7 F.4th 40
2d Cir.2021Background
- Torri McCray was indicted on: (1) distribution/possession with intent to distribute fentanyl, and (2) distribution/possession with intent to distribute 10+ grams of butyryl fentanyl (enhanced penalty under 21 U.S.C. § 841(b)(1)(B)(vi)).
- Butyryl fentanyl had been temporarily and remains listed as a Schedule I controlled substance by federal regulation.
- Controlled buys in 2017 (using a confidential source) recovered multiple fentanyl analogues including substantial amounts of butyryl fentanyl; a separate November 21, 2016 sale preceded a fatal fentanyl overdose of the Buyer’s friend (the victim).
- McCray moved to dismiss the enhanced-count allegation, arguing that § 802(32)’s definition of “controlled substance analogue” excludes a listed controlled substance like butyryl fentanyl; the district court denied the motion.
- McCray pleaded guilty but reserved the right to appeal the denial. At sentencing the district court found by a preponderance that McCray’s 11/21/2016 sale was relevant conduct that caused the victim’s death and imposed a 30‑month upward departure under U.S.S.G. § 5K2.1 (resulting in a 90‑month term).
- McCray appealed arguing (1) butyryl fentanyl cannot qualify as an “analogue” under § 841(b)(1)(B)(vi) because it is a scheduled controlled substance, and (2) the district court clearly erred in the death finding and abused its discretion in applying the § 5K2.1 enhancement.
Issues
| Issue | Plaintiff's Argument (Government) | Defendant's Argument (McCray) | Held |
|---|---|---|---|
| Whether "analogue" in § 841(b)(1)(B)(vi) includes a substance that is itself scheduled | "Analogue" should be given its ordinary meaning; butyryl fentanyl is an analogue of fentanyl | § 802(32) excludes scheduled substances from "controlled substance analogue," so butyryl fentanyl cannot be an "analogue" for enhanced penalty | The ordinary meaning of "analogue" governs; butyryl fentanyl qualifies; § 802(32) (the term of art) does not control here |
| Void-for-vagueness / fair notice of enhanced penalty | Statute gives fair notice; butyryl fentanyl plainly an analogue under ordinary meaning | Applying "analogue" to a scheduled substance is unconstitutionally vague | Rejected; statute provides fair notice and meets due process |
| Whether the Nov. 21, 2016 sale is relevant conduct to 2017 offenses | The 2016 sale and 2017 controlled buys form the same course of conduct (same buyer, drug, relationship) | Hiatus, quantity differences, and controlled-buys context show separate series of offenses | No clear error: the sales were sufficiently connected to qualify as the same course of conduct under U.S.S.G. § 1B1.3 |
| Whether the district court clearly erred / abused discretion in finding the death resulted from McCray’s sale and in applying § 5K2.1 (and whether preponderance is adequate) | Buyer’s credible testimony and circumstantial links meet preponderance; preponderance is the correct standard; 30‑month departure reasonable | Buyer unreliable; evidence insufficient; due process requires a higher burden; departure unsupported | No clear error or abuse of discretion; factual findings supported by preponderance; preponderance is the appropriate standard |
Key Cases Cited
- Smith v. United States, 508 U.S. 223 (1993) (use ordinary meaning for undefined statutory terms)
- Russello v. United States, 464 U.S. 16 (1983) (different phrasing in same statute implies different meaning)
- United States v. Cordoba-Murgas, 233 F.3d 704 (2d Cir. 2000) (preponderance standard for sentencing findings about uncharged conduct)
- United States v. Perdomo, 927 F.2d 111 (2d Cir. 1991) (quantity differences do not preclude same-course-of-conduct finding)
- United States v. Santiago, 906 F.2d 867 (2d Cir. 1990) (time gaps do not necessarily defeat course-of-conduct link)
- Anderson v. City of Bessemer City, N.C., 470 U.S. 564 (1985) (appellate clear-error standard for factual findings)
- United States v. Delacruz, 862 F.3d 163 (2d Cir. 2017) (trial court’s credibility determinations at sentencing are entitled to deference)