th 887, 889 (11th Cir. 2025). By contrast, three circuits have
determined that "controlled substance" in the Guidelines is
defined even with respect to a predicate state offense with
reference to federal law exclusively. See United States v.
Townsend, 897 F.3d 66, 71 (2d Cir. 2018); United States v.
Gomez-Alvarez, 781 F.3d 787, 793-94 (5th Cir. 2015) (interpreting
analogous reference to "controlled substance" in the application
note to U.S.S.G. § 2L1.2); United States v. Bautista, 989 F.3d
698, 702 (9th Cir. 2021). We join the latter half of this circuit
split for the reasons we will next explain.
a.
In United States v. Crocco, the defendant, like Fulcar,
challenged the application of the career offender guideline based
on a prior predicate conviction for a violation of a state law
prohibiting the possession of what was asserted to be a "controlled
substance" under the career offender guideline. 15 F.4th 20, 21
(1st Cir. 2021). That defendant, like Fulcar, also contended that
the conviction did not qualify as one for an offense involving a
"controlled substance" under that Guideline because the state law
offense defined the relevant contraband -- there, marijuana -- to
include a substance -- there, hemp -- that was not a "controlled
substance" within the meaning of federal law, as reflected in the
CSA's drug schedules. Id. at 25.
- 34 -We explained in Crocco that our review was merely for
plain error because the defendant had not preserved the challenge
below and observed that the legal question was unsettled in our
circuit and that the other courts of appeals were split on the
issue. Id. at 27. We further explained that because the case law
was unsettled, any error as to whether the career offender
guideline referred only to substances controlled under federal law
would not have been plain or obvious. Id. at 24.
Nonetheless, we noted that "[b]ecause we [were]
interpreting the federal sentencing guidelines and utilizing the
categorical approach (a creation of federal case law)," the
"federally based approach" advanced by the Second, Fifth, and Ninth
Circuits was "appealing." Id. at 23 (referring, respectively, to
Townsend, 897 F.3d at 68, 71; Gomez-Alvarez, 781 F.3d at 793-94;
Bautista, 989 F.3d at 702). We also explained that "federal courts
cannot blindly accept anything that a state names or treats as a
controlled substance" without "turn[ing] the categorical approach
on its head by defining [a controlled substance] as whatever is
illegal under the particular law of the State where the defendant
was convicted." Id. (second alteration in original) (quoting
Esquivel-Quintana v. Sessions, 581 U.S. 385, 393 (2017)). We
pointed out, as well, that resorting to a dictionary to define
controlled substance only further begged the question and risked
inconsistency based on the chosen dictionary. Id. at 23-24.
- 35 -The government now asks us to reject the implication of
Crocco's dicta. It asks us to hold instead that the career
offender guideline is clear in the case of a predicate state
offense in referring to a substance that the relevant state
controls, even if the federal government does not itself control
that substance. We decline to do so.
b.
Interestingly, the government appears, in advancing its
position on this issue, to emphasize the very point that we
concluded undermined its argument about the temporal-orientation
issue -- namely, that the career offender guideline, unlike ACCA,
does not refer to a specific provision of federal law in referring
to a "controlled substance offense." We can see why the government
would want to emphasize that feature of the Guideline's text here.
If that text did refer to such a provision, then state law could
not determine whether a substance is "controlled" for purposes of
the career offender guideline.
It does not follow from the fact that the career offender
guideline contains no such cross-reference, however, that the
government's state-law-inclusive position is right. Of course,
just as the term "apple" encompasses all varieties, so, too, one
might think, would the term "controlled substance," such that a
substance "controlled" by a state would be considered no less a
"controlled substance" than a substance "controlled" by the
- 36 -federal government. But there is good reason for us to reject
such an ordinary-meaning-based resolution of the interpretive
question given the Supreme Court's decision in Jerome v. United
States, 318 U.S. 101 (1943).
There, the Court construed the federal Bank Robbery Act,
which provided in relevant part that "whoever shall enter or
attempt to enter any bank . . . with intent to commit in such bank
or building . . . any felony or larceny, shall be fined not more
than $5,000 or imprisoned not more than twenty years, or both."
Bank Robbery Act, 12 U.S.C. § 588b (1934) (codified as amended at
18 U.S.C. § 2113). The Court thus had to decide whether the
statute, in referring to "any felony," was referring to any such
offense under federal or state law or only to any such offense
under federal law. See Jerome, 318 U.S. at 102.
One might have thought that, as a matter of plain text,
the answer was clear enough, given that the ordinary meaning of
the general word "felony" would encompass an offense of that kind
under either state or federal law. But the Court rejected that
conclusion. Id.
The Court acknowledged that "[a]t times it has been
inferred from the nature of the problem with which Congress was
dealing that the application of a federal statute should be
dependent on state law." Id. at 104. It went on to explain,
though, that "we must generally assume, in the absence of a plain
- 37 -indication to the contrary, that Congress when it enacts a statute
is not making the application of the federal act dependent on state
law." Id.
The Court explained that this assumption was "based on
the fact that the application of federal legislation is
nationwide," and it pointed to both a "desirability of uniformity"
and the fact that "at times . . . the federal program would be
impaired if state law were to control" as reasons to prefer an
exclusively federal definition. Id. (first citing United States
v. Pelzer, 312 U.S. 399, 402 (1941); and then citing Seaboard Air
Line Ry. v. Horton, 233 U.S. 492, 503 (1914)). The Court on that
basis adopted a presumption that the Act's use of "felony" referred
to federal law only, and the Court then went on to conclude that
the Act did not otherwise evince an intent to encompass state
offenses sufficient to overcome the presumption. Id. at 106-08.
We see no reason to opt for a different interpretive
approach here.14 Jerome did concern the proper interpretation of
Jerome v. United States articulated a third consideration
14
that, in that case, counseled against concluding that "felony"
incorporated state law. 318 U.S. 101, 105 (1943). The Supreme
Court noted that, given the double jeopardy clause of the Fifth
Amendment, "courts should be reluctant to expand" defined offenses
"beyond the clear requirements of the terms of the statute" when
Congress is "creating offenses which duplicate or build upon state
law." Id. The career offender guideline defines a controlled
substance offense to include state offenses, thereby negating this
concern here. However, there is no indication that the Jerome
presumption requires a finding that all of Jerome's considerations
- 38 -a federal criminal statute rather than a federal sentencing
guideline. Id. at 101-02. But, in both instances, we are
construing the handiwork of a federal lawmaking body in the federal
criminal law context.
We also recognize that the career offender guideline,
unlike the statute in Jerome, makes clear that it does encompass
state law offenses. See U.S.S.G. § 4B1.2(b) ("The term 'controlled
substance offense' means an offense under federal or state
law . . . ."). But the text of the Guideline merely provides that
a "controlled substance offense" is an "offense under federal or
state law" that "prohibits the manufacture, import, export,
distribution, or dispensing of a controlled substance (or a
counterfeit substance) or the possession of a controlled substance
(or a counterfeit substance) with intent to manufacture, import,
export, distribute, or dispense." Id. (emphasis added). The
career offender guideline thus makes clear that the question is
not what constitutes an "offense." The question is whether the
unadorned phrase "controlled substance" is referring to a
substance that only the federal government controls or also to one
that a state controls.
be present. Indeed, the Court indicated in Jerome that the double
jeopardy consideration simply "g[ave] additional weight" to its
holding. Id.
- 39 -To that same point, we note that, in many contexts,
Congress has chosen to permit state offenses to trigger criminal
liability only if they have certain attributes that are defined
solely by federal law. See, e.g., 18 U.S.C. § 922(g)(1) (placing
criminal restrictions on "any person . . . who has been convicted
in any court of, a crime publishable by imprisonment for a term
exceeding one year" (emphasis added)). We thus see no reason why
the Jerome presumption would not apply as a tool to aid our
resolution of what "controlled substance" means here.
c.
The government does argue that the Jerome presumption is
just a presumption and thus that it "gives way to 'a plain
indication' that the application of federal law depends on state
law." (Quoting Ward, 972 F.3d at 373-74.) The government then
further states that "based on Section 4B1.2(b)'s context and
history . . . this Court can be 'confident'" that the Jerome
presumption is "overcome." (Quoting Ward, 972 F.3d at 374.) We
are not convinced.
The government points out that in 1989, the Commission
amended the definition of "controlled substance offense," which
was previously defined as "an offense identified in 21 U.S.C.
§§ 841, 952(a), 955, 955a, 959; §§ 405B and 416 of the Controlled
Substances Act as amended in 1986, and similar offenses." (Quoting
U.S.S.G. § 4B1.2(2) (1987).) See also U.S.S.G. App. C, at 138
- 40 -(1989) (removing the reference to specific United States Code
provisions and replacing it with the "controlled substance"
language used in the version at issue here). The government then
posits that because the Commission removed the cross-reference to
the CSA in 1989 from its definition of "controlled substance
offense," the absence of a cross-reference in its current
definition of "controlled substance offense" implies that a
controlled substance is defined with reference to either state or
federal law.
The application notes predating the amendment make
clear, however, that "an offense identified in [the CSA], and
similar offenses," U.S.S.G. § 4B1.2(2) (1987), already included
both federal and state offenses. See id. cmt. n.2 ("'Controlled
substance offense' means any of the federal offenses identified in
the statutes referenced in § 4B1.2, or substantially equivalent
state offenses."); see also United States v. Giggey, 551 F.3d 27,
34 (1st Cir. 2008) ("Commentary in the Guidelines Manual that
interprets or explains a guideline is authoritative unless it
violates the Constitution or a federal statute, or is inconsistent
with, or a plainly erroneous reading of, that guideline." (citation
modified)). The amendment therefore does not address the asserted
textual ambiguity at issue.
The question remains, in other words, whether a
substance is "controlled" under the Guideline when the substance
- 41 -in question is controlled by the relevant state or only when it is
controlled by the federal government. And, in form, that question
is not materially distinct from the question that the Court
confronted in Jerome about what constituted a "felony" and to which
Jerome applied the presumption in favor of federal law supplying
the answer.
The government also points out that the absence of any
cross-reference to the provision of federal law that defines
controlled substances -- namely, the CSA -- is conspicuous because
the Commission has demonstrated the capacity to explicitly
cross-reference federal law when it so desires. The government
points out in that regard that the Commission incorporates
statutory definitions of "firearm" and "explosive material" into
§ 4B1.2(a)(2). See U.S.S.G. § 4B1.2(a)(2) (referencing 26 U.S.C.
§ 5845(a) and 18 U.S.C. § 841(c)). Additionally, the government
notes that the Commission redefined "crime of violence" to match
"nearly verbatim" the definition of "violent felony" in ACCA but
chose to not adopt ACCA's definition of "controlled substance
offense," which did explicitly reference the CSA. (First citing
18 U.S.C. § 924(e)(2)(B); and then citing id. § 924(e)(2)(A)(ii).)
See U.S.S.G. § 4B1.2(a) (defining "crime of violence").
Thus, the government reasons, because the Commission
knows how to expressly tie the term "controlled substance" to a
provision of federal law, we must infer that the Commission's
- 42 -choice to not make such a cross-reference is an indication that it
intended to refer to a substance that is controlled by either
federal or state law. The government then adds that this textual
implication is reinforced by the fact that the Guideline's plain
terms make clear that the Guideline may be triggered by a state or
federal conviction. See U.S.S.G. § 4B1.2(b) (defining "controlled
substance offense" as "an offense under federal or state law").
In other words, the government argues, by providing that a state
law conviction for a controlled substance offense can trigger the
Guideline, the Guideline must look to state law itself to define
what constitutes a "controlled substance."
The government overlooks the fact, though, that a
specific cross-reference to the federal CSA could have, through
the reference canon, tied the application of the career offender
guideline to the CSA in effect at the time of the Guideline's
enactment. See Jam, 586 U.S. at 209-10 ("[A] statute that refers
to another statute by specific title or section number in effect
cuts and pastes the referenced statute as it existed when the
referring statute was enacted, without any subsequent
amendments."). Thus, the absence of a specific cross-reference is
not a clear indication that the Commission intended to make the
application of the career offender guideline dependent on state
law, such that the Jerome presumption is overcome. And while we
agree that the word "offense" in the Guideline is plainly inclusive
- 43 -of a state law offense, given the express inclusion of "an
offense . . . under state law," U.S.S.G. § 4B1.2(b), the question
of whether a substance must be "controlled" under state or federal
law to be a "controlled substance" is not similarly plainly
resolved elsewhere in the Guideline.
So, as Congress did in Jerome, the Commission here failed
to define the relevant term -- namely, in this case, "controlled
substance." And, like in Jerome with respect to states'
definitions of "felony" for the federal statute there at issue,
the inclusion of states' definitions of "controlled substance" is
not necessary to effectuate the career offender guideline. 318
U.S. at 107 ("Finally, the inclusion of state crimes in the word
'felony' neither comports with the scheme of the Act nor is
necessary to give the Act meaning and vitality."). Nor is it
clear, given the absence of a definition of that term, that the
Commission intended for "controlled substance" to sweep up every
state's definition of the same. Accordingly, we now make clear
what Crocco suggested: "Controlled substance" is defined in
reference to federal law, exclusively, and in a way that is easily
administered and avoids the inconsistency that could follow from
- 44 -merely handing over the definition of a "controlled substance" to
each state.15
5.
In sum, we agree with Fulcar that what matters is whether
ioflupane was "controlled" by the federal government at the time
of his federal sentencing. And, because it was not, we also agree
with Fulcar that the District Court erred in applying the career
offender guideline to him based on his 2008 Massachusetts law
conviction for possession with intent to distribute "cocaine."
Even still, we are not done assessing this ground for
challenging Fulcar's sentences. The government does not argue
that, insofar as the District Court made an error in applying the
career offender guideline's enhancement in sentencing Fulcar, that
error did not affect his sentences. But, as we noted in recounting
the procedural history, the District Court made it clear that
"whether or not [it] had accepted [Fulcar's] arguments about what
the advisory guideline sentencing range should be, that is, if
15 We are reasonably confident that the foregoing weighs in
favor of reading the Guideline as referring only to substances
controlled by federal law. But even if we were left with "a
grievous ambiguity or uncertainty," Shaw v. United States, 580
U.S. 63, 71 (2016) (quoting Muscarello v. United States, 524 U.S.
125, 138-39 (1998)), the issue would call for application of the
rule of lenity, which "requires a court to resolve true statutory
uncertainty in the accused's favor," United States v. Ahlers, 305
F.3d 54, 62 (1st Cir. 2002). See also United States v. Luna-Diaz,
222 F.3d 1, 3 n.2 (1st Cir. 2000) (noting that "the rule of lenity
applies" to the interpretation of the Guidelines, by virtue of it
being similar to the interpretation of criminal statutes).
- 45 -[it] had accepted them, [it] would have still reached the same
sentence [it was] imposing [t]here, having considered all of the
factors under Title 18, United States Code, 3553(a)."
We therefore conclude that although the District Court
erred in its application of the career offender guideline, that
error was harmless. See, e.g., Marsh, 561 F.3d at 86 ("[T]he
district court stated that it would have imposed the same sentence
as a non-Guideline sentence under 18 U.S.C. § 3553(a). If we find
an alleged Guideline error would not have affected the district
court's sentence, we may affirm." (citation omitted)).
Accordingly, we see no reason to vacate the sentences based on the
District Court's application of the career offender guideline.
B.
There remains to address, then, Fulcar's challenges to
two other sentencing enhancements, which the District Court
suggested would have applied to the calculation of his Guidelines
sentencing range for his § 922(g)(1) conviction if not for the
already-applied career offender enhancement: the § 2K2.1(a)(2)
enhancement and the § 2K2.1(b)(6)(B) enhancement. Fulcar
acknowledges that the District Court did not specifically find
that these enhancements applied to Fulcar because it determined,
due to grouping, that the career offender calculation yielded a
higher sentencing range under the Guidelines and drove the range
- 46 -calculation. Fulcar nonetheless argues that to the extent that
this was a finding, it was clear error.16
We need not decide whether this finding, if it was made,
was clear error. As mentioned above, the District Court made clear
that even if it had accepted Fulcar's "arguments about what the
advisory guideline sentencing range should be," it "would have
still reached the same sentence" under 18 U.S.C. § 3553(a). And
given that two of the objections to the Guidelines calculation
that Fulcar levied were precisely to the application of
enhancements under § 2K2.1(a)(2) and § 2K2.1(b)(6)(B), it is clear
the District Court would have imposed the same sentence regardless
of its findings on these specific objections. Thus, this
challenge, too, is unavailing. See Marsh, 561 F.3d at 86.
V.
For the foregoing reasons, Fulcar's convictions and
sentences are affirmed.
The § 2K2.1(a)(2) Guideline applies where a § 922(g)(1)
16
defendant has two prior convictions "of either a crime of violence
or a controlled substance offense." Section 2K2.1(a)(2)
incorporates the definition of "controlled substance offense" from
the career offender guideline we have just analyzed. U.S.S.G.
§ 2K2.1 cmt. n.1. Thus, if not for the harmlessness of the error,
we would find that application of § 2K2.1(a)(2) to Fulcar was error
for the same reasons given above with respect to the career
offender guideline.
- 47 -