Second Circuit Criminal Law Blog

Second Circuit Vacates Sentence, Citing Failure to Apply Categorical Approach and Finding No Predicate Felony Drug Offense

The Second Circuit (Walker, Carney, and Koeltl) issued a decision vacating a 10-year sentence of imprisonment for conspiracy to distribute and possess with intent to distribute marihuana.  The Court held that, contrary to the district court’s finding, a prior conviction for the attempted sale of a controlled substance in the fifth degree, in violation of N.Y. Penal Law (NYPL) § 220.31, was not a conviction for a “felony drug offense,” as defined by 21 U.S.C. § 802(44).  The case, United States of America v. Jeremy L. Thompson, 18-2545-cr, clarifies that courts must use the “categorical approach” when identifying predicate felony drug offenses, and that the Second Circuit will not expand § 802(44)’s reach beyond its enumerated classes of drugs.  Although this case arises in the context of the government’s use of a prior felony information, the Court has employed the same type of categorical analysis we see in cases brought under the Armed Career Criminal Act.


In April 2018, Jeremy Thompson pleaded guilty to conspiracy to distribute and possess with intent to distribute marihuana, in violation of 21 U.S.C. § 846.  The government alleged that the offense involved more than 100 kilograms of marihuana, which would normally carry a 5-year mandatory minimum.  Here, the government filed a prior felony information pursuant to 21 U.S.C. §§ 841(b)(1)(B) and 851, which has the effect of doubling the applicable mandatory minimum sentence.  The prior felony information alerted the district court to Thompson’s 2002 conviction for the attempted sale of a controlled substance in the fifth degree, in violation of NYPL § 220.31, which criminalizes the sale of any of the hundreds of controlled substances enumerated in N.Y. Pub. Health Law § 3306.  Although Thompson admitted to the 2002 conviction and conceded that the prior conviction involved cocaine, he contested whether a violation of NYPL § 220.31 was a “felony drug offense” that would trigger the enhancement in § 841(b)(1)(B).  Thompson argued that (1) the district court was required to use the categorical approach—and therefore could not consider the particular facts relating his crime—to determine whether his prior violation was a felony drug offense, and that (2) NYPL § 220.31 was broader than the federal definition of a felony drug offense. 

The district court rejected both arguments.  First, it held that it was not required to apply the categorical approach.  It asserted that neither the Supreme Court nor the Second Circuit had definitively mandated that approach, and noted that, in its view, 21 U.S.C. § 851(c) provides a fact-finding mechanism for courts to determine whether to enhance a sentence by reason of a prior conviction.  Second, it concluded that, even if the categorical approach were required, Thompson’s argument would fail because the activity criminalized in the New York statute fell within the scope of the federal statute. 

The Circuit’s Decision

The Second Circuit disagreed with the district court and vacated.  Contrary to the district court, it found that a categorical approach must be used in assessing whether a prior conviction is a “felony drug offense” under § 841(b)(1)(B).  The Court noted that the “relevant statutory text [in 21 U.S.C. § 841(b)(1)(B)] is centered upon the fact of conviction and not the facts supporting that conviction,” and that sections 851(a), 851(c), and 802(44) are similarly concerned with the binary question of conviction.  The Court observed that statutory history does not require a different reading:  In enacting previous iterations of § 841(b)(1)(B), “Congress plainly did not intend for courts to use a circumstance-specific approach,” and “[n]othing in the statutory history suggests that Congress departed from its original categorical approach in doing so.” 

The Court then assessed whether Thompson’s NYPL § 220.31 offense “is a categorical match for a felony drug offense under § 802(44), the federal analog.”  It noted that the state statute criminalizes the sale of a wide range of substances, including hCG, a pregnancy hormone.  Because some of the substances regulated by the state statute fall outside the scope of the federal statute, the Court concluded that a conviction under NYPL § 220.31 is not a predicate “felony drug offense” for purposes of § 841(b)(1)(B). 

For these reasons, the Court vacated Thompson’s sentence and remanded the case for resentencing.


The Circuit’s decision will make it marginally less common for the government to file a prior felony information.  Sentencing reformers will greet this decision as a positive development, as the use of prior felony informations by the government to double minimum sentences in narcotics cases has been controversial in some quarters.  There are several reasons for this.  First, some prosecutors threaten to file a prior felony information as a means of inducing a defendant to plead guilty rather than proceed to trial.  Second, there has also has been notable variation across offices in the filing of prior felony informations—some offices use them more than others.  Third, some have questioned the fairness in seeing a sentence enhanced so dramatically based on an old conviction.  The prior state conviction here occurred in 2002, some 16 years before the new federal conviction.  Does this look like a pattern of drug-related misconduct that merits a doubling of the mandatory minimum sentence?  Finally, the conviction that led to the doubling of the sentence is, as the Court recognized, “a relatively low-level Class D felony in the fifth degree.”  In all, a mandatory minimum of five years seems like it is adequate to achieve the purposes of sentencing.

By Ilan Stein and Harry Sandick.