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 21 U.S.C. § 841(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 21 U.S.C. § 802(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 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 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 21 U.S.C. § 802(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 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.
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, 974 F.3d 193, 201 n.3 (2d Cir. 2020). De novo
10 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 natural meaning.”
Smith v. United States, 508 U.S. 223, 228 (1993); see Davis, 961 F.3d at 187 (“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, 81 Fed. Reg. 29492 (May 12, 2016). Butyryl fentanyl remains a Schedule I controlled substance. See 21 C.F.R. § 1308.11.
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., 21 U.S.C. § 861(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, 464 U.S. 16, 23 (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, 553 U.S. 285, 304 (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, 129
F.3d 81, 86 (2d Cir. 1997) (employing clear error analysis of relevance
determination for purposes of U.S.S.G. § 1B1.3); United States v. Cacace, 796 F.3d
176, 191 (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, 426 F.3d 556, 562 (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, 233 F.3d 704 (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, 927 F.2d 111, 114 (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, 906 F.2d 867, 873 (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, 927 F.2d at
115 (“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, 862 F.3d 163, 176 (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, 806 F.3d 55, 64
(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., 470 U.S. 564, 573 (1985) (internal quotation
marks omitted); accord Mathie v. Fries, 121 F.3d 808, 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, 470 U.S. at 574, 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.
233 F.3d 704, 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. 233 F.3d at 710. 5
5Of course, judicial findings at sentencing cannot trigger increases in the statutory minimum or maximum penalties. See, e.g., United States v. Ulbricht, 858 F.3d 71, 128 (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 21
U.S.C. § 841(b)(1)(B)(vi) even if it is not a “controlled substance
analogue” under 21 U.S.C. § 802(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.