20-2545 United States v. McCray

In the United States Court of Appeals For the Second Circuit

August Term, 2020 No. 20-2545

UNITED STATES OF AMERICA, Appellee,

v.

TORRI MCCRAY, Defendant-Appellant.

Appeal from the United States District Court for the Western District of New York No. 17-cr-147 — Lawrence J. Vilardo, Judge

ARGUED: JUNE 4, 2021 DECIDED: JULY 29, 2021

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

∗ Judge Rachel P. Kovner, of the United States District Court for the Eastern District of New York, sitting by designation. Defendant-Appellant Torri McCray appeals from a judgment of conviction and sentence entered following his guilty plea, in the United States District Court for the Western District of New York (Lawrence J. Vilardo, J.), to charges related to his possession with intent to distribute, and distribution of, fentanyl and butyryl fentanyl. McCray argues that the district court should have dismissed the count charging him with a violation of

(b)(1)(B) premised on butyryl fentanyl. He maintains that butyryl fentanyl is not an “analogue” of fentanyl under § 841(b)(1)(B) because butyryl fentanyl is listed as a controlled substance on the federal drug schedules and is therefore excluded from the definition of “controlled substance analogue” in

(32). Additionally, McCray argues that the district court clearly erred in finding that he was responsible through relevant conduct for a death and abused its discretion when enhancing his sentence pursuant to United States Sentencing Guidelines § 5K2.1. We find no merit in any of these claims. AFFIRMED.

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

2 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

(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

(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 indictment 1 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

(32), which

1Although the motion to dismiss concerned Counts Two and Three, Count Three was dismissed as part of the disposition and is not at issue on appeal.

3 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.

4 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

(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

(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.

5 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

6 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

2 U.S.S.G. § 5K2.1 provides:

If death resulted, the court may increase the sentence above the authorized guideline range.

Loss of life does not automatically suggest a sentence at or near the statutory maximum. The sentencing judge must give consideration to matters that would normally distinguish among levels of homicide, such as the defendant’s state of mind and the degree of planning or preparation. Other appropriate factors are whether multiple deaths resulted, and the means by which life was taken. The extent of the increase should depend on the dangerousness of the defendant’s conduct, the extent to which death or serious injury was intended or knowingly risked, and the extent to which the offense level for the offense of conviction, as determined by the other Chapter Two guidelines, already reflects the risk of personal injury. For example, a substantial increase may be appropriate if the death was intended or knowingly risked or if the underlying offense was one for which base offense levels do not reflect an allowance for the risk of personal injury, such as fraud.

7 “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,

8 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

9 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,

, 201 n.3 (2d Cir. 2020). De novo

10 review similarly applies to questions of statutory interpretation, United States v.

Davis,

(2d Cir. 2020), and challenges to the constitutionality of a

statute, United States v. Hassan,

(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 natural meaning.”

Smith v. United States,

(1993); see Davis,

(“We

begin . . . with the language of the statute, giving the statutory terms their ordinary

or natural meaning.”). Webster’s New Collegiate Dictionary defines “analogue” in

the relevant chemistry context as “a chemical compound structurally similar to

another but differing often by a single element of the same valence and group of

the periodic table as the element it replaces.” (9th ed. 1985). McCray does not

dispute that butyryl fentanyl is an “analogue” of fentanyl under this definition—

11 and indeed, he expressly admitted that butyryl fentanyl is a fentanyl analogue

during his guilty plea. Accordingly, we reject his challenge to the application of

the enhanced penalty provision at § 841(b)(1)(B)(vi).

McCray urges us to look not to the dictionary to define the term “analogue”

but to the definition of “controlled substance analogue” in § 802(32). Section

802(32) states that “the term ‘controlled substance analogue’ means a substance []

the chemical structure of which is substantially similar to the chemical structure

of a controlled substance in schedule I or II . . . [but] does not include [] a controlled

substance.” McCray reasons that, under this definition, butyryl fentanyl is not an

“analogue” of fentanyl because butyryl fentanyl is listed as a controlled substance 3

and § 802(32) excludes controlled substances from the definition of “controlled

substance analogue.” But nowhere in § 841(b)(1)(B)(vi) does the term “controlled

substance analogue” appear; and where that specialized term does not appear, we

3At the time of McCray’s offense conduct, federal drug schedules had temporarily designated butyryl fentanyl as a Schedule I controlled substance. See Schedules of Controlled Substances: Temporary Placement of Butyryl Fentanyl and Beta-Hydroxythiofentanyl Into Schedule I,

(May 12, 2016). Butyryl fentanyl remains a Schedule I controlled substance. See

.

12 have no reason to apply its specialized definition. Rather, Congress wrote

§ 841(b)(1)(B)’s enhanced penalty to apply to “any analogue of [fentanyl].” And,

because Congress did not define “analogue” or “any analogue of [fentanyl],” we

employ the word’s ordinary meaning when interpreting the statute.

McCray contends that declining to use the definition of “controlled

substance analogue” here would render § 802(32) superfluous, but that is plainly

not the case. Congress used the term of art “controlled substance analogue”

elsewhere in the subchapter, see, e.g.,

(d)(1), and even elsewhere in

§ 841 itself. For example, just a few paragraphs later in § 841(b)(7)(A), Congress

outlined a penalty structure for distributing a “controlled substance or controlled

substance analogue” with the intent to commit a crime of violence. Elsewhere in

§ 841(g)(2)(A)(i), Congress defined the term “date rape drug” as “gamma

hydroxybutyric acid (GHB) or any controlled substance analogue of GHB, including

gamma butyrolactone (GBL) or 1,4-butanediol.” (emphasis added). “Where

Congress includes particular language in one section of a statute but omits it in

another section of the same Act, it is generally presumed that Congress acts

13 intentionally and purposely in the disparate inclusion or exclusion.” Russello v.

United States,

(1983) (internal quotation marks and alteration

omitted). Thus, we do not nullify § 802(32) when we interpret § 841(b)(1)(B)(vi)’s

“analogue” according to its ordinary meaning.

Finally, we reject McCray’s argument that § 841(b)(1)(B)(vi) fails to provide

him with sufficient notice that it imposes an enhanced penalty for the crimes of

possessing and distributing 10 grams or more of butyryl fentanyl. “A conviction

fails to comport with due process if the statute under which it is obtained fails to

provide a person of ordinary intelligence fair notice of what is prohibited . . . .”

United States v. Williams,

(2008). That is not the case here. Section

841(b)(1)(B)(vi) states that dealing in 10 grams or more of “any analogue of

[fentanyl]” is subject to an enhanced penalty. McCray does not dispute that

butyryl fentanyl is such an analogue under the ordinary meaning of the word.

14 Thus, we reject his challenge and hold that the statute provides him with fair notice

and satisfies the Fifth Amendment’s requirement of due process. 4

III. The district court did not clearly err or abuse its discretion in applying U.S.S.G. § 5K2.1.

We review for clear error both the district court’s conclusion that McCray’s

November 21, 2016, sale was relevant to his offense conduct and the court’s finding

that the victim’s death resulted from that sale. See United States v. LaBarbara,

(2d Cir. 1997) (employing clear error analysis of relevance

determination for purposes of U.S.S.G. § 1B1.3); United States v. Cacace,

(2d Cir. 2015) (reviewing factual finding at sentencing for clear error). We

review the district court’s decision to depart from the Guidelines range for abuse

of discretion. United States v. Fuller,

(2d Cir. 2005).

McCray raises three related arguments in challenging the district court’s

application of the U.S.S.G. § 5K2.1 enhancement. First, McCray asserts that the

district court clearly erred in finding that McCray’s November 21, 2016, fentanyl

4As noted above, no statutory definition for “analogue” exists, and we are not convinced that § 802’s definition of the separate phrase “controlled substance analogue,” which does not appear in § 841(b)(1)(B)(vi), somehow applies.

15 sale was relevant to the 2017 offense conduct. He maintains that the intervening

hiatus in sales and the differences in the details of the sales—including as to drug

quantity, sale frequency, and the involvement of the Government—significantly

distinguished the November 21, 2016, sale from the charged pattern of 2017

controlled buys. Second, McCray argues that, even if the November 21, 2016, sale

was relevant conduct, the court (a) clearly erred in concluding that the

Government proved by a preponderance of the evidence that McCray supplied

the fatal drugs and then (b) abused its discretion by imposing an enhanced

sentence that the weight of the evidence did not support. Third, McCray contends

that, even if the Government’s evidence met the preponderance standard, due

process requires the Government to shoulder a higher burden of proof, such as by

clear and convincing evidence or beyond a reasonable doubt. For the reasons

below, we find each of McCray’s arguments unpersuasive.

First, we reject McCray’s argument that the court clearly erred in finding

that the November 21, 2016, sale was relevant to his offense conduct. Pursuant to

U.S.S.G. § 5K2.1, the district court may “increase the sentence above the

16 authorized guideline range” where it finds that death resulted from a defendant’s

relevant conduct. See, e.g., United States v. Cordoba-Murgas,

(2d Cir.

2000). Conduct is relevant where it constitutes “the same course of conduct or

common scheme or plan as the offense of conviction.” U.S.S.G. § 1B1.3.

“Offenses . . . may . . . qualify as part of the same course of conduct if they are

sufficiently connected or related to each other as to warrant the conclusion that

they are part of a single episode, spree, or ongoing series of offenses.”

U.S.S.G. § 1B1.3, cmt. n.5(B). Pertinent factors to this assessment include “the

degree of similarity of the offenses, the regularity (repetitions) of the offenses, and

the time interval between the offenses.” Id.

Here, the 2017 controlled buys occurred within McCray’s existing drug-

dealing relationship to the Buyer—involving the same drug (fentanyl), the same

method of payment (cash), and the same principal characters (McCray and the

Buyer) as the November 21, 2016, deal. Although the 2017 controlled buys

occurred approximately six months after the Buyer’s last 2016 buy and involved

greater quantities of fentanyl than the Buyer’s daily 2016 buys did, these

17 differences alone did not sufficiently transform the offense conduct into a distinct

series of offenses. See United States v. Perdomo,

(2d Cir. 1991)

(affirming a finding of relevance despite the relevant conduct involving “a large

quantity of cocaine” and the offense conduct involving “a much smaller

quantity”); United States v. Santiago,

(2d Cir. 1990) (“The fact that

a period of some eight months had elapsed before a controlled buy could be

arranged did not preclude a finding that [the defendant’s] attempt to sell . . . for

the 13th time was part of the same course of conduct as his prior 12 sales.”).

Similarly, the involvement of the Government in the controlled buys did not mark

the beginning of a new and separate course of conduct. See Perdomo,

(“The ‘same course of conduct’ concept . . . looks to whether the defendant

repeats the same type of criminal activity over time. It does not require that acts

be ‘connected together’ by common participants or by an overall scheme.”). Thus,

it was not clear error for the district court to find that the 2016 sales—including the

November 21, 2016, sale—and 2017 controlled buys constituted an “ongoing series

of offenses.” U.S.S.G. § 1B1.3.

18 We next reject McCray’s contention that the evidence presented to the

district court was “so unreliable” that crediting it amounted to clear error. To

begin, we reiterate that “[t]he ability of the district judge—who has seen and heard

the witness—to make credibility determinations is superior to that of the appellate

court.” United States v. Delacruz,

(2d Cir. 2017). The district court

here made specific credibility findings on the record, explaining that the Buyer

“impressed the Court as a credible, knowledgeable, and concerned witness,” “did

not [waver] or hesitate,” “showed no signs of confusion or doubt,” and “did not

attempt to overstate what he knew.” Joint App’x at 474. The record amply

supports the district court’s assessment.

McCray specifically argues that the Buyer’s character, testimonial

inconsistencies, and courtroom identification of his missing bag of drugs render

his entire testimony incredible. But we have previously stated that the sentencing

court has “considerable discretion in resolving evidentiary inconsistencies” and

that “a factfinder who determines that a witness has been inaccurate, contradictory

and even untruthful in some respects may nevertheless find the witness entirely

19 credible in the essentials of his testimony.” United States v. Messina,

(2d Cir. 2015) (internal quotation marks omitted). At best, McCray’s arguments

cast a faint shadow of doubt on the Buyer’s credibility, yet our standard of clear

error review does not permit us to reverse unless “[we] on the entire evidence [are]

left with the definite and firm conviction that a mistake has been committed.”

Anderson v. City of Bessemer City, N.C.,

(1985) (internal quotation

marks omitted); accord Mathie v. Fries,

, 811–12 (2d Cir. 1997). Because

it was entirely “permissible” for the court to credit the Buyer’s testimony about

the events leading up to the victim’s death, Anderson,

, we find no

clear error in the district court’s decision to do so.

We also reject McCray’s argument that the weight of the evidence did not

support the district court’s 30-month upward departure. As we stated in United

States v. Cordoba-Murgas, the standard of proof for the district court’s factual

findings at sentencing, including when considering a departure under

U.S.S.G. § 5K2.1 based on uncharged conduct, is a preponderance of the evidence.

, 710 (2d Cir. 2000). A district court should, however, take into

20 consideration the degree of proof satisfied beyond a preponderance when

exercising its discretion to decide whether and how much to depart. Id. at 709.

Here, the Government’s evidence easily surpassed the preponderance

standard to show that McCray’s November 21, 2016, sale resulted in the victim’s

death. It is undisputed that the victim died of a fentanyl overdose, and the Buyer’s

testimony provided a substantial basis upon which to conclude that McCray’s

fentanyl was responsible. The Buyer told the court that, among other things:

McCray had been selling the victim and the Buyer fentanyl; the only drugs the

victim had access to and injected on the day of his death were purchased from

McCray; the drugs purchased resembled the drugs the Buyer and the victim had

bought from McCray in the past, but were stronger than usual; the victim

disappeared—along with the remaining drugs—while the Buyer was sleeping;

and the bag of drugs recovered from the victim’s person matched the bag the

Buyer purchased from McCray. Having credited the Buyer’s testimony, the district

court did not clearly err when concluding that McCray’s actions led to the victim’s

fatal overdose.

21 Furthermore, there is no indication in the record that the district court

decided to upwardly depart by 30 months under U.S.S.G. § 5K2.1 “without regard

to the weight of the evidence proving the relevant conduct.” Id. at 708. Given the

weight of the evidence showing McCray’s culpability in the victim’s death, we

consider the 30-month upward departure to be only a moderate enhancement of

McCray’s sentence that the district court was well within its discretion to impose.

We see no mismatch between the strength of the evidence presented and the

court’s carefully selected departure, and thus we see no abuse of discretion.

Finally, we reject McCray’s argument that due process required the district

court to apply a higher standard of proof than a preponderance of the evidence.

Cordoba-Murgas forecloses this argument and clarifies that the application of a

more stringent standard, such as a clear and convincing evidence standard, would

in fact constitute error.

. 5

5Of course, judicial findings at sentencing cannot trigger increases in the statutory minimum or maximum penalties. See, e.g., United States v. Ulbricht,

(2d Cir. 2017).

22 IV. Conclusion

In sum, we hold as follows:

1. A substance can be an “analogue” of fentanyl for the purposes of

(b)(1)(B)(vi) even if it is not a “controlled substance

analogue” under

(32).

2. Section 841(b)(1)(B)(vi) provides fair notice that dealing in 10 grams or

more of a substance that is an “analogue” of fentanyl under the ordinary

meaning of the word—even if that substance is not a “controlled

substance analogue”—is subject to the subsection’s enhanced penalty.

3. The district court did not clearly err in concluding that the November 21,

2016, sale was relevant to McCray’s offense conduct or in finding that the

victim’s death resulted from the sale.

4. The district court did not abuse its discretion when departing upwards

from the Guidelines range by 30 months based on the weight of the

evidence that McCray sold the fentanyl that killed the victim.

5. The district court appropriately applied the preponderance of the

evidence standard when making factual findings at sentencing.

23 We therefore AFFIRM the district court’s July 22, 2020, judgment of

conviction and sentence.

24