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

(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,

(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

(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,

(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

(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

(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,

(2d Cir. 2022),

5 adhered to on reh’g,

(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,

. 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”),

). 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”),

(e)(1). Minter,

.

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,

(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,

(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,

(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,

, 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,

(2d

Cir. 2018).

We perform this categorical approach in two steps. See Stuckey v. United

States,

(2d Cir. 2017). First, we “identify the ‘elements of the statute

forming the basis of the defendant’s [prior state] conviction.’”

(quoting United

States v. Descamps,

(2013)). 2 “In doing so, we examine what is the

minimum criminal conduct necessary for conviction under that particular state

statute.”

(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,

. 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,

. 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

.

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

. 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,

(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,

(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,

(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,

(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,

(quoting United States v. Dorvee,

,

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

(a). See United States v. Davis,

(2019); United States v. Sindima,

(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,

(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,

, 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,

(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,

. 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.”

.

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

. 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.”

(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].”

(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,

.

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.

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

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.”

at 588–89.

Third, the Court observed that the categorical approach would yield fewer

“practical difficulties” than the other two options.

. 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.

. 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.

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,

(quoting Armed Career Criminal Act of 1984,

ch. 18,

,

(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.

.

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.

(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.

(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,

(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,

. We

first reasoned, under the Jerome presumption, that federal statutes presumptively

do not rely on state law unless the legislature “plainly indicates otherwise.”

at

71 (citing Jerome v. United States,

(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,”

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,

.

7 at 598 (emphasis added); see also United States v. Ward,

(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

(a) and

(c)). This is also true of other

Guidelines provisions, which cross-reference federal statutes when prescribing

sentences for drug-trafficking offenses. See Ward,

(citing U.S.S.G.

§ 2D1.1, which in turn cross-references a host of federal narcotics provisions in

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

, 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,

, 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,

(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,

, 1296 (10th Cir. 2021), cert. denied,

(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

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,

(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,

, 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,

(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,

, 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,

(detailing the circuit split over the “time-of-sentencing” versus “time-of-

predicate” categorical approach); Cucalon v. Barr,

(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.”

(2009) (quoting

(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

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.”

.

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

(g), the felon-in-possession statute.

(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

(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,

.

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

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,

, 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,

, 702–04 (9th Cir. 2021)

(Arizona marijuana convictions); United States v. Abdulaziz,

(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,

, 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,

.

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

are divisible by drug type and that the modified categorical approach applies. See United States v. Davis, No. 19-cr-40006,

, 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

(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,

(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).

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,

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.

18