United States v. McCray

7 F.4th 40

UNITED STATES of America, Appellee,

v.Torri MCCRAY, Defendant-Appellant.

No. 20-2545

August Term, 2020

United States Court of Appeals, Second Circuit.

Argued: June 4, 2021

Decided: July 29, 2021

Timothy P. Murphy, Assistant Federal Public Defender, for Marianne Mariano, Federal Public Defender for the Western District of New York, Buffalo, NY, for Defendant-Appellant

MoniCa J. Richards, Assistant United States Attorney, for James P. Kennedy, Jr., United States Attorney for the Western District of New York, Buffalo, NY, for Appellee

Before: LOHIER, NARDINI, Circuit Judges, and KOVNER, District Judge.^*

William J. Nardini, Circuit Judge:

Defendant-Appellant Torri McCray pleaded guilty to one count of possession with intent to distribute and distribution of fentanyl, in violation of 21 U.S.C. § 841(a)(1) and (b)(1)(C), and one of two charged counts of possession with intent to distribute and distribution of 10 grams or more of butyryl fentanyl, in violation of 21 U.S.C. § 841(a)(1) and (b)(1)(B). McCray now appeals from both his conviction and his sentence imposed in the United States District Court for the Western District of New York (Lawrence J. Vilardo, J. ).

McCray first argues that the district court should have dismissed Count Two of the indictment¹ charging a violation of § 841(b)(1)(B) premised on butyryl fentanyl. Specifically, he maintains that the enhanced penalty provision in § 841(b)(1)(B)(vi), which applies to crimes involving 10 grams or more of "any analogue of [fentanyl]," does not extend to crimes involving butyryl fentanyl because butyryl fentanyl is not an "analogue" of fentanyl. McCray points to the definition of "controlled substance analogue" in 21 U.S.C. § 802(32), which excludes substances that are themselves listed as controlled substances on the federal drug schedules. Relying on this definition, he reasons that, because butyryl fentanyl is listed as a controlled substance, it is not a "controlled substance analogue" and therefore cannot be an "analogue" of fentanyl within the meaning of § 841(b)(1)(B)(vi). He further argues that any alternate definition of "analogue" that includes a listed controlled substance is unconstitutional for failure to provide adequate notice of the scope of illegal conduct.

McCray also asserts that the district court clearly erred and abused its discretion when applying a sentencing enhancement pursuant to United States Sentencing Guidelines ("Guidelines" or "U.S.S.G.") § 5K2.1. Specifically, McCray contends that the district court premised the enhancement on a clearly erroneous factual finding that a death resulted from his relevant conduct, and that it abused its discretion by applying the enhancement against the weight of the evidence.

We disagree as to both challenges. As explained more fully below, we affirm both McCray's conviction and sentence.

I. Background

On August 15, 2017, a grand jury returned a three-count indictment charging McCray with:

• Count One—possession with intent to distribute and distribution of fentanyl, in violation of 21 U.S.C. § 841(a)(1) and (b)(1)(C) ; and

• Counts Two and Three—possession with intent to distribute and distribution of 10 grams or more of butyryl fentanyl, in violation of 21 U.S.C. § 841(a)(1) and (b)(1)(B).

The charges arose from a series of controlled buys the Government made—using a confidential source ("the Buyer")—in June and July of 2017. During the first purchase, the Buyer purchased $600 worth of a substance later determined to be approximately five grams of fentanyl, butyryl fentanyl, furanyl fentanyl, and U-47700. During the second and third purchases, the Buyer purchased $1,000 and $1,400 worth of what testing revealed to contain approximately 11 grams and 15 grams of butyryl fentanyl. McCray was arrested on August 16, 2017.

McCray moved to dismiss Counts Two and Three of the indictment on the same grounds that he argues on appeal—that the definition of "controlled substance analogue" in § 802(32) excludes butyryl fentanyl from the scope of § 841(b)(1)(B)(vi) ’s enhanced penalty. The magistrate judge (Jeremiah J. McCarthy, M.J. ) agreed and recommended that the district court grant McCray's motion to the extent it sought to dismiss the enhanced penalty allegation. The Government objected, and the district court ultimately rejected the magistrate judge's recommendation and denied the motion to dismiss. The district court reasoned that § 802(32) ’s definition of "controlled substance analogue" did not apply to § 841(b)(1)(B)(vi) because the penalty provision used the general term "analogue," not the specially defined term "controlled substance analogue." Considering the ordinary meaning of "analogue," the district court concluded that butyryl fentanyl was, for the purposes of § 841(b)(1)(B)(vi), not excluded from the definition of an "analogue" of fentanyl.

In February 2019, McCray pleaded guilty to Counts One and Two. In exchange, the Government agreed to move to dismiss Count Three. In the plea agreement, McCray reserved the right to appeal the district court's denial of his motion to dismiss Counts Two and Three, and the Government reserved the right to argue for an upward departure from the contemplated Guidelines range of 60 months under U.S.S.G. § 5K2.1 for relevant conduct that resulted in a death.²

In preparation for sentencing and in anticipation of the Government's request for an upward departure pursuant to U.S.S.G. § 5K2.1, the district court held an evidentiary hearing at which the Government presented evidence that McCray's relevant conduct led to the fatal overdose of one of his customers (the "victim") on November 21, 2016. Specifically, the court heard the following details from the Buyer, who had been a customer of McCray before participating in the controlled buys and considered the victim to be his best friend.

The Buyer told the court that beginning in early 2016, he started purchasing one or two grams of what he thought was heroin from McCray daily. The drugs always were packaged similarly, were the same color and texture, and produced the same overall effect when used. Although he initially thought he was buying heroin, the Buyer came to believe that McCray was selling him fentanyl after he tested positive for fentanyl at least 30 times during his weekly outpatient drug tests and never tested positive for heroin. The Buyer testified that he told McCray three times that he had tested positive for fentanyl, but that McCray maintained that he was selling heroin.

The Buyer also told the court that he sometimes bought drugs from McCray for the victim, with whom he used every day and who would often accompany the Buyer to pick up the drugs. On two or three occasions, when McCray could not supply them, the Buyer and the victim obtained drugs from one other dealer, but the Buyer testified that the last time they bought from that dealer was at least one or two months before the victim died. The Buyer stated that he and the victim were close enough that he would have known if the victim had obtained drugs from a third dealer and that to his knowledge the victim had not.

The Buyer testified that on the morning of November 21, 2016, the day the victim fatally overdosed on fentanyl, he and the victim bought about half a gram of drugs from McCray that resembled—in packaging, appearance, and smell—drugs McCray had previously sold. Both men were experiencing withdrawal, so on the way back to the Buyer's home they stopped to get high. They used again when they arrived. The Buyer testified that they remarked that the drugs seemed a little stronger than usual, and then the Buyer passed out. When he awoke a few hours later, the victim and the remaining drugs were gone. The Buyer left to look for the victim and his drugs but did not find either. The Buyer told the court that the police notified him of the victim's death later that evening, and that they also informed him that the victim had been found with a bag of chunky brown powder that matched the Buyer's description of his missing drugs. During the evidentiary hearing, the Buyer identified the recovered bag as the one he purchased from McCray. The Buyer then testified that, in early 2017, he began to cooperate with the Drug Enforcement Administration in an effort to hold McCray responsible for the victim's death.

Following the evidentiary hearing, the district court issued a written decision, finding by a preponderance of the evidence that the victim's death resulted from McCray's relevant conduct and concluding that it therefore could increase McCray's sentence above the Guidelines range pursuant to U.S.S.G. § 5K2.1. On July 14, 2020, the court sentenced McCray principally to a 90-month term of imprisonment—departing upwards by 30 months. The court explained that it chose to depart not just because McCray's drug dealing led to a death, but also because McCray continued to deal even after the Buyer told him that the "heroin" he was selling was actually fentanyl.

II. A substance can be an "analogue" of fentanyl under § 841(b)(1)(B)(vi) even if it is not a "controlled substance analogue" under § 802(32).

We review de novo a district court's denial of a motion to dismiss charges in an indictment. United States v. Walker , 974 F.3d 193, 201 n.3 (2d Cir. 2020). De novo review similarly applies to questions of statutory interpretation, United States v. Davis , 961 F.3d 181, 186 (2d Cir. 2020), and challenges to the constitutionality of a statute, United States v. Hassan , 578 F.3d 108, 119 (2d Cir. 2008).

Section 841(b)(1)(B)(vi) imposes an enhanced penalty for a § 841(a)(1) drug crime where the crime involves "10 grams or more of a mixture or substance containing a detectable amount of any analogue of [fentanyl]." Neither § 841 nor the definitional statute— 21 U.S.C. § 802 —defines the term "analogue" or the phrase "any analogue of [fentanyl]." Where, as here, "a word is not defined by statute, we normally construe it in accord with its ordinary or...