Doe v. Sessions, 886 F.3d 203

John Doe, a Dominican national and lawful permanent resident since 2007, pleaded guilty in 2014 in S.D.N.Y. to conspiracy to distribute heroin under federal CSA provisions pursuant to a cooperation agreement.
After conviction the government charged him removable under the INA as (a) convicted of an offense relating to a controlled substance, (b) a drug‑trafficking aggravated felony, and (c) conspiracy to commit such an aggravated felony.
The CSA defines “controlled substance” by reference to DEA schedules, which were amended in January 2015 to remove naloxegol—a substance that had been within the schedules at the time of Doe’s 2014 conviction. Doe argued this change meant his conviction no longer categorically involved a federally controlled substance.
The IJ and BIA rejected Doe’s motion to terminate on removability grounds, applying a comparison between the statute of conviction and the federal schedules as they existed at the time of conviction. The IJ also denied CAT relief, finding Doe had conceded that only one co‑defendant knew of his cooperation.
On appeal, Doe challenged (1) removability under the categorical approach given the schedule change and (2) the denial of CAT relief. The Second Circuit reviewed the removability question de novo and review of CAT was limited to legal error.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether a federal CSA conviction is assessed against the DEA schedules in effect at time of conviction or at time of removal proceedings	Doe: apply a "time‑of‑decision" rule; compare statute of conviction to CSA schedules in effect during removal (post‑2015 removal, naloxegol removed)	Government/BIA/IJ: apply a "time‑of‑conviction" rule; compare statute of conviction to CSA schedules in effect at conviction	Held: Time‑of‑conviction rule controls; Doe remains removable under his federal CSA conviction.
Whether the agency committed legal error in denying CAT relief by mischaracterizing the record	Doe: IJ/BIA ignored or mischaracterized evidence showing multiple co‑defendants (and others) knew of his cooperation, and relied on a mistaken “concession” that only one co‑defendant knew	Government: IJ/BIA found no clear error in concluding Doe failed to prove likelihood of torture; treated record as showing limited knowledge of cooperation	Held: Agency committed legal error by overlooking and mischaracterizing key record evidence; remanded for reconsideration of CAT claim.

Moncrieffe v. Holder, 569 U.S. 184 (establishes use of categorical approach to compare conviction to federal definition for immigration consequences)
Mellouli v. Lynch, 135 S. Ct. 1980 (discusses comparing state drug statutes to federal CSA schedules in categorical analysis)
Carachuri‑Rosendo v. Holder, 560 U.S. 563 (conviction is the relevant reference point for categorical analysis)
Descamps v. United States, 570 U.S. 254 (describes categorical approach in determining whether a statute criminalizes broader conduct than a generic offense)
Padilla v. Kentucky, 559 U.S. 356 (constitutional norms of fair notice and counsel assistance relevant to immigration consequences)
I.N.S. v. St. Cyr, 533 U.S. 289 (same; retroactivity and notice principles)
Lugo v. Holder, 783 F.3d 119 (2d Cir.) (discusses fair notice and assistance of counsel in immigration consequence context)