Hylton v. Sessions, 897 F.3d 57

Background

Antoine Hylton, a lawful permanent resident, was convicted in New York of criminal sale of marijuana in the third degree (NYPL § 221.45) for transferring >25 grams aggregate weight. He conceded removability but sought cancellation of removal.
The IJ held Hylton was not an aggravated felon because the minimum conduct under NYPL § 221.45 includes nonremunerative transfers of ~30 grams (an ounce) or less, which the CSA treats as a misdemeanor; the IJ granted cancellation of removal.
The BIA reversed, finding Hylton ineligible for cancellation because his conviction was an aggravated felony, applying a “realistic probability” inquiry rather than a pure elements-based categorical approach.
The Second Circuit reviewed de novo whether the state conviction necessarily constituted a federal felony under the CSA, i.e., whether the minimum conduct criminalized by NYPL § 221.45 is punishable as a federal felony.
The court held that an ounce (≈30 grams) is a “small amount” under 21 U.S.C. § 841(b)(4), NYPL § 221.45 reaches nonremunerative transfers of amounts within that range, and therefore Hylton’s conviction is not categorically an aggravated felony.
The Second Circuit granted the petition, vacated the BIA opinion, and remanded for the BIA to review the IJ’s discretionary grant of cancellation of removal.

Issues

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether the minimum conduct under NYPL § 221.45 is necessarily a federal felony under the CSA	Hylton: NYPL § 221.45 reaches nonremunerative transfers of ≈25–30 grams (≤1 ounce), which the CSA treats as a misdemeanor under § 841(b)(4)	Government: The conviction is an aggravated felony; BIA argues no realistic probability NY would apply § 221.45 to nongeneric (misdemeanor-level) conduct	Held: NYPL § 221.45 punishes conduct that can fall within CSA misdemeanor (§ 841(b)(4)); thus not categorically an aggravated felony
Proper test: categorical elements-only analysis vs. realistic-probability inquiry	Hylton: Court should apply categorical approach, comparing statutory elements only; no need for realistic-probability when statute is facially broader	Government/BIA: Courts should look beyond text and require showing that state would in fact apply statute to nongeneric conduct	Held: Use elements-based categorical approach; realistic-probability test unnecessary where the state statute on its face covers nongeneric conduct
What quantity is a “small amount” under § 841(b)(4)	Hylton: An ounce (~28.35 g; roughly 30 g) is a “small amount,” reflecting personal use/social sharing	Government: (Implicitly) smaller amounts only; BIA relied on out-of-circuit dicta limiting “small amount” to a few cigarettes	Held: An ounce (≈30 grams) is a “small amount” under § 841(b)(4)
Remedy and remand	Hylton: Remand to allow BIA to consider IJ’s discretionary cancellation after finding no aggravated felony	Government: Removal as aggravated felon forecloses cancellation	Held: Petition granted; BIA opinion vacated; case remanded for BIA to review IJ’s grant of cancellation of removal

Key Cases Cited

Moncrieffe v. Holder, 569 U.S. 184 (2013) (when a state marijuana-distribution conviction does not establish remuneration or more than a small amount, it falls into CSA misdemeanor exception)
Martinez v. Mukasey, 551 F.3d 113 (2d Cir. 2008) (categorical approach applied to NY marijuana-sale statute)
Mathis v. United States, 136 S. Ct. 2243 (2016) (no realistic-probability inquiry when state statute’s elements plainly cover broader conduct than federal counterpart)
Duenas-Alvarez v. Gonzales, 549 U.S. 183 (2007) (realistic-probability test explained as a backstop where statutory reach is indeterminate)
Lopez v. Gonzales, 549 U.S. 47 (2006) (state offense is an aggravated felony only if it proscribes conduct punishable as a federal felony)
Harbin v. Sessions, 860 F.3d 58 (2d Cir. 2017) (applying categorical approach to conclude certain NY convictions are not aggravated felonies)