United States v. Chaires

88 F.4th 172

UNITED STATES of America, Appellee, v. Robert J. CHAIRES, Defendant-Appellant.

No. 20-4162

August Term 2021

United States Court of Appeals, Second Circuit

Argued: December 8, 2021

Decided: December 7, 2023

Appeal from the United States District Court for the Northern District of New York, No. 18-cr-21-1, Frederick J. Scullin, Judge.

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.

Before: Carney, Sullivan, and Menashi, Circuit Judges.

Per Curiam:

Robert J. Chaires challenges the procedural and substantive reasonableness of the 120-month sentence imposed by the district court (Scullin, J.) following his plea of guilty to two counts of unlawfully distributing cocaine base in violation of 21 U.S.C. §§ 841(a)(1) and 841(b)(1)(B). On appeal, Chaires principally argues that the district court erred when it found that Chaires's two prior state-court narcotics convictions categorically qualified as predicate offenses for the career offender enhancement under U.S.S.G. § 4B1.1. Based on this Court's intervening decision in United States v. Minter, 80 F.4th 406 (2d Cir. 2023), it is now clear that the district court erred when it sentenced Chaires as a career offender under U.S.S.G. § 4B1.1. As the government concedes, the district court's career offender determination was premised on Chaires's two prior state-court convictions brought under a state provision that is categorically broader than the federal predicate definition in section 4B1.2(b). Those convictions thus cannot serve as predicate offenses to section 4B1.1 and the district court therefore plainly erred when it enhanced Chaires's Guidelines range on that basis. Accordingly, we remand the case for resentencing.

I. BACKGROUND

As relevant here, Chaires has two prior state-court drug convictions. In 2003, he pleaded guilty to the criminal sale of a controlled substance in the third degree under N.Y. Penal Law § 220.39(1) and was ultimately sentenced to eight years' incarceration.¹ In 2008, while he was still on parole for the 2003 conviction, Chaires was arrested for selling powder cocaine and ultimately pleaded guilty to attempting to violate section 220.39(1). Though the court sentenced Chaires to four years' incarceration, he was given an alternative sentence in the form of a three-month drug treatment bootcamp, which he completed in November 2008. About a year after his release from bootcamp, however, Chaires's parole was revoked after a routine search uncovered marijuana and ammunition in his residence. In lieu of a parole hold, Chaires was diverted to a drug treatment facility and then released back into supervision in April 2010. Chaires was ultimately discharged from parole in 2011.

Seven years later, in 2018, Chaires was again arrested for narcotics trafficking, this time by federal agents after he sold approximately eighty grams of crack cocaine to a confidential source. A federal grand jury later indicted Chaires on two counts of distributing crack cocaine in violation of 21 U.S.C. §§ 841(a) and 841 b(1)(B).

On August 31, 2020, Chaires pleaded guilty to both counts. That same day, Chaires filed a written objection to his potential classification as a career offender under section 4B1.1 of the United States Sentencing Guidelines, asserting without elaboration that his 2008 conviction for attempted trafficking did not qualify as a predicate "controlled substance offense" under the career offender enhancement. Chaires mounted another objection in his December 2, 2020 sentencing memorandum, arguing that the 2008 attempt conviction could not serve as a career offender predicate because it was merely an inchoate offense.

The district court sentenced Chaires on December 7, 2020. During that hearing, Chaires's counsel again argued that Chaires's 2008 conviction was for an inchoate offense that could not serve as a career offender predicate. The district court disagreed and found that Chaires qualified as a career offender based on his 2003 and 2008 convictions under section 220.39(1), which yielded an advisory Guidelines range of 188 to 235 months' imprisonment. Nonetheless, the district court ultimately imposed a below-Guidelines sentence of 120 months' imprisonment followed by four years of supervised release.

Chaires timely appealed and we heard argument on December 8, 2021. Our decision was delayed, however, while we waited our turn in a queue of cases involving the categorical approach to narcotics predicates under the Guidelines' career offender enhancement. See U.S.S.G. § 4B1.1. We ultimately decided two of those cases on grounds that go to the heart of the sentencing challenges that Chaires now raises. The first, United States v. Gibson, 55 F.4th 153 (2d Cir. 2022), adhered to on reh'g, 60 F.4th 720 (2d Cir. 2023), affirmed the district court's finding that N.Y.P.L § 220.39(1) is categorically broader than its federal analog and therefore cannot trigger the career offender enhancement under section 4B1.1. After we directed the parties to submit supplemental briefing on whether Gibson was a precedential holding that bound us here, another panel of this Court decided Minter, 80 F.4th 406. At issue there was whether N.Y.P.L. § 220.39(1) - the same provision as here - was categorically broader than the federal drug schedules. Given that the state provision covers certain cocaine isomers that federal law does not, we found that it was. Id. at 410, 413 (citing the federal Controlled Substances Act ("CSA"), 21 U.S.C. § 802). As a result, we concluded that the defendant's convictions under section 220.39(1) could not serve as predicate offenses under the Armed Career Criminal Act ("ACCA"), 18 U.S.C. § 924(e)(1). Minter, 80 F.4th at 407.

The parties have now filed supplemental briefs addressing the significance of Gibson and Minter, and while they continue to dispute whether Gibson is a precedential opinion that is binding on future panels, both agree that Chaires's state-law convictions are not predicate narcotics offenses to section 4B1.1 after Minter.

II.STANDARD OF REVIEW

We review criminal sentences for reasonableness. United States v. Jones, 531 F.3d 163, 170 (2d Cir. 2008). As part of that review, we must "first ensure that the district court committed no significant procedural error, such as failing to calculate (or improperly calculating) the Guidelines range." See Gall v. United States, 552 U.S. 38, 39, 128 S.Ct. 586, 169 L.Ed.2d 445 (2007). To that end, we review the district court's Guidelines calculation de novo, including whether the district court properly determined that the career offender enhancement applies. See United States v. Savage, 542 F.3d 959, 964 (2d Cir. 2008) (citing U.S.S.G. § 4B1.2).

Because the defendant here failed to preserve his sentencing challenge, however, we will reverse only if we find plain error. Under that standard, we consider whether "(1) there is an error; (2) the error is clear or obvious, rather than subject to reasonable dispute; (3) the error affected the appellant's substantial rights; and (4) the error seriously affects the fairness, integrity or public reputation of judicial proceedings." United States v. Miller, 954 F.3d 551, 557-58 (2d Cir. 2020).

III. DISCUSSION

Although Chaires raises a host of challenges to his sentence on appeal, we need only decide whether Chaires's prior state-law convictions under N.Y.P.L § 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 approach" to that comparison, examining the elements of the defendant's conviction and asking whether those elements criminalize any conduct that section 4B1.2(b) does not cover. See United States v. Townsend, 897 F.3d 66, 72 (2d Cir. 2018).

We perform this categorical approach in two steps. See Stuckey v. United States, 878 F.3d 62, 67 (2d Cir. 2017). First, we "identify the 'elements of the statute forming the basis of the defendant's [prior state] conviction.' " Id. (quoting Descamps v. United States, 570 U.S. 254, 257, 133 S.Ct. 2276, 186 L.Ed.2d 438 (2013)).² "In doing so, we examine what is the minimum criminal conduct necessary for conviction under that particular state statute." Id. (alterations and internal quotation marks omitted).

Once we have identified the elements underlying the defendant's prior state conviction, we "compare" those elements with the conduct that constitutes a "controlled substance offense" under section 4B1.2(b) of the career offender enhancement. See Townsend...