2 0-3049

U SA v. Gibson

1 U NITED STATES COURT OF APPEALS 2 FOR THE SECOND CIRCUIT 3 - - - - - - 4 August Term, 2021 5 ( Argued: November 23, 2021 Decided: December 6, 2022) 6 Docket No. 20-3049 7

_ ________________________________________________________ 8 U NITED STATES OF AMERICA, 9 Appellant, 10 - v. - 11 V INCENT GIBSON, 12 Defendant-Appellee

. 13

_

________________________________________________________ 14 B efore: KEARSE, LOHIER, and LEE, Circuit Judges

.1 Appeal by the United States from so much of a judgment entered in the 2 United States District Court for the Western District of New York, Lawrence J. 3 V ilardo, Judge, as sentenced defendant Vincent Gibson to 60 months' imprisonment 4 following his plea o f guilty to five counts o f ba nk robbery in violation of 18 U.S.C. 5 § 2 113(a), five counts of entering the b anks with intent t o commit larceny in violation 6 o f 18 U.S.C. § 2113(a), one c ount of ba nk la rc eny in violation of 18 U.S.C. § 2113(b), 7 and one count of interstate communication of a threat to injure in violation of 18 8 U .S.C. § 875(c). The d istrict court declined to sentence Gibson as a c a reer offender 9 under Sentencing Guidelines § 4B1.1 to a recommended imprisonment range of 151 10 t o 188 months, ruling tha t a predicate advanced by the government for the 11 enhancement--Gibson's 2002 conviction o f third-degree a ttempted criminal sale of a 12 c ontrolled substance under New York Penal Law § § 220.39(1) and 110--was n o t a 13 proper predicate because New York's controlled substanc es s chedule included 14 na loxegol, which was r e moved from the federal c ontrolled substances schedules 15 promulgated under the Controlled Substances A c t, 21 U.S.C. §§ 8 01-971, in 2015. The 16 c ourt ruled that as the New York schedule was broader than the current federal 17 schedules-- i.e. , those r e flecting federal criminal law as i t stood at the time of Gibson's 18 sentencing in the present case--Gibson's conviction under §§ 220.39(1) and 110 is not

21 a "controlled substa n c e o ffense" w ithin the meaning o f § 4 B1.1. On appeal, the 2 g overnment, which b ypassed its opportunities in the district court to a rgue that the 3 New York schedule was not broader than the current federal schedules, contends that 4 the district court misinterpreted the Guidelines by failing to compare the New York 5 schedule to the federal schedules as they existed a t the time of Gibson's state-law 6 c onviction in 2002. Finding no merit in that c o ntention, we affirm. While th ere is 7 much to be said for loo k i n g to fed era l c riminal law as it stood a t the time the 8 d efendant engaged in the conduct that constitutes his present offense, rather than at 9 the time of sentencing for his present offense, we need not decide between the two in 10 this case because either leads to affirmance. Federal criminal law--both at the time o f 11 this conduct and at the time o f sentencing for i t--was narrower than the state law that 12 g overned Gibson's 2002 conviction. 13 Affirmed. 14 KATHERINE A. GREGO RY, Assistant United States 15 Attorney, Buffalo, New York (James P. Kennedy, Jr., 16 United States Attorney for the Western District o f 17 New York, B uffalo, New Y ork, on the brief), for 18 Appellant

. 19 M A RIA NNE M A RIA NO, F e d e r a l Pub l i c D e fend e r, B u ffa l o, 20 New York, for Defendant-Appellee

.

31 KEARSE, Circuit Judge : 2 The United States appeals from so much of a judgment of the United 3 S tates District Court for the Western District of New Y ork, Lawrence J. Vilardo, Judge, 4 a s sentenced defendant V incent Gibson to 60 months' imprisonment following his 5 plea of guilty to 11 crimes committed in 2017, to wit, five counts of bank robbery in 6 v iolation of 18 U.S.C. § 2113(a), five counts of entering the banks w i th intent t o 7 c ommit larceny in violation of 18 U.S.C. § 2113(a), and one count of bank larceny in 8 v iolation of 1 8 U.S.C. § 2113(b); and one count of interstate communication of a threat 9 t o injure in violation of 18 U.S.C. § 875(c) in 2018. The government had urged the 10 c ourt to sentence Gibson as a career offender under § 4B1.1 of the advisory Sentencing 11 Gu i d e l ine s ( " Gu i d e l ine s" ) , w i thin the r e c o mmen d e d i mpri sonment r ange o f 1 5 1 t o 1 8 8 12 months. The court rej ected that request, ruling that one of the predicates advanced 13 b y the government for s uc h an enhancement--Gibson's 2002 conviction of third14 d egree attempted criminal sale of a c ontrolled substance under New York Penal Law 15 § § 220.39(1) and 110--is no t a proper predicate because New Y ork's controlled 16 substances schedule included naloxegol, which had been removed from the federal 17 c ontrolled substances schedules, promulgated under the Controlled Substances Act 18 ( "CSA"), 21 U.S.C. §§ 8 01-971, in 2015. The court ruled that "controlled substances"

41 in § 4 B1.1 refers e xclusively to substances controlled under the C SA, and that as the 2 New York schedule was broader than the schedules cu r r ently promulgated under the 3 C SA-- i.e. , those reflecting fed era l c riminal law as it stood at the time of Gibson's 4 sentencing in the present case--Gibson's conviction under §§ 220.39(1) and 110 is not 5 a c o n tro l l ed substance o ffense within the meaning o f § 4 B1.1. On appeal, the 6 g overnment, which bypassed its opportunities in the district c o urt to argue that New 7 Y ork l a w was not broader than the current federal l aw, contends that the d istrict court 8 misin terp reted the Guidelines by failing to compare the New Y ork controlled 9 substances schedule to the federal schedules as they existed at th e ti m e o f Gibson's 10 state-law conviction in 2 002. Finding no merit in that contention, we affirm. While 11 there is much to b e said for looking to federal criminal l aw as it stood at the time the 12 d efendant engaged in the conduct that constitutes his present offense, rather than at 13 the time of sentencing for his present offense, we need not decide between the two in 14 this case because either leads to affirmance. Federal criminal law--both at the time o f 15 this conduct and a t the time of sentencing for it--was narrower than the state law that 16 g overned Gibson's 2002 conviction.

51 I. BACKGROUND

2 The fa c tu a l b a ck g r o und i s no t in d i spu te . A s indicated above, Gibson ha s 3 b e en c o nvicted in the present case, pursuant to his plea of guilty, of c ommitting, inter 4 a lia, several felony crimes of violence in 2017, see, e.g. , United States v. Moore, 916 F.3d 5 2 31, 237 (2d Cir. 2019) (bank robbery " by force and violence, or by i ntimidation," 6 18 U .S.C. § 2113(a), i s a felony crime of violence). Gibson's past criminal rec o rd 7 includes his 2002 felony conviction of third-degree attempted c riminal sale of a 8 c ontrolled substance in violation of New York Penal Law §§ 220.39(1) (third-degree 9 sale) and 110 (attempt) (collectively "N.Y. §§ 2 2 0

. 3 9 ( 1 ) and 110"), and a 2004 felony 10 c onviction of first-degree attempted robbery in v i olation of New York Penal Law 11 § § 160.15(2) and 110.

12 A

. The Dispute O ver the Controlled S ubstance Predicate for Career-Offender Enhancement 13 To the extent relevant here, Guidelines § 4B1.1 provides that a defendant 14 whose current offense is a crime of violence, committed when he was over 18 years 15 o f age, "is a career offender if

. . . [he] has at least two prior felony convictions of either 16 a crime of v iolence or a controlled substance offense." Guidelines § 4B1.1(a). Those

61 " two" predicate convictions can consist either of convictions in the same category or 2 o f "one felony co nv i c ti o n of a crime of violence and one felony conviction o f a 3 c ontrolled substance offense. " Id

. § 4B1.2(c). As defined in pertinent part b y the 4 Guidelines, 5 [t]he term "controlled substance offense" means an offense under 6 federal or state law, punishable by i m p risonment for a term 7 exceeding one year, that prohibits the

. . . dispensing of a 8 controlled substance, 9 Guidelines § 4B1.2(b), or an attemp t to c ommit such an offense, see id

. Application 10 Note 1. 11 Under New York l aw, "[a] person i s guilty of criminal sale of a controlled 12 substance in the third degree when he knowingly and unlawfully sells

. . . a narcotic 13 d rug," N.Y. Penal Law § 220.39(1) (McKinney 2002)--or o f an attempt to do so, see id

. 14 § 1 10. The term "narcotic d rug" i s d efi n ed to include " any controlled substance"-- 15 o ther than methadone--"listed in schedul e . . . II(b)" of § 3306 of New York's Public 16 Health Law. N.Y. P enal L a w § 2 2 0

. 0 0(7) (McKinney 2002). As relevant here, that 17 schedule I I(b) l is t of controlled substances includes--as it apparently did in 2002-- 18 " [o]pium and opiate, and any s alt, compound, derivative, or preparation of opium or 19 opiate ." N.Y. Pub. Health Law § 3306 Schedule II(b)(1) (McKinney 2002) ("New York 20 schedule II(b)(1)") (emphases added). Naloxegol is an opium alkaloid derivative. See 71 generally Schedules of Controlled Substances: Removal of Naloxegol F rom Control, 2 80 F ed

. Reg. 3 468, 3468 (Jan. 23, 2015) ("Naloxegol Delisting Rule") ("Prior to th e 3 e ffective date o f this rule, naloxegol was a schedule II controlled substance because 4 i tcan be derived from opium alkaloids."). 5 The government, in anticipation of Gibson's plea of guilty in the present 6 c ase (without a plea agreement), submitted to the co urt a Ca lculation of Maximum 7 S entence and Sentencing Guideline Range. It contended that Gibson's record o f 8 c onviction s subjected him to the Guidelines § 4B1.1 career-offender enhancement. 9 The application of that enhancement increases a defendant's Guidelines offense level 10 and criminal history category a nd would have resulted in a recommended 11 i mprisonment range fo r Gibson of 151 to 188 months. 12 G ibs o n, in r e sponse, filed a motion asking the court not to apply th e 13 c areer-offender enhancement, contending that the necessary predicates w e r e l a cking . 14 While noting that New York attempted robbery had been held by this Court to be a 15 c rime o f violence, he argued that his 2 002 controlled substance conviction under N.Y. 16 § § 220.39(1) and 1 10 was not a proper predic ate bec a us e naloxegol, a narcotic drug 17 c riminalized b y § 220.39(1) and New York schedule II(b)(1), has been excluded from 18 federally controlled substances since 2015. ( See Gibson Memorandum o f Law dated

81 October 31, 2019 ("October Mem."), at 2-5.) Gibson pointed out that in United States 2 v . T

ownsend, 897 F.3d 66 (2d Cir. 2018) (" T o wnsend "), this Court held that "the term 3 ' controlled substance' in § 4B1.2(b) refers exclusively to substances scheduled under 4 the [CSA]"; that New York Penal L aw § 220.31 (fifth-degree criminal sale of a 5 c o ntr o l l e d sub s t an c e ) en c o m pa sse d Hu man Cho r i o ni c Gona d o tr o pin ( " HC G" ) , a d ru g 6 th a t w a s not included in the federal schedules; that § 220.31 was therefore bro a d er 7 th a n federal law; and that a conviction under § 220.31 was thus not a "c o n tro l l ed 8 substance" offense with i n th e m ea ning of § 4B1.1. (Gibson October M em. at 2, 4 9 ( citing Townsend, 8 9 7 F

. 3d a t 75).) Gibson argued that the r easoning of Townsend 10 a pplied equally t o his conviction under N.Y. §§ 220.39(1) and 110. He contended that 11 th e d is trict court should "look to the Guidelines and the state-of-the-law as it exists 12

. . . . 'on the date the defendant is sentenced'" to determine what § 4B1.1's reference t o 13 a controlled substance offense m eans w ith respect to the defendant to be federally 14 sentenced ( id

. at 5 (quoting 18 U.S.C. § 3 553(a)(4)(A)(ii)); and that the court should 15 c onclude that a c onviction under N.Y. §§ 2 2 0

. 39(1) and 110 is not a controlled 16 substance conviction within the meaning of § 4B1.1 because of New York schedule 17 II(b)(1)'s criminalization of naloxegol, which has not been a federally controlled

91 substance since 2015. Gibson argued that with o nly one possible predicate conviction 2 r emaining--the 2004 attempted robbery conviction--§ 4B1.1 was not applicable. 3 The g o vernment, while not d isputing Gibson's contention that N.Y. 4 § § 220.3 9 (1) and 110 included naloxegol and thus criminalized a broader range o f 5 c onduct than do the current C SA s chedules, argued that the district court should 6 r eject Gibson's advocated "time-of-sentencing" rule for comparing a state law to its 7 generic federal counterpart. (Government's Response in Opposition to Defendant's 8 M e morandum of L aw, dated December 2, 2019 ("Government's December 2 Mem."), 9 a t 4.) The government stated that " [i]n T ownsend, the Court specifically compared the 10 state and federal c ontrolled substa n c e schedules at the time of T ownsend's conviction , 11 not the schedules at the time of his senten c ing. 897 F.3d at 74." (Government's 12 D ecember 2 Mem

. a t 5 (em p hasis in M em.).) It also contended that this Court had 13 u sed that same r e trospective focus in Doe v. Sessions , 886 F.3d 203, 208 (2d Cir. 2018), 14 a lbeit with respect to an imm igration r emoval proceeding. The government 15 c ontended that the district court should l o o k to th e contents of the CSA schedules 16 o nly a s of the time of Gibson's 2002 conviction un d er § § 2 2 0

. 39(1) and 110; and as 17 naloxegol had been a federally proh ibi ted controlled substance at that time ( see 18 Government's December 2 Mem. at 5 (" N ew Y o rk schedule of substances in 2002

101 c orrelates with the CSA schedules in place in 2002")), the court should c onclude that 2 th a t conviction was a proper predicate for the career-offender enhancement ( s ee i d

. 3 a t 5-6).

4 B

. The Decisions of the District Court 5 After hearing o ral argument on Gibson's motion to preclude application 6 of § 4B1.1, the district court stated that it would "apply[] the current [CSA] law." 7 (Mo tion Hearing Transcript January 31, 2020 ("H.Tr."), at 9.) And a s the 2020 C SA 8 schedules did not make naloxegol a controlled subs tance, the New York schedules 9 including that substance w ere bro a der than the current federal law. The court 10 c oncluded that, under Townsend, Gibson's 2002 state-law c ontrolled substance 11 c onviction was not a p e rmi ssib l e pr e d i c a te for a § 4B1.1 career-offender enhancement. 12 In the w ake of the court's rul i n g th a t i t would not a pply the § 4B1.1 13 c areer-offender enhancement, the P r obation Office calc ulated that Gibson's total 14 o ffense l e vel and his criminal history without that enhancement would result in a 15 r ecommended imprisonment range of 92 to 115 months. Gibson thereafter sought a 16 b e low-Guidelines sentence of 60 months' imprisonment. The government, citing the 17 need for d eterrence, the nature of Gibson's c rimes, and the need to protect the public

111 from his o ffenses, argued for an above-Guidelines sentence of 1 51 to 188 months ( i.e. , 2 the same range that would have been applicable und er th e career-offender 3 enhancement). 4 At Gibson's sentencing hearing, the district court reiterated tha t i t was 5 r ejecting the c areer-offender enhancement. ( S ee Sentencing Tra n sc ript at 9.) It also 6 co n c l u ded that lenient sentencing was warranted. The court found, inter alia, th a t 7 Gibson's robberies and a ttempted robbery, in which he had given demanding notes 8 t o the bank tellers, involved no violence, no intended violence, nor e ven any thought 9 o f violence, as evidenced by the fact that when one teller simply refused to hand him 10 any money, he promptly left the bank. ( See id

. a t 30.) It a lso found that Gibson's only 11 two prior offenses h a d been committed nearly two decades earlier; that his current 12 o ffenses--confined to the length of a single month--had been "a discrete thing" when 13 he was "trying to get money to feed [his] family"; and that the current r obberies had 14 " ended when [he] had enough money to feed [ his] family, evidently, and [he] didn't 15 c ontinue with any c ri m i n a l conduct at all in that intervening year before" he was 16 a rrested. ( Id

. a t 3 0- 3 2.) Having considered the sentencing factors under 18 U.S.C. 17 § 3 553(a), the court sentenced Gibson to a below-Guidelines prison term of 60 months 18 for each of the 12 counts, all to be served concurrently.

121 The government timely appealed. It challenges o nly the district court's 2 r efusal to sentence Gibson a s a c areer offender; i t does not challenge any of the court's 3 factual findings or contest the court's decision to impose a below-Guidelines sentence 4 i f career-offender status was inapplicable.

5 II. DISCUSSION

6 We begin by noting that this appeal presents fewer issues th a n m i ght 7 have b een raised with respect to the government's proffered predicates for the career8 o ffender enhancement. First, Gibson did not challenge the use o f his attempted first9 d egree r obbery conviction a s a predicate by raising ( as he might hav e f o r i s s ue10 preservation purposes) the issue--then-percolating through the courts--of whether a 11 r obbery attempt can categorically be a "crime o f violence," see generally United States 12 v . Taylor, 142 S. Ct. 2015 ( 2 0 2 2 ) (holding that Hobbs Act attempted robbery is not a 13 c rime of violence within the meaning of 18 U.S.C. § 924(c)(3)(A)). 14 Second, in response to Gibson's contention that his controlled substance 15 c onviction could not serve as a predicate because New York schedule II(b)(1) 16 c riminalized more substances tha n a re currently criminalized by the federal

131 schedules, the government d id not argue that the New York law was not broader than 2 the current federal schedules. 3 The gov ern m en t's appeal presents a dispute over what v ersion of the 4 C SA schedules i s to b e compared against state law in c onnection with a p ro p o sed 5 c areer-offender enhancement. The government advocates use of the version in effect 6 a t the time of Gibson's state-law c ontrolled substance c onviction; Gibson argues that 7 the a ppropriate version is the one in effect at the time of sentencing in the present 8 c ase. As between these two possibilities we think Gibson's view, adopted b y the 9 d istrict court, is the more appropriate--although, as d iscussed hereafter, even the 10 v ersion in effect at the time of sentencing may not be the most appropriate.

11 A

. The Lack of Dispute as to the Current Existence of a Disparity 12 The government argued that the district court should ignore the current 13 federal schedules and look o nly to the CSA schedules as they existed a t the time o f 14 Gibson's state-law controlled substance conviction in 2002, when, the g o v ernment 15 a rgues, the state and federal schedules were the same. That timing argument was the 16 g overnment's sole position when Gibson fi rst argued that the career-offender 17 enhancement could not be applied because the relevant New York schedules

141 c riminalized more conduct than the current federal schedules; and the government 2 d id not alter its position when Gibson, in reply, pointed out that 3 [t] he g o v e rnment d o e s not seriously dispute the principal premise 4 of Mr. Gibson's argument: That New York's definition o f ' narcotic 5 drug' encompasses substances not currently scheduled under 6 federal law 7 ( Gibson Reply Memorandum dated December 9, 2019, at 1). 8 At oral a rgument of Gibson's motion to preclude applic a ti o n of the 9 c areer-offender enhancement, the distri c t c o urt began by noting that in order t o 10 d etermine the eligibil i ty of a prior state conviction to serve as a federal sentencing 11 enhancement predicate the court was required to compare the state a n d federal 12 statutes using the "categorical approach": 13 THE COURT:

. . . . [Y]ou hav e to apply the categorical 14 approach that y ou look a t the statutes. And if the s ta te statute 15 under which the defen da nt was convicted criminalizes the 16 possession of a certain subs tan ce that is not criminalized under 17 the federal statute, then the state statute doesn't [ap]ply, ri gh t? 18 Got that? 19 MR. MO LISANI [Assistant United States Attorney]: 20 Correct. 21 ( H.Tr. 2.) The government thus agreed that the categorical approach was required; 22 and it did not attempt to alter the court's explicitly stated understanding that in fact

151 " we've got a d rug here that's criminalized under the state s ta tute, but it's not under 2

. . . . the federal schedule." ( Id . at 2-3.) 3 The go vernment's position was strictly that New York law should be 4 co m p a red only a gainst the earlier version of the federal schedules. It stated th a t 5 "s o meth ing [wa]s removed from th[e federal] schedule well after the time that 6 [G ibson] was convicted of th[e state] offense," but Gibson "was convicted at a ti m e 7 where [ sic ] the schedules were exactly the same." (H.Tr. 3.) 8 The district court, having noted at the outset the undisputed need for a 9 c ategorical analysis as to whether the New York s ched ules were broader than the 10 current federal schedules, having heard Gibson's a rgument for the affirmative, and 11 having received no contrary argument from the government as to the divergence, 12 r esolved the issue. The categorical approach focuses on the generic nature of the 13 federal offense and "not [on] the facts underlying the c a se"; the court must presume 14 that the defendant's c onvicti o n " 'rested upon [ nothing] more than the least o f th[e] 15 a cts' criminalized [under state law], and then determine whether even those acts are 16 encompassed by the generic federal offense." Moncrieffe v. Holder , 569 U.S. 184, 190-91 17 ( 2013) (quoting Johnson v. Uni t e d States , 5 59 U.S. 133, 137 ( 2010)). The court here, 18 w ithout any indication that it r esorted to consideration of the facts, expressly

161 " agree[d] with" Gibson's contention that "[§] 220.39 under the New York State statute 2 i s broader than the [ current] federal sta tute." (H.Tr. 9.) Any suggestion by the 3 g overnment that the district court did not use the categorical a pproach in addressing 4 the matter of whether there w as a divergence between state law and current federal 5 l a w is belied by the record. 6 The g overnment admits that in the district court it "focused only o n 7 timing, and not whether the removal of naloxegol rendered the New York drug 8 schedule categorically broader than the C ontrolled Substances A ct." (Government's 9 r eply brief on appeal at 12.) But i f, in also stating th a t " [ t] h e g overnment does not 10 c oncede that the schedules diverged" ( id

. a t 1 1 (emphasis in o riginal)) and that it did 11 not " expressly [ so] conced[e]" in the district court ( id

. (emphasis added ) ) , the 12 g overn m en t s eeks to suggest that the existence o f disparate schedules is an 13 unresolved issue that w ould be an impediment to affirmance, i t is mistaken. While 14 the government claims that " the only issue the parties litigated was whether the district 15 c ourt should have exa m i n ed Gibson's prior conviction in light of the federal drug 16 schedule in effect at that time, or using the version in effect more than a decade later" 17 ( id

. a t 12 (emphasis a dded)), the federal courts do not engage in piecemeal 18 a djudication leading to a parade of final judgments in the same case. Th e d istrict

171 c ourt, in light of the issues presented and th e a rgum en ts made by the parties--or in 2 this c ase, forgone or unrefuted by the parties--resolved the entire case and entered 3 final judgment. The issue ra i sed by Gibson's central c o ntention--that the state and 4 federal schedules d iverged--did not r emain unresolved by the government's refusal 5 t o address it. 6 The g overnment is c orrect that it " is c onstrained from arguing on appeal 7 tha t th e d rug schedules are comparable even a fter the 2015 amendment removing 8 naloxegol," having made no such argument in the district court. ( Government's reply 9 b r i e f o n appeal a t 12; s ee also Government's main brief o n appeal at 1 1 ("That the drug 10 s chedules diverged 13 years after Gibson's offense has no b earing on whether the crime for 11 which he was actually convicted was a controlled substance offense." (emphasis 12 a dded)).) We turn to its preserved contention that the district court should consider 13 federal law o nly as it existed at the time of a defendant's conviction under state law.

14 B

. The Government's Time-of-Prior-Conviction Contention 15 In arguing that the district court, in determining the a ppl i c abi lity o f 16 § 4B1.1 for enhancement of Gibson's senten c e f o r his current federal offense, was 17 r equired to c ompare New York's schedule II(b)(1) a gainst the CSA schedules as they

181 stood at the time of his 2002 New Y o rk controlled substance conviction, rather than 2 a t the time of his sentencing for his present federal offens es , th e g overnment 3 principally relies on McNeill v. United States , 563 U.S. 816 ( 20 1 1 ) , which involved a 4 change of state law, not federal law, and on Doe v. Sessions , 886 F.3d 203 ( 2d Cir. 2018) 5 ( " Doe "), which involved immigration, not sentencing. It also proffers its own 6 interpretation of our decision in Townsend

. Reviewing the district court's Guidelines 7 interpretations and l egal rulings de novo, see, e.g. , United States v. Flores , 945 F.3d 687, 8 72 3 (2 d C ir. 2019), cert. denied, 141 S. Ct. 375 ( 2020), we reject the government's 9 c ontentions.

10 1

. The Supreme Court's Decision in McNeill 11 In support o f i ts contention that the district court in interpreting 12 " controlled substance offense" in § 4B1.1 was required to look to the CSA schedules 13 o nly as they stood at the time of Gibson's 2002 controlled substance conviction under 14 New York law, the government relies heavily o n th e Sup reme Court's decision in 15 M cNeill, 563 U.S. 816, which considered a sentencing enhancement under the Armed 16 C areer Criminal Act ( " ACCA"), 18 U.S.C. § 9 2 4(e). Under ACCA, a person who is 17 b e ing sentenced for being a felon in unlawful possession of a firearm in violation o f

191 1 8 U.S.C. § 922(g), and who "has three previous convictions

. . . for

. . . a serious drug 2 o ffense,

. . . committed on occasions d i fferent from one another," is subject to a 3 minimum o f 15 years' imprisonment. Id

. § 924(e)(1). In McNeill, the relevant ACCA 4 d efinition of a "serious drug offense" w as "an offense under State l aw, involving

. . . 5 a controlled substance

. . . for which a maximum term o f imprisonment of ten years 6 o r more is prescribed b y law." Id

. § 9 24(e)(2)(A)(ii). M cNeill had "six state drug7 trafficking convictions" under North Carolina law for crimes "committed

. . . between 8 1 991 and 1994, each carr[ying] a 1 0-year maximum sentence, and McNeill in fact 9 r eceived 1 0-year sentences." McNeill, 563 U.S. at 818. When being sentenced in 2009 10 fo r his § 922(g) offense, he contended that those state convictions were not p ro p er 11 predicates for the ACCA enh an c ement because North Carolina had subsequently 12 r educed the maximum sentence for selling cocaine to 38 months and the maximum 13 for possessing c ocaine with intent to sell to 30 months; thus, in 2009, th e m a x imum 14 i mprisonment for those c rimes was not 1 0 years or more. The Supreme C ourt rejected 15 that argument, stating as follows: 16 The plain text of ACCA requires a federal sentencing court 17 to consult the maximum sentence applicable to a d e fendant's 18 previous drug offense at the time of his conviction for that offense. 19 The statute requires the court to determine wheth er a "previous 20 c onvictio[n]" was for a serious drug offense. The o nly w ay to

201 answer this backward-looking question i s to consult the law that 2 applied at the time of that conviction. 3 M cNe i l l, 5 6 3 U.S. at 8 20. Despite the fact that the statutory language defining a 4 serious drug offense u sed the present ten s e- - c alling i t one "for which a maximum 5 term o f imprisonment of ten years or more is prescribed by law," 18 U

. S. C. 6 § 924(e)(2)(A)(ii) (emphasis added)--the C ourt reasoned that o ne could no t kn o w 7 what the maximum penalty was for the offense of which the d efendant had been 8 c onvicted w ithout consulting the statute that w as actually applied to him, see 563 U.S. 9 a t 823. 10 In the present case, the governm ent argues that because the McNeill 11 d efendant's prior state conviction was the focus of a proposed recidivism-related 12 sentencing enhancement, the present case i s " [j]ust like

. . . McNeill

. " (Government's 13 r eply b rief on appeal at 3, 4.) The government points out that the Supreme Court 14 stated that 15 McNeill cannot explain why two defendants who violated 16 § 9 2 2(g) on the same day and who had identical criminal histories17 -down to the dates on which they committed and were sentenced 18 f or their prior offenses--should receive dramatically d ifferent 19 federal sentences solely because one's § 922 ( g ) s entencing 20 happened to occur after the state l egislature amen d ed the 21 punishment for one of the shared prior offenses,

211 M cNeill, 563 U.S. at 823 (em p h a s i s a d ded), and "[t]he g overnment asks the same 2 question here" (Government's reply brief on appeal at 5). 3 But the present case does not in fact involve "the same question." First, 4 " [t]he question in [McNeill ] con c ern [ ed ] how a federal court should determine the 5 m aximum sentence for a prior state dru g offense for A CCA purposes," McNeill, 563 U.S. 6 a t 817 (emphasis added), where the change was one in state l aw, not, as here, a 7 change of federal l a w . I n McNeill, in holding that the district c ourt w as required t o 8 d etermine "the maximum sentence applicable to a defendant's previous drug offense at 9 the time of his c onviction for that offense, " and concluding that the "only way" to do so 10 w as to "consult the law that applied at the time of that conviction," id

. at 820 (emphases 11 a dded), the Court's focus was indeed retrospective; but the focus was not on federal 12 l a w but only on North Carolina law. 13 Thus, while the government a sks us to rule that the d i strict court here 14 w as required to look back to the contents of the CSA schedules at the time of Gibson's 15 New York conviction, McNeill does not point us toward the CSA schedules at all, for 16 federal law--whatever its c ontent was in 2002--was not " the law that applied" t o 17 Gibson's drug offense because Gibson was no t then prosecuted under federal law. 18 Whether or not the CSA schedules in effect at that time were identical to the New

221 Y ork schedules, nothing in federal l aw governed the "sentence applicable" to Gibson 2 for his 2002 violation of N.Y. §§ 220.39(1) and 110. 3 Second, McNeilldid not present the same question as this case because 4 the change in North Carolina law onl y l es s en ed the severity of the punishment 5 pres cribed for a d e fendant's unlawful acts; it did not make a substantive chan g e a s 6 t o what acts were l awful or unlawful. And while the "culpability and dangerousness" 7 indicated by a d efendant's lengthy prior state sentence "does not c ease to exist when 8 a State reformulates its criminal statutes," 563 U.S. at 823 (emphasis added), and "[i]t 9 c annot be correct that subsequent changes in state law can erase an e a rlier conviction 10 for A CCA purposes," i d

. (emphasis added), a defendant's culpability and 11 d angerousness plainly change in the eyes of federal law when the c onduct for which 12 he was previously c onvicted under state law is no l onger unlawful under federal law.

13 2

. The Evolving Classification of Substances 14 F urther, insofar as this case concerns the temporal focus of a court's 15 a ssessment of federal law with respect t o possible enhanced punishment on account 16 o f a defendant's prior c onviction inv o l ving controlled substances, we think it 17 i mportant to begin with the recognition that in enacting the CSA, Congress launched

231 a panorama of c ontrolled substances that i t plainly envisioned wo ul d be ev er2 e volving, not a n unchanging array engraved in stone. The CSA makes it unlawful 3 knowingly o r intentionally to, in t e r alia, "manufacture, distribute, or dispense, or 4 possess with intent to manufacture, distribute, or dispense, a controlled substance." 5 2 1 U.S.C. § 841(a)(1). And the CSA, as enacted in 1970, des i gnated the controlled 6 substances listed in "Schedule[s]" I, II, III, IV, and V, id

. § 812(b), as th e d rugs and 7 oth er substances to which the prohibitions then applied. But while specifying th a t 8 " [t]he term ' c on trolled substance' means a drug or other substance, or immediate 9 precursor, included in schedule I, II, III, IV, o r V [of § 812(b)]," id

. § 802(6), Congress 10 a dded that after October 27, 1970, those schedules " shall be updated and republished 11 o n an annual basis , " i d

. § 812(a) ( emphases added). As a result, " the CSA schedule is 12 a moving target," Do e, 8 8 6 F.3d at 210. Indeed, "since 1 970"--and before 2015-- 13 " 'approximately 160 substances ha[d] been added, removed, or transferred from one 14 schedule t o another.'" I d

. (quo ti ng Ma t t e r of Ferreira, 26 I. & N. Dec. 415, 418 (B.I.A. 15 2 014)). 16 The updating and republication of the schedules of what d rugs or other 17 substances a r e c ontrolled are carried out by the United S tates Attorney General or his 18 D epartment of Justice d esignee, as permissibly authorized by the CSA, which places

241 specific restrictions on the Attorney General's discretion t o define criminal conduct, 2 s ee generally Touby v. United States , 500 U.S. 160, 167 ( 1991). The CSA a lso imposes o n 3 the Attorney General procedura l c o nstr a int s, su ch a s r e qu i red consultation with--and 4 s o me ti mes deference to--the Secretary of Health and Human Services ("Secretary" ) o n 5 scientific and medical issues, and requirements for public notice and o pportunity for 6 c omment prior to the A ttorney General's exercise of his CSA-conferred authority to, 7 i nter alia, add a drug or other substance to a particular schedule or remove a drug or 8 o ther substance from the schedules, see, e.g. , 21 U.S.C. §§ 811, 812, 871(a); see generally 9 T ouby, 500 U.S. at 165-68. These u pdated lists a re published in the C o de o f Federal 10 Regulations, 21 C.F.R. § 1308, and identify elements of Title 21 crimes. 11 With respect to naloxegol, in 2013 the Drug Enforcement A d mini str a ti o n 12 ( "DEA"), the Department of Justice agency to whose Administrato r th e Attorney 13 General had assigned his C SA s chedules functions, requested an evaluation and 14 r ecommendation from the Secretary. The Secretary thereafter, after c onsidering the 15 e ight factors set out in 21 U.S.C. § 811(c), including the subs ta n c e' s abuse potential, 16 l e gitimate medical use, and dependence susceptibility, recommended that naloxegol 17 and i ts salts be r emoved from the CSA schedules. The D EA, after also considering the 18 statutory factor s, a l o ng w ith the Secretary's recommendation, "f[ound] that naloxegol

251 d oes not possess abuse or dependence potential." Naloxegol Delisting Rule, 80 Fed. 2 Reg. at 3468-69. Accordingly, on January 23, 2 0 15 , th e DE A issued the Naloxegol 3 D elisting Rule, r e v i sing CSA Schedule II's paragraph (b)(1) intro d uc tory text to list 4 a s controlled "(1) Opium and opiate, and any salt, compound, derivative, or 5 preparation of opium o r opiate exc l u d i ng . . . naloxegol

. " 21 C.F.R. § 1308.12(b)(1) 6 ( emphases added). 7 In a rguing against Gibson's contention that the governing principle is 8 that the district c ourt should look to the Guidelines that "are in e ffect on the date the 9 d efendant is sentenced," 18 U.S.C. § 3553(a)(4)(A)(ii), and thus should also look to the 10 C SA schedules on the sentencing date in his current federal case, the government 11 states that 12 [t]here is no precedent requiring a d istrict c ourt t o treat the drug 13 schedules, which a re administrative document s inc o rpo r a ted into 14 the statuto ry d efi n ition of a "controlled substance," as if they are 15 somehow part of Sentencing Guidelines. 16 ( Government's brief on a ppeal at 16-17 (emphasis in original).) To the extent that the 17 g overnment suggests that th e C SA s chedules a re incorporated into the CSA, it is 18 c orrect: As indicated above, the C SA-mandated schedules are the lists that are 19 u pdated and r epublished in the Code of Federal Regulations e very year. And while 20 the g overnment argues that th e CSA schedules are not themselves guidelines, and 261 suggests that the district court in sentencing need not consider the CSA schedules, the 2 fact is that the Guidelines themselves u se those schedules, see, e.g. , Guidelines § 2D1.1 3 A pplication Note 3 (" Classification of Controlled Substances

. . . . For the purposes 4 o f the guidelines, the classifica ti o n of the controlled substance under 21 C.F.R. 5 § 1 308.13-15 is the appropriate classification."). The court's first obligation in 6 d etermining an appropriate sentence i s to calculate the proper Guidelines sentence. 7 Se e Gall v. United States , 552 U.S. 38, 49 (2007). In a case involving a controlled 8 substan c e, the court must thus determine whether what is at issue i s a controlled 9 substance. How odd it would be if the district court, in a criminal case referring t o 10 " controlled substances," were no t a t l ea s t implicitly required to consult the CSA 11 schedules that the Guidelines use. 12 In T ownsend, relied on b y the d istrict court in the present case, we held 13 that "[t]he term 'controlled subs tance' in . . . § 4B1.2(b) r efers exclusively to those 14 substances in the CSA," 897 F.3d at 75. Accord United States v. Bautista, 989 F.3d 698, 15 702 (9th Cir. 2021). While the government argued th a t the T ownsend opinion i tself 16 indicates that we were assessing federal law o nly as it stood at the time of Townsend's 17 prior state-law conviction ( see Government's December 2 Mem. at 5-6) and that our 18 C ourt has a pplied such a " time-of-conviction" rule in other criminal cases decided by

271 summary order, we are not persuaded of that characterization of our precedent. W e 2 see some a mbiguity in the latter group of cases which, in any e vent, under our Court 3 rules lack precedential status. See 2d Cir. Local R. 32.1.1(a). In T ownsend itself, there 4 wa s n o express statement as to what version of the CSA schedules was being 5 c onsulted, but the language used does not support the government's interpretation 6 o f a purely retrospective focus. The government asserts that Townsend consulted the 7 "corresponding" CSA schedules "' at the time of ' the state conviction" (Governmen t' s 8 b r i e f on appeal at 14 (citing Townsend, 8 97 F .3d at 74 (emphasis in brief))); but in the 9 sentence the government quotes, Townsend described only the New Y ork law; and in 10 the next sentence Townsend referred to the CSA schedules and used the present tense. 11 S ee 897 F.3d at 74 (" A t the time of Townsend's conviction, the New Y ork state drug s chedule, 12 section 3306 o f the New Y ork Public Health Law, i ncluded HCG as a Schedule III 13 c ontrolled substance. See N.Y. Pub. Heal th Law § 3306, Schedule III[](g) (listing 14 Chorionic gonadotropin). HCG is not a controlled subs tance u nder the CSA ." 15 ( emphases added)). In any event, w e doubt th at T o w n send was faced with a 16 significant choice of versions, as w e have found no reference to HCG in any CSA 17 schedule.

281 In pursuing i ts ti m i ng a rgument that the district court, in d etermining 2 th e G u idelines-recommended sentence for Gibson's current federal crimes, was 3 r equired to look only at the version of the CSA schedules in effect at the time o f 4 Gibson's 2002 suppos ed-predicate crime, the government also argues that 5 whether a substance involved in an offense is "controlled " can 6 only b e answered by examining the drug schedules in effect at the 7 time it i s c ommitted; if the substance is not "controlled" at the time of 8 the offense, then no crime has been committed

. 9 ( Government's brief on appeal at 17 (emphasis added).) 10 B ut in 2002, Gibson was not prosecuted for or convicted of violating a 11 federal l a w as to controlled substances; the 2 002 v ersion of the CSA schedules did not 12 g overn, and had no relevance to, his state-law crime. There was no suggestion of any 13 r elevance o f the C SA to Gibson un ti l h e wa s to be sentenced in 2020 for his present 14 federal bank robbery offenses, when the g overnment requested that he be sentenced 15 t o 151-188 months' imprisonment because o f his 2002 c o ntrolled substance conviction 16 under state law. 17 The career- o ffender enhancement advocated by the government is 18 theoretically not intended to p un i sh Gibson for the crime he committed in 2002, see 19 generally Gryger v. Burke, 33 4 U

. S. 728, 732 (1948); but that would be its effect here, 20 b e cause the conduct in which Gibson engaged in 2002 and for which he was 291 thereafter duly punished--which, under the categorical approach, must be presumed 2 t o have been an attempt to sell naloxegol--is no longer a federal crime. For the federal 3 o ffenses that Gibson c ommitted in 2017 and 2018, the district court concluded that an 4 a ppropriate prison term i s 60 months. Thus, if the 1 88-month maximum prison term 5 u rged by the government were imposed o n Gibson, he would serve not just the five 6 y ears warranted for his present federal crimes, but an additional 10-plus years' 7 i mprisonment o n a c c o unt of the state-law-prohibited conduct for which he has 8 a lready b een punished by the state and which is no longer federally prohibited. W e 9 c onclude that the district court properly rejected the g o vernment's c ontention that the 10 r elevant CSA schedules were those in effect in 2002. 11 Th at said, we note that it is not c lear that in determining wheth er th e 12 state la w applicable to the defendant's prior controlled substance conviction is 13 b r o ader than federal law, the version of the CSA schedules o n which the district court 14 should focus is the version in effect on the date of the defendant's sentencing for his 15 current offense rather than on the d a te o n which he committed his current offense. 16 A defendant's sentencing date is somewhat unpredictable, postponable for example 17 t o accommodate health problems, or to allow c ollection o f additional information for 18 sentencing, or to facilitate a defendant's cooperation with the g o v ernment in other

301 prosecutions. As the McNeill Court observed, multiple d efendants m a y w el l have 2 d ifferent sentencing dates despite having committed their crimes on the same date. 3 S ee 5 6 3 U.S. at 823. 4 The government points to that observation and argues that "focusing o n 5 the drug schedules from the date of [the prior] conviction 'perm its a defendant t o 6 know even before he violates' federal law whether his offense is categorically broader 7 than a federal counterpart . " (Government's reply brief on a ppeal at 5 (quoting McNeill, 8 5 6 3 U

. S. a t 823 (first emphasis in reply brief; second and third emphases ours)).) 9 Indeed, a defendant wh o i s p e rhaps about to "violate[] federal law" and wants "to 10 know . . . before he [acts]" whether his sta te- l a w c o nv iction "is

. . . broader than a 11 fe d e r a l c o unte rp a r t " w ou l d hav e t o kno w the c o nte mpo r ane o u s c o ntent o f that fe d e r a l 12 c ounterpart, i.e. , the law at the time o f his federal o ffense. This is the point in time at 13 which he could choose to refrain from c o nduct whose consequences would depend 14 o n federal criminal law. But, a s d i s cussed above, by law the CSA schedules are 15 u pdated every year. And even a potential federal o ffender who might consult th e 16 c ontempo r ane o u s C SA sche d u l e s t o determine what substances are controlled would 17 l i kely not be a lerted to a need to ferret out decades-old superseded versions of the

311 federal controlled subst an c e sche d u l e s tha t in fact were not applied to his decades-old 2 c onduct. 3 Here, by the time Gibson began his 2017 bank r obbery spree, the CSA 4 schedules, having eliminated naloxegol in 2015, w ere narrower than the New York 5 schedules applicable to his 2002 state-law c o nviction. We have seen no reason t o 6 b e lieve that Congress, which r equired th a t federal "drug schedules"--which are 7 " incorporated into the statutory definition of a ' controlled substance'" (Government 8 b r i e f on appeal at 16-17 ( emphasis in original ) )

- -be updated with appropriate 9 a dditions, reclassifications, and deletions every year, would have intended that such 10 changes in the federal substantive criminal law should be ignored in connection with 11 c o n t r o l l e d

- s u b s t a n c e - r e l a t e d p r i n c i p l e s o f e n h a n c e d s e n t e n c i n g f o r a 12 c ontemporaneous offense. 13 Nonetheless, w e need no t d e c i d e in this case whether, in determining the 14 a pplicability of Guidelines § 4B1.1, the district court should consult the CSA version 15 at the time of the defendant's current o ffense or the version at the ti m e o f h i s 16 sentencing for this offense, since the controlled substance schedules were narrower 17 than state law at both times. Naloxegol was not a co ntro lled substance in the CSA

321 schedules either when Gibson committed his robberies or when he w as sentenced for 2 them.

3 3

. The Government's Reliance on Doe 4 The government also relies o n o ur d ec is i on in Doe, 886 F.3d 2 03, an 5 i mmigration case. The petitioner in that c ase sought r eview o f a d ecision by the 6 B oard of Immigration Appeals affirming an order of removal that was based on his 7 2 014 federal conviction of an aggravated felony, see 8 U .S.C. § § 1227(a)(2)(A )( iii), 8 ( B)(i); id

. §§ 1 101(a)(43)(B), (U), following his plea of guilty to "conspiracy to distribute 9 an d p o ss e ss with intent to distribute heroin, in violation of 21 U .S.C. §§ 846, 10 8 41(b)(1)(C) of the CSA," Doe, 8 86 F.3d at 206. Doe contended that because the DEA 11 r emoved "naloxegol

. . . from the C SA Schedules" in J anuary 2015, during the 12 penden cy o f h is removal proceedings, "his c o nviction no longer categorically 13 involved a controlled substance, as required for his removal." Doe, 886 F.3d a t 206. 14 W e d enied the petition, noting that "the legal question of what a conviction necessarily 15 e stablished" depends on "the CSA S chedules in e ffect at the time of c o nviction," not, 16 " as a rule," on the fortuitous modification of the CSA schedul es a fter he had been 17 c onvicted. Id

. at 209-10 (emphasis in o riginal) (internal quotation marks omitted); see

331 a lso id

. at 210 (noting the intent of the "saving statute," 1 U.S.C. § 109, "to ensure that 2 a convicted criminal defendant does not fortuitously benefit from more lenient laws 3 that may be passed after he or she has been convicted" (internal quota tion marks 4 o mitted)). 5 The g overnment here, referring to Doe's convi c ti o n as "his earlier 6 c onviction," argues that " when determining whether a prior conviction constituted a 7 ' controlled substance offense,' district courts should evaluate the statute as written at 8 the time of that c onviction" ( Government's brief on appeal at 11 (emphases added)); 9 and i t insists that Doe, although an immigration case, involved "the same reasoning" 10 that the government advocates here ( id

. at 8), and that D o e i s thus an "on-point 11 precedent" ( id

. at 12) involving "the same analysis" ( id

. at 12-13). W e disagree, given 12 that the contexts of Doe and th e p res ent case are legally and factually different. 13 L egally, an alien removal proceeding i s not a c riminal prosecution. S ee, e.g. , INS v. 14 Lopez-Mendoza, 4 68 U.S. 1032, 1039 (1984) ( deportation is not punishment); Doe, 886 15 F .3d at 210 ("retroactive deportation does not violate the Ex P ost Facto Clause" 16 ( internal quotation marks omitted)). 17 Nor did the factual circumstances in Doe parallel those here--contrary t o 18 the go v ernment's references to Doe as having an " earlier conviction," " a prior

341 conviction ," a " state conviction" ( G o v ern ment's brief on appeal a t 11-12 (emphases 2 a dded)). We see no indication--either in the pages of Doe cited b y the government or 3 in th e Doe record as a whole--that the petitioner in Doe had more than one criminal 4 c onviction. And that conviction--a judgment sentencing him for a federal violation 5 th a t was an aggravated felony--was necessarily earlier than and prior to th e 6 challenged removal proceeding, given that the proceeding w as based on that 7 c onviction. Doe simply involved the question of whether that conviction was one for 8 an aggra v a ted fel o ny . That question c o uld only be answered by looking at the law 9 that was actually applied. 10 In short, Doe d i d not involve more than o ne set of c onviction s, did not 11 r equire comparison of the laws of two sovereigns, and did not concern punishment. 12 The government's reliance on D oeis misplaced.

13 CONCLUSION

14 We have considered all of the government's a rguments on th i s appeal 15 and have found in them no basis for reversal. The Guidelines § 4B1.1 career-offender 16 enhancement, here premised in part on a 2002 c o nviction under New Y o rk S t a te Penal

351 L aw §§ 220.39(1) and 110, wa s i n a p p licable to Gibson for lack of a necessary 2 predicate. Gibs on was sentenced in 2 020 for bank robbery offenses committed in 3 2 017. The CSA h a d removed naloxegol as a federally c ontrolled substance in 2015, 4 thereby making federal law categorically narrower than the state-law counterpart. 5 The judgment is affirmed.

36