20-4162 United States v. Chaires
United States Court of Appeals For the Second Circuit
August Term 2021
Argued: December 8, 2021 Decided: December 7, 2023
No. 20-4162
UNITED STATES OF AMERICA,
Appellee,
v.
ROBERT J. CHAIRES,
Defendant-Appellant.
Appeal from the United States District Court for the Northern District of New York No. 18-cr-21-1, Frederick J. Scullin, Judge.
Before: CARNEY, SULLIVAN, and MENASHI, Circuit Judges.
Robert J. Chaires challenges the procedural and substantive reasonableness of the 120-month sentence imposed by the district court (Scullin, J.) following his plea of guilty to two counts of unlawfully distributing cocaine base in violation of 21 U.S.C. §§ 841(a)(1) and 841(b)(1)(B). On appeal, Chaires principally argues that the district court erred when it found that Chaires’s two prior state-court narcotics convictions categorically qualified as predicate offenses for the career offender enhancement under U.S.S.G. § 4B1.1. Based on this Court’s intervening decision in United States v. Minter, 80 F.4th 406 (2d Cir. 2023), it is now clear that the district court erred when it sentenced Chaires as a career offender under U.S.S.G. § 4B1.1. As the government concedes, the district court’s career offender determination was premised on Chaires’s two prior state-court convictions brought under a state provision that is categorically broader than the federal predicate definition in section 4B1.2(b). Those convictions thus cannot serve as section 4B1.1 predicate offenses and the district court therefore plainly erred when it enhanced Chaires’s Guidelines range on that basis. Accordingly, we REMAND the case to the district court for resentencing. Judge Sullivan concurs in a separate opinion.
REMANDED.
ROBERT JOSEPH BOYLE, Esq., New York, NY, for Defendant-Appellant.
CARINA H. SCHOENBERGER (Michael S. Barnett, Rajit S. Dosanjh, on the brief), Assistant United States Attorneys, for CARLA B. FREEDMAN, United States Attorney for the Northern District of New York, Syracuse, NY, for Appellee.
PER CURIAM:
Robert J. Chaires challenges the procedural and substantive reasonableness
of the 120-month sentence imposed by the district court (Scullin, J.) following his
plea of guilty to two counts of unlawfully distributing cocaine base in violation of
21 U.S.C. §§ 841(a)(1) and 841(b)(1)(B). On appeal, Chaires principally argues that
the district court erred when it found that Chaires’s two prior state-court narcotics
2 convictions categorically qualified as predicate offenses for the career offender
enhancement under U.S.S.G. § 4B1.1. Based on this Court’s intervening decision
in United States v. Minter, 80 F.4th 406 (2d Cir. 2023), it is now clear that the district
court erred when it sentenced Chaires as a career offender under U.S.S.G. § 4B1.1.
As the government concedes, the district court’s career offender determination
was premised on Chaires’s two prior state-court convictions brought under a state
provision that is categorically broader than the federal predicate definition in
section 4B1.2(b). Those convictions thus cannot serve as predicate offenses to
section 4B1.1 and the district court therefore plainly erred when it enhanced
Chaires’s Guidelines range on that basis. Accordingly, we remand the case for
resentencing.
I. BACKGROUND
As relevant here, Chaires has two prior state-court drug convictions. In
2003, he pleaded guilty to the criminal sale of a controlled substance in the third
degree under N.Y. Penal Law § 220.39(1) and was ultimately sentenced to eight
years’ incarceration. 1 In 2008, while he was still on parole for the 2003 conviction,
1Chaires was initially sentenced to four to twelve years’ incarceration but that sentence was vacated in 2012 after the state legislature reduced the statutory maximum for section 220.39(1). Chaires was then resentenced to his ultimate term of eight years’ incarceration.
3 Chaires was arrested for selling powder cocaine and ultimately pleaded guilty to
attempting to violate section 220.39(1). Though the court sentenced Chaires to four
years’ incarceration, he was given an alternative sentence in the form of a three-
month drug treatment bootcamp, which he completed in November 2008. About
a year after his release from bootcamp, however, Chaires’s parole was revoked
after a routine search uncovered marijuana and ammunition in his residence. In
lieu of a parole hold, Chaires was diverted to a drug treatment facility and then
released back into supervision in April 2010. Chaires was ultimately discharged
from parole in 2011.
Seven years later, in 2018, Chaires was again arrested for narcotics
trafficking, this time by federal agents after he sold approximately eighty grams
of crack cocaine to a confidential source. A federal grand jury later indicted
Chaires on two counts of distributing crack cocaine in violation of 21 U.S.C.
§§ 841(a) and 841 b(1)(B).
On August 31, 2020, Chaires pleaded guilty to both counts. That same day,
Chaires filed a written objection to his potential classification as a career offender
under section 4B1.1 of the United States Sentencing Guidelines, asserting without
elaboration that his 2008 conviction for attempted trafficking did not qualify as a
4 predicate “controlled substance offense” under the career offender enhancement.
Chaires mounted another objection in his December 2, 2020 sentencing
memorandum, arguing that the 2008 attempt conviction could not serve as a career
offender predicate because it was merely an inchoate offense.
The district court sentenced Chaires on December 7, 2020. During that
hearing, Chaires’s counsel again argued that Chaires’s 2008 conviction was for an
inchoate offense that could not serve as a career offender predicate. The district
court disagreed and found that Chaires qualified as a career offender based on his
2003 and 2008 convictions under section 220.39(1), which yielded an advisory
Guidelines range of 188 to 235 months’ imprisonment. Nonetheless, the district
court ultimately imposed a below-Guidelines sentence of 120 months’
imprisonment followed by four years of supervised release.
Chaires timely appealed and we heard argument on December 8, 2021. Our
decision was delayed, however, while we waited our turn in a queue of cases
involving the categorical approach to narcotics predicates under the Guidelines’
career offender enhancement. See U.S.S.G. § 4B1.1. We ultimately decided two of
those cases on grounds that go to the heart of the sentencing challenges that
Chaires now raises. The first, United States v. Gibson, 55 F.4th 153 (2d Cir. 2022),
5 adhered to on reh’g, 60 F.4th 720 (2d Cir. 2023), affirmed the district court’s finding
that N.Y.P.L § 220.39(1) is categorically broader than its federal analog and
therefore cannot trigger the career offender enhancement under section 4B1.1.
After we directed the parties to submit supplemental briefing on whether Gibson
was a precedential holding that bound us here, another panel of this Court decided
Minter, 80 F.4th at 406. At issue there was whether N.Y.P.L. § 220.39(1) – the same
provision as here – was categorically broader than the federal drug schedules.
Given that the state provision covers certain cocaine isomers that federal law does
not, we found that it was. Id. at 410, 413 (citing the federal Controlled Substances
Act (“CSA”), 21 U.S.C. § 802). As a result, we concluded that the defendant’s
convictions under section 220.39(1) could not serve as predicate offenses under the
Armed Career Criminal Act (“ACCA”), 18 U.S.C. § 924(e)(1). Minter, 80 F.4th at
407.
The parties have now filed supplemental briefs addressing the significance
of Gibson and Minter, and while they continue to dispute whether Gibson is a
precedential opinion that is binding on future panels, both agree that Chaires’s
state-law convictions are not predicate narcotics offenses to section 4B1.1 after
Minter.
6 II. STANDARD OF REVIEW
We review criminal sentences for reasonableness. United States v. Jones, 531
F.3d 163, 170 (2d Cir. 2008). As part of that review, we must “first ensure that the
district court committed no significant procedural error, such as failing to calculate
(or improperly calculating) the Guidelines range.” See Gall v. United States, 552
U.S. 38, 39 (2007). To that end, we review the district court’s Guidelines calculation
de novo, including whether the district court properly determined that the career
offender enhancement applies. See United States v. Savage, 542 F.3d 959, 964 (2d
Cir. 2008) (citing U.S.S.G. § 4B1.2).
Because the defendant here failed to preserve his sentencing challenge,
however, we will reverse only if we find plain error. Under that standard, we
consider whether “(1) there is an error; (2) the error is clear or obvious, rather than
subject to reasonable dispute; (3) the error affected the appellant’s substantial
rights; and (4) the error seriously affects the fairness, integrity or public reputation
of judicial proceedings.” United States v. Miller, 954 F.3d 551, 557–58 (2d Cir. 2020).
III. DISCUSSION
Although Chaires raises a host of challenges to his sentence on appeal, we
need only decide whether Chaires’s prior state-law convictions under N.Y.P.L
7 § 220.39(1) qualify as predicate offenses for the career offender enhancement
under section 4B1.1. On that score, we agree with the parties that neither of
Chaires’s prior state convictions is a valid predicate after Minter. Because we also
find this was plain error, we must remand for resentencing.
A. The Categorical Approach
The Sentencing Guidelines prescribe enhanced penalties for certain
defendants with significant criminal histories. In particular, section 4B1.1 – the
career offender enhancement – directs that defendants are subject to a higher
Guidelines range when they have at least two prior felony convictions for “a
controlled substance offense.” U.S.S.G. § 4B1.1. According to the Guidelines,
“[t]he term ‘controlled substance offense’ means an offense under federal or state
law, punishable by imprisonment for a term exceeding one year, 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).
In deciding whether a state conviction qualifies as a “controlled substance
offense,” courts must compare the state statute underlying that conviction to the
federal definition in section 4B1.2(b). Since 2018, we have applied the “categorical
8 approach” to that comparison, examining the elements of the defendant’s
conviction and asking whether those elements criminalize any conduct that
section 4B1.2(b) does not cover. See United States v. Townsend, 897 F.3d 66, 72 (2d
Cir. 2018).
We perform this categorical approach in two steps. See Stuckey v. United
States, 878 F.3d 62, 67 (2d Cir. 2017). First, we “identify the ‘elements of the statute
forming the basis of the defendant’s [prior state] conviction.’” Id. (quoting United
States v. Descamps, 570 U.S. 254, 257 (2013)). 2 “In doing so, we examine what is the
minimum criminal conduct necessary for conviction under that particular state
statute.” Id. (alterations and internal quotation marks omitted).
Once we have identified the elements underlying the defendant’s prior state
conviction, we “compare” those elements with the conduct that constitutes a
“controlled substance offense” under section 4B1.2(b) of the career offender
enhancement. See Townsend, 897 F.3d at 73. If the state provision “sweeps more
2This first step will often be straightforward, since the statute of conviction will list the elements of only a single crime. However, certain statutes list the elements of multiple alternative offenses in a single provision. When a statute has such a “divisible” structure, we modify the first step by “look[ing] to a limited class of documents (for example, the indictment, jury instructions, or plea agreement and colloquy) to determine what crime, with what elements, a defendant was convicted of.” Stuckey, 878 F.3d at 67. Here, we need not determine whether section 220.39(1) is divisible because the government has “conce[ded]” that it is not. Govt’ Supp. Br. at 5. We therefore assume without deciding that section 220.39(1) is indivisible and apply the traditional categorical approach.
9 broadly” – meaning it punishes some conduct that is not prohibited by federal
“controlled substance offense[s]” – then no conviction under that provision can
serve as a predicate controlled substance offense for the section 4B1.1 career
offender enhancement. See id. at 74.
This categorical comparison often turns on whether the state offense
criminalizes even a single substance that federal law does not. In Townsend, we
held that the term “controlled substance” in section 4B1.2(b) refers “exclusively to
those drugs listed under . . . the [federal] CSA.” See id. at 71. This means that,
when we apply the categorical approach to “controlled substance offense[s]” in
section 4B1.2(b), we ask whether the defendant’s prior state conviction was under
a statute that covers any substance not listed in the CSA. For instance, Townsend
itself held that a New York state conviction under N.Y.P.L. § 220.31 could not serve
as a section 4B1.1 predicate because that state provision criminalized at least one
substance – “human chorionic gonadotropin” – not covered by the CSA. See id.
Under the categorical approach, it does not matter if the defendant’s conviction
was in fact premised on a substance that was clearly prohibited by both the state
and federal narcotics laws, such as heroin or cocaine; the categorical approach
10 looks exclusively at statutory elements and does not inquire into the “particular
controlled substance” underlying the defendant’s prior state conviction. Id.
B. Chaires’s Prior Convictions Under Section 220.39(1)
At sentencing, the district court found that Chaires was a career offender
because he had two prior convictions under N.Y.P.L. § 220.39(1). In light of Minter,
neither of those convictions can serve as a career offender predicate here.
Because the parties stipulate that N.Y.P.L § 220.39(1) is not divisible, see
supra note 2, we need only compare the elements of section 220.39(1) with section
4B1.2(b) to determine if section 220.39(1) covers any conduct that is not a
“controlled substance offense.” Section 220.39(1)’s text reveals four elements: the
defendant must (1) knowingly and (2) unlawfully (3) sell (4) a ”narcotic drug” as
defined in N.Y.P.L. § 220.00(7). Cf. Townsend, 897 F.3d at 74 (identifying the
elements of the analogous offense enumerated in N.Y.P.L. § 220.31). Under our
recent holding in Minter, it is clear that section 220.39(1) sweeps more broadly than
its federal analog and cannot serve as a “controlled substance offense.” As even
the government concedes here, Minter interpreted the term “narcotic drug” in
section 220.39(1) and found that it covered several cocaine isomers not listed in the
CSA. See Minter, 80 F.4th at 410 (concluding that New York law criminalizes all
cocaine isomers while federal law exempts “optical and geometric” isomers).
11 Given that section 220.39(1) covers some conduct – the sale of these cocaine
isomers – that the CSA does not, Chaires’s prior state convictions under 220.39(1)
cannot serve as predicates to the career offender enhancement under our Circuit’s
categorical approach.
While Chaires did not preserve a Minter-style argument before the district
court, the clarity of Minter’s holding itself establishes plain error and compels us
to remand for resentencing. See Miller, 954 F.3d at 557–78 (reciting the four prongs
for plain error). First, as already established, the district court erred when it
calculated Chaires’s Guidelines range based on his (mistaken) status as a career
offender. See United States v. Wernick, 691 F.3d 108, 112 (2d Cir. 2012) (holding that
such miscalculations satisfy the “error” prong). Second, this error was also plain,
because Minter has now established as the law of the Circuit that section 220.39(1)
covers certain cocaine isomers that the federal CSA does not. See United States v.
Garcia, 587 F.3d 509, 520 (2d Cir. 2009) (holding that errors are plain when they are
“clear” at the “time of appeal,” even if not so at the time of sentencing). This error
also meets the final two prongs of the plain error analysis, since the miscalculation
of Chaires’s Guidelines range had “a potentially serious impact on the sentence
imposed.” Wernick, 691 F.3d at 117 (quoting United States v. Dorvee, 616 F.3d 174,
12 181–82 (2d Cir. 2010)) (holding that such miscalculations satisfy both the third and
fourth prongs). Indeed, without the career offender enhancement, it appears that
Chaires’s Guidelines range would have dropped from 188 to 135 months to only
60 to 71 months 3 – well below the 120-month sentence imposed by the district
court. 4
IV. CONCLUSION
For these reasons, we REMAND the case for resentencing.
3Based on the Presentence Investigation Report, to which neither party has objected, Chaires’s total offense level would have been 23 and his criminal history category would have been III. The Sentencing Guidelines table prescribed a range of 57 to 71 months while Chaires’s federal conviction carried a mandatory minimum of five years. As a result, Chaires’s Guidelines range apparently would have been 60 to 71 months. 4Of course, on remand the district court is not bound by the advisory Guidelines range and may impose whatever sentence it deems necessary to meet the sentencing objectives of 18 U.S.C. § 3553(a). See United States v. Davis, 139 S. Ct. 2319, 2336 (2019); United States v. Sindima, 488 F.3d 81, 87 (2d Cir. 2007).
13 20-4162 United States v. Chaires
RICHARD J. SULLIVAN, Circuit Judge, concurring:
I agree with the majority that, based on our Circuit’s binding precedents,
Chaires’s prior narcotics convictions cannot serve as predicates to the career
offender enhancement and that we therefore must remand for resentencing. I
write separately to question the wisdom of those precedents and explain why, in
my view, the “controlled substance offense” predicate to U.S.S.G. § 4B1.1 – the
career offender enhancement – does not call for a categorical comparison of drug
schedules.
Although the Supreme Court has held that the categorical approach applies
to “violent felony” predicates under the Armed Career Criminal Act (“ACCA”),
18 U.S.C. 924(e), it did so based on ACCA’s unique text, statutory history, and
practical implications. See Taylor v. United States, 495 U.S. 575 (1990). The Supreme
Court has never extended the categorical approach to the “controlled substance
offense” predicate of the career offender enhancement defined in section 4B1.2(b),
which shares none of ACCA’s salient features. What’s more, the plain text of
section 4B1.2(b) indicates that the Sentencing Commission prescribed a state-
dependent approach that does not turn on the content of federal drug schedules
or their exact match with a state-law analog. Indeed, six of our sister circuits have already concluded as much, holding that section 4B1.2(b) calls for a state-
dependent approach rather than a categorical one. See United States v. Jones, 81
F.4th 591, 599 n.5 (6th Cir. 2023) (noting the 6-3 circuit split over this issue, with
our Circuit in the minority). Though our Circuit rejected the state-dependent
approach in United States v. Townsend, 897 F.3d 66 (2d Cir. 2018), I continue to
believe it is the correct reading of section 4B1.2(b).
I.
In United States v. Taylor, the Supreme Court held that courts must apply the
“categorical approach” to determine whether a prior state conviction qualifies as
a “burglary” predicate under ACCA. Taylor, 495 U.S. at 602. In so holding, the
Court also considered and rejected two other tests: the factual approach and the
state-dependent approach. Under the factual approach, a court would examine
the facts underlying the defendant’s conviction and determine whether “the
defendant’s actual conduct would fit the generic definition of burglary.” Id. at 601.
So, for instance, a prior state conviction where a defendant burglarized a boat
would not count as a predicate, since the generic definition of burglary is limited
to buildings or structures. See id. at 599. Under the state-dependent approach,
meanwhile, a defendant’s prior conviction for burglary under state law would
2 always qualify as a predicate, no matter how each “state chooses to define it.” Id.
at 579 (internal quotation marks omitted). Unlike the factual approach, then, a
state conviction for burglarizing a boat would qualify, simply because that
conduct was an offense under the state’s burglary law.
In rejecting these two approaches, the Court gave three principal reasons
why ACCA’s violent felony clause called for the categorical approach. First,
ACCA’s text defined violent felony predicates based on their “element[s].” 18
U.S.C. § 924(e)(2)(B)(i) (defining a violent felony, in relevant part, as one that “has
as an element . . . the use of physical force”). The Court interpreted this as a
directive from Congress that sentencing courts must look to “the elements of the
statute of conviction, not to the facts of each defendant’s conduct.” Taylor, 495 U.S.
at 601.
Second, ACCA’s amendment and legislative history suggested that
Congress had always intended for a categorical approach to apply to violent felony
predicates. The Court pointed to various bill proposals and floor statements that
suggested that all burglaries should categorically qualify as violent felonies, even
if a particular defendant had not in fact engaged in violence when committing
their offense. Id. at 582–89. The Court also observed that ACCA was originally
3 enacted with statutory definitions of generic burglary and robbery (the original
two ACCA predicates). 1 Id. at 589–90. To the Court, this demonstrated that
Congress must have wanted a categorical standard (rather than a state-dependent
approach) where the “enhancement provision [would] be triggered by crimes
having certain specified elements, not by crimes that happened to be labeled
‘robbery’ or ‘burglary’ by the laws of the State of conviction.” Id. at 588–89.
Third, the Court observed that the categorical approach would yield fewer
“practical difficulties” than the other two options. Id. at 601. A state-dependent
approach would lead to “odd results,” the Court thought, because the same
conduct would be a predicate in one state yet not one in another that defined
burglary differently. Id. at 591. The factual approach, on the other hand, would
seemingly require the parties to relitigate anew the facts of the state conviction, an
arduous process that could even involve dueling witnesses. Id. at 601–02.
1 Burglary, for instance, was defined as “any felony consisting of entering or remaining surreptitiously within a building that is property of another with intent to engage in conduct constituting a Federal or State offense.” Taylor, 495 U.S. at 581 (quoting Armed Career Criminal Act of 1984, Pub. L. 98-473, ch. 18, 98 Stat. 2185, 18 U.S.C. § 1202(a) (Supp. III 1982) (repealed 1986)). Though Congress removed those definitions a few years later, the Court still determined that the deletion may have been “inadvertent” and that the initial inclusion signaled an overall preference for uniform definitions. Id. at 590.
4 II.
In United States v. Townsend, our Court extended Taylor’s categorical
approach to the “controlled substance offense” predicate to the career offender
enhancement. 897 F.3d at 75 (citing U.S.S.G. § 4B1.2(b)). In particular, we
instructed courts to apply section 4B1.2(b) by comparing the state drug conviction
to the federal CSA to determine whether the state offense necessarily involved a
federally controlled substance. See id. at 74.
In my view, that was wrong. The career offender enhancement lacks the
features that Taylor found critical when it prescribed the categorical approach for
ACCA’s violent felony predicates. More than that, several features of the career
offender enhancement – chiefly its plain text – point instead to a state-dependent
approach for controlled substance offenses.
A.
As always, we start with the text. In relevant part, section 4B1.2(b) defines
a “controlled substance offense” as “an offense under federal or state law . . . that
prohibits . . . distribution . . . of a controlled substance.” U.S.S.G. § 4B1.2(b). On
my read, nothing in that text points toward Taylor or its categorical approach.
Unlike ACCA’s violent felony clause, section 4B1.2(b) says nothing about
“element[s].” Cf. 18 U.S.C. § 924(e)(2)(B)(i) (defining an offense that “has as an
5 element the use, attempted use, or threatened use of physical force against the
person of another” (emphasis added)). In fact, section 4B1.2(b) stands in stark
contrast to section 4B1.2(a), in which the Commission specifically referred to
“element[s]” when defining the “crime of violence” predicate to the career
offender enhancement. § 4B1.2(a)(1) (“The term ‘crime of violence’ means any
offense under federal or state law . . . that . . . has as an element the use, attempted
use, or threatened use of physical force against the person of another.” (emphasis
added)). Obviously, the Commission knew how to define predicate offenses in a
manner that (like the statute at issue in Taylor) would trigger the categorical
approach, yet chose not to do so when defining “controlled substance offense.”
If anything, section 4B1.2(b)’s text affirmatively supports a state-dependent
approach. For starters, section 4B1.2(b) defines “controlled substance offense” in
relevant part to include “an offense under federal or state law . . . that prohibits the
manufacture, import, export, distribution, or dispensing of a controlled
substance.” Id. § 4B1.2(b) (emphasis added). By using the disjunctive “or,” the
Commission directed that “state law” offenses qualify as predicates on equal
footing with federal ones, even if “federal” law differs in its scope. Meanwhile,
the plain meaning of “controlled substance” is a “drug[] regulated by law.” United
6 States v. Lewis, 58 F.4th 764, 769 (3d Cir. 2023); see also Controlled substance, The
Random House Dictionary of the English Language (2d ed. 1987) (“any of a
category of behavior-altering or addictive drugs, such as heroin or cocaine, whose
possession and use are restricted by law”). Taking these two points together, I
think section 4B1.2(b) plainly says that state offenses for trafficking drugs can
qualify as predicates, no matter the content of federal law.
To be sure, our Circuit held otherwise in Townsend, concluding that a state
offense can be a “controlled substance offense” only if the state offense
categorically matches the federal CSA. See Townsend, 897 F.3d at 66, 68, 71. We
first reasoned, under the Jerome presumption, that federal statutes presumptively
do not rely on state law unless the legislature “plainly indicates otherwise.” Id. at
71 (citing Jerome v. United States, 318 U.S. 101, 104 (1943)). On that basis, we
concluded that section 4B1.2(b) was cross-referencing the federal CSA – and not
incorporating state law – when it employed the term “controlled substance.” 2
But like several of our sister circuits, I find it obvious that the Commission
plainly indicated “otherwise,” id., when it explicitly said that offenses under either
“federal or state law” may count as predicates under section 4B1.2. Jones, 81 F.4th
2Though we normally apply that presumption to federal statutes, Townsend found that it applied to the Guidelines, too, because they also have the force of law. See Townsend, 897 F.3d at 71.
7 at 598 (emphasis added); see also United States v. Ward, 972 F.3d 364, 374 (4th Cir.
2020) (explaining that “section 4B1.2(b) disjunctively refers us to state law in
defining the offense” so the presumption in favor of federal law “is overcome
here”). Put simply, if the Commission had wanted to limit “controlled substance
offense[s]” to those that mirror federal law, it knew full well how to do so. After
all, the Commission cross-referenced federal statutes in the clause right above
“controlled substance offense,” where section 4B1.2(a) defines its “crime of
violence” predicate based on two federal provisions. See U.S.S.G. § 4B1.2(a)(2)
(citing 26 U.S.C. § 5845(a) and 18 U.S.C. § 841(c)). This is also true of other
Guidelines provisions, which cross-reference federal statutes when prescribing
sentences for drug-trafficking offenses. See Ward, 972 F.3d at 373 (citing U.S.S.G.
§ 2D1.1, which in turn cross-references a host of federal narcotics provisions in 21
U.S.C. §§ 841 and 960).
What is more, the Commission actually deleted such a cross-reference to the
CSA that originally appeared in section 4B1.2. When the Commission first
promulgated the Guidelines, it defined “controlled substance offense” based on
federal law – that is, “an offense identified in 21 U.S.C. §§ 841, 952(a), 955, 955a,
959; §§ 405B and 416 of the Controlled Substance Act as amended in 1986, and
8 similar offenses.” U.S.S.G. § 4B1.2(2) (1987). But just two years later, the
Commission deleted those cross-references to the CSA, leaving section 4B1.2 in its
substantially current form: “an offense under a federal or state law prohibiting
the manufacture, import, export, or distribution of a controlled substance.” United
States v. Ruth, 966 F.3d 642, 651–52 (4th Cir. 2020) (quoting U.S.S.G. § 4B1.2(2)
(1989)). In sharp contrast to ACCA in Taylor, section 4B1.2(b)’s amendment history
points away from a categorical approach and toward a state-dependent one.
B.
Finally, I see no practical reasons for – and many against – extending the
Taylor categorical approach to section 4B1.2(b). Cf. Taylor, 495 U.S. at 601
(identifying several practical reasons for applying the categorical approach to
ACCA violent felonies). First, applying the categorical approach to the career
offender enhancement would likely “undermine[]” national uniformity, not
promote it. See United States v. Jones, 15 F.4th 1288, 1296 (10th Cir. 2021), cert. denied,
143 S. Ct 268 (2022). Indeed, under the categorical approach, sentencing courts
must disregard convictions from certain states while fully enforcing the same sort
of convictions from other states. See id. By contrast, a state-dependent approach
would create a more uniform rule where courts treat all state convictions for
controlled substances the same way.
9 In addition, a state-dependent approach would be easier to administer than
a categorical one. Under a state-dependent rubric, the sentencing court’s task is
fairly straightforward: examine the defendant’s prior conviction and assess
whether it was an offense under state (or federal) law that prohibits the trafficking
of a substance. This can generally be resolved with a brief look at the rap sheet
and the state statute of conviction. See, e.g., Ward, 972 F.3d at 371 (concluding that
a Virginia statute so qualified simply by looking at its text).
Things are not so simple under the categorical approach. To decide whether
a state drug offense is a categorical match with the CSA, courts must embark on a
needlessly convoluted journey. They must scour case law and court dockets to
find state court decisions and pattern jury instructions that indicate whether a
statute is divisible or indivisible. Cf. Harbin v. Sessions, 860 F.3d 58, 66–68 (2d Cir.
2017) (applying the categorical approach to assess indivisibility in an immigration
case). They must sift through decades-old state and federal drug codes to compare
the state schedule in place when the defendant was convicted with the federal
schedule at the time that the defendant committed his federal offense or was
sentenced for it. See United States v. Gibson, 55 F.4th 153, 162 (2d Cir. 2022) (holding
that the categorical approach requires comparing the state drug schedule at the
10 time of the defendant’s state conviction with the federal drug schedule at the time
of either the defendant’s federal offense or sentencing). And they must parse those
drug schedules chemical-by-chemical to determine which obscure substances they
do or do not cover. See United States v. Minter, 80 F.4th 406, 410–11 (2d Cir. 2023)
(analyzing whether New York regulates only “optical or geometric isomer[s]” of
cocaine or also “constitutional” or “positional” isomers). Perhaps not
surprisingly, even the circuits that originally agreed to apply the categorical
approach have split over how exactly to do so. See, e.g., Lewis, 58 F.4th at 771
(detailing the circuit split over the “time-of-sentencing” versus “time-of-
predicate” categorical approach); Cucalon v. Barr, 958 F.3d 245, 253 (4th Cir. 2020)
(surveying the different conclusions on whether drug statutes in various states are
divisible or indivisible).
C.
Significantly, recent Supreme Court decisions counsel by analogy against
using a categorical approach with respect to section 4B1.2(b). Though the Court
endorsed the categorical approach in Taylor, it has cautioned that the categorical
approach does not apply to every recidivism provision, especially when doing so
would lead to illogical results. In Nijhawan v. Holder, the Court addressed whether
the categorical approach applied to an immigration statute that required removal
11 of aliens who had been convicted of “an offense that . . . involves fraud or deceit
in which the loss to the victim . . . exceeds $10,000.” 557 U.S. 29, 38 (2009) (quoting
8 U.S.C. § 1101(a)(43)(M)(i)). As the Court explained, the categorical approach
would make little sense here because few federal or state offenses specifically
criminalize fraud causing loss over $10,000 as an element of the offense. See id. at
39–40. Since only a handful of prior convictions would categorically qualify as
predicates, the Court concluded that Congress did not “intend” the removal
provision “to be applied categorically.” Id. at 40.
The Court enlisted this same reasoning in United States v. Hayes, where it
held that the categorical approach did not apply to domestic-violence predicates
for 18 U.S.C. § 922(g), the felon-in-possession statute. 555 U.S. 415, 426 (2009).
That provision bars persons from possessing a firearm if they have been convicted
of a violent offense committed against specific family members, like current or
former spouses, parents, co-parents, and so on. See 18 U.S.C. § 921(a)(33)(A)(ii)
(defining the predicates to section 922(g)). As in Nijhawan, the Court found it
“highly improbable” that Congress intended to impose a categorical restriction,
since there were relatively few statutes that specifically criminalized violence
12 against those sorts of family members as an element of the offense. Hayes, 555 U.S.
at 427.
Applying this same logic to section 4B1.2(b), I see no reason to think that the
Commission intended for the categorical approach to apply to “controlled
substance offense[s],” since there are relatively few state laws that exactly mirror
the list of controlled substances identified in the CSA. Under Townsend, even the
slightest difference in chemical composition would serve to disqualify a prior state
conviction. As a result, convictions in New York for trafficking cocaine and heroin
(not to mention fentanyl and more than 100 other opioids and opiates) no longer
count as predicates, simply because New York law covers “constitutional isomers”
of cocaine that are not listed in the CSA. See Minter, 80 F.4th at 410–11 (citing N.Y.
Pub. Health L. § 3306 and N.Y.P.L. § 220.39(1), which in tandem treat both heroin
and cocaine as “narcotic drug[s]”). Similarly, a methamphetamine distribution
conviction in California would not be considered a predicate for the career
offender enhancement merely because California’s definition of
methamphetamine includes “optical and geometric isomers of
methamphetamine” that are not specifically mentioned in the CSA. See Lorenzo v.
Whitaker, 752 F. App’x 482, 485 (9th Cir. 2019). The categorical approach likewise
13 disqualifies marijuana convictions in Arizona or Massachusetts that occurred
before Congress decriminalized hemp in 2018, since that descheduling narrowed
the federal definition of marijuana and rendered the CSA narrower than its state
counterparts. See United States v. Bautista, 989 F.3d 698, 702–04 (9th Cir. 2021)
(Arizona marijuana convictions); United States v. Abdulaziz, 998 F.3d 519, 531 (1st
Cir. 2021) (Massachusetts marijuana convictions).
Perhaps more troubling, now that Congress has descheduled hemp, it could
be argued that no federal marijuana conviction from before 2018 can ever serve as
a career offender predicate under the categorical approach. As discussed above,
section 4B1.2(b) also includes federal offenses as predicates, so long as they
prohibit a “controlled substance” (among other things). § 4B1.2(b). But when
Congress removed hemp from the CSA in 2018, the CSA became “categorically
broader” than its pre-2018 iteration. See United States v. Batiz-Torres, 562 F. Supp.
3d 28, 33 (D. Ariz. 2021). Because we look to the current CSA when performing
the categorical approach, 3 a rigid application of the categorical approach would
mean that no pre-2018 federal conviction for trafficking marijuana would count as
a “controlled substance offense” predicate for a federal defendant sentenced
3The First and Ninth Circuits also apply this so-called “time-of-sentencing” categorical approach that compares the statute of conviction to the current CSA. See Lewis, 58 F.4th at 764.
14 today. It would not matter that the defendant was in fact convicted for trafficking
marijuana as opposed to hemp; so long as this prior conviction was under a drug
schedule (the pre-2018 CSA) that included a substance (hemp) that the current
CSA does not, the prior conviction would not meet the requirements of the
categorical approach. Indeed, a district court (from another circuit) has already
concluded that a defendant was not a career offender simply because Congress
decided to remove hemp from the federal schedules. See id. at 33. 4
Candidly, I cannot believe that the Commission intended for section
4B1.2(b) to reach such illogical results. Given section 4B1.2(b)’s plain text and
amendment history, the only plausible reading of the provision is that it calls for
a state-dependent approach that does not rely on what substances are (or were)
federally controlled.
III.
Even though the career offender guideline affects hundreds if not thousands
4 That holding assumes that CSA provisions like 21 U.S.C. § 841 are divisible by drug type and that the modified categorical approach applies. See United States v. Davis, No. 19-cr-40006, 2020 WL 998877, at *5 (S.D. Ill. Mar. 2, 2020) (finding the CSA divisible). But even that is still an open question, as the circuits have apparently not yet weighed in on the subject. See id. (citing no circuit precedent). Remarkably, if the CSA is found to be indivisible, then the categorical approach would lead to even more illogical results: the 2018 hemp descheduling would mean that the current CSA is categorically broader than the pre-2018 iteration and that no pre-2018 federal CSA conviction of any kind could ever serve as a “controlled substance offense” predicate.
15 of criminal defendants each year, the Supreme Court has exhibited little interest
in resolving the circuit split over the categorical approach. Just last year, the
Supreme Court denied certiorari in a case that sought to resolve the split. See
Guerrant v. United States, 142 S. Ct. 640 (2022). In a statement respecting that denial
of certiorari, Justice Sotomayor acknowledged that the issue had divided the courts
of appeal but lamented that “[i]t is the responsibility of the Sentencing
Commission,” not the Court, to clarify the correct approach to section 4B1.2(b). Id.
at 640–41 (Sotomayor, J., joined by Barrett, J.).
Despite some early signs of movement, the Commission has not yet
answered Justice Sotomayor’s call to action. In February 2023, the Commission
proposed two options that would resolve the circuit split over the career offender
enhancement: one that would prescribe a categorical approach, and another that
would direct a state-dependent inquiry. See U.S. Sent’g Comm’n, Proposed
Amendments to the Sentencing Guidelines 68–69 (Feb. 2, 2023),
https://www.ussc.gov/sites/default/files/pdf/amendment-process/reader-
friendly-amendments/20230201_RF-proposed.pdf [https://perma.cc/7N25-BG9P].
Regrettably, the Commission did not follow through with either proposal. In a
public meeting in April 2023, the Chair of the Sentencing Commission, Judge
16 Carlton W. Reeves, announced that the Commission was not prepared to adopt
either approach and would instead “further debate the issue over the next year.”
U.S. Sent’g Comm’n, Public Meeting 24 (Apr. 5, 2023) (statement of Hon. Carlton
W. Reeves, Chairman, U.S. Sent’g Comm’n),
https://www.ussc.gov/sites/default/files/pdf/amendment-process/public-
hearings-and-meetings/20230405/20230405_transcript.pdf
[https://perma.cc/4K7T-WBZS]. In the meantime, district courts – and criminal
defendants – must proceed as best they can under a confusing and contradictory
patchwork of authorities across the circuits.
* * *
Given the Commission’s indecision and the Supreme Court’s reluctance, I
think it imperative that the courts of appeal converge on the best reading of the
career offender enhancement. To my mind, there can be little doubt which of the
two options is that best reading. The state-dependent approach is firmly grounded
in section 4B1.2(b)’s text and will permit a relatively straightforward inquiry. The
categorical approach lacks any foothold in that text, has proven to be hopelessly
difficult to administer, and illogically disqualifies untold numbers of state and
federal narcotics convictions from serving as predicate offenses – even though
17 those convictions were in fact premised on a federally controlled substance. For
these reasons, I continue to believe that section 4B1.2(b) calls for a state-dependent
approach to controlled substance offenses, as six of our sister circuits have already
held. See Jones, 81 F.4th at 599 n.5. I therefore urge the Second Circuit to correct
this error through an en banc or mini en banc proceeding that would overrule our
currently binding precedent in Townsend and bring us in line with the majority of
circuits to have addressed this issue.