Opposition Brief — Medardo Queg Santos, Petitioner v. United States

No. 21-1418

In the Supreme Court of the United States

MEDARDO QUEG SANTOS, PETITIONER

v.

UNITED STATES OF AMERICA

ON PETITION FOR A WRIT OF CERTIORARI

TO THE UNITED STATES COURT OF APPEALS

FOR THE ELEVENTH CIRCUIT

BRIEF FOR THE UNITED STATES IN OPPOSITION

ELIZABETH B. PRELOGAR

Solicitor General

Counsel of Record

KENNETH A. POLITE, JR.

Assistant Attorney General

DAVID M. LIEBERMAN

Attorney

Department of Justice

Washington, D.C. 20530-0001

SupremeCtBriefs@usdoj.gov

(202) 514-2217

QUESTIONS PRESENTED

1. Whether the district court properly instructed

the jury that it could find petitioner guilty of unauthorized distribution of controlled substances, in violation of

21 U.S.C. 841(a), if it found that petitioner knew he was

distributing controlled substances not for a legitimate

medical purpose and not in the usual course of professional practice.

2. Whether the district court plainly erred in admitting the testimony of an expert witness that petitioner’s

prescribing practices failed to comply with normal standards of medical practice.

3. Whether the district court erred in considering

conduct that it found to be established by a preponderance of the evidence in determining petitioner’s advisory Sentencing Guidelines range.

(I)

TABLE OF CONTENTS

Page

Opinions below .............................................................................. 1

Jurisdiction .................................................................................... 1

Statement ...................................................................................... 2

Argument....................................................................................... 9

Conclusion ................................................................................... 21

TABLE OF AUTHORITIES

Cases:

Alleyne v. United States, 570 U.S. 99 (2013) ...................... 16

Butler v. United States, 565 U.S. 1063 (2011) .................... 16

Chandia v. United States, 568 U.S. 1011 (2012) ................. 16

Cheek v. United States, 498 U.S. 192 (1991) ....................... 14

Culberson v. United States, 562 U.S. 1289 (2011) .............. 16

Gibson v. United States, 559 U.S. 906 (2010) ..................... 16

Greer v. United States, 141 S. Ct. 2090 (2021) .................... 15

Idelfonso v. United States, 139 S. Ct. 178 (2018) ............... 16

Kumho Tire Co. v. Carmichael, 526 U.S. 137 (1999) ......... 12

Lee v. United States, 565 U.S. 829 (2011) ........................... 16

McCray v. United States, 142 S. Ct. 1373 (2022) ............... 16

O’Bryant v. United States, 577 U.S. 987 (2015) ................. 16

Parlor v. United States, 142 S. Ct. 623 (2021) .................... 16

Puckett v. United States, 556 U.S. 129 (2009) .............. 11, 14

Ruan v. United States, 142 S. Ct. 2370 (2022) .... 9, 10, 11, 14

Siegelman v. United States, 577 U.S. 1092 (2016) ............. 16

United States v. Aguilar-Ibarra,

740 F.3d 587 (11th Cir. 2014) ............................................... 8

United States v. Azmat,

805 F.3d 1018 (11th Cir. 2015), cert. denied,

578 U.S. 979 (2016)................................................................ 8

United States v. Booker, 543 U.S. 220 (2005) ............... 16, 18

(III)

IV

Cases—Continued:

Page

United States v. Bras, 483 F.3d 103 (D.C. Cir. 2007) ........ 17

United States v. Brika,

487 F.3d 450 (6th Cir.), cert. denied,

552 U.S. 938 (2007).............................................................. 19

United States v. Buchan,

No. 19-50272, 2021 WL 4988020

(9th Cir. Oct. 27, 2021) ........................................................ 20

United States v. Culver,

598 F.3d 740 (11th Cir.), cert. denied,

562 U.S. 896 (2010).............................................................. 17

United States v. Fisher,

502 F.3d 293 (3d Cir. 2007), cert. denied,

552 U.S. 1274 (2008)...................................................... 18, 20

United States v. Garcia, 439 F.3d 363 (7th Cir. 2006) ....... 17

United States v. Grier,

475 F.3d 556 (3d Cir.), cert. denied,

552 U.S. 848 (2007).............................................................. 17

United States v. Grubbs,

585 F.3d 793 (4th Cir. 2009), cert. denied,

559 U.S. 1022 (2010)...................................................... 17, 19

United States v. Johnston, 268 U.S. 220 (1925).................. 12

United States v. Kikumura,

918 F.2d 1084 (3d Cir. 1990) .............................................. 18

United States v. Kilby, 443 F.3d 1135 (9th Cir. 2006) ....... 17

United States v. Lovern,

590 F.3d 1095 (10th Cir. 2009) ........................................... 14

United States v. Magallanez,

408 F.3d 672 (10th Cir.), cert. denied,

546 U.S. 955 (2005).............................................................. 17

United States v. Mares,

402 F.3d 511 (5th Cir.), cert. denied,

546 U.S. 828 (2005).............................................................. 17

United States v. Moore, 423 U.S. 122 (1975) ...................... 15

V

Cases—Continued:

Page

United States v. Parlor,

2 F.4th 807 (9th Cir.), cert. denied,

142 S. Ct. 623 (2021) ........................................................... 19

United States v. Reuter,

463 F.3d 792 (7th Cir. 2006), cert. denied,

549 U.S. 1186 (2007)............................................................ 19

United States v. Sanchez-Badillo,

540 F.3d 24 (1st Cir. 2008), cert. denied,

555 U.S. 1121 (2009)............................................................ 17

United States v. Sexton,

512 F.3d 326 (6th Cir.), cert. denied,

555 U.S. 928 (2008).............................................................. 17

United States v. Singh,

995 F.3d 1069 (9th Cir. 2021), cert. denied,

142 S. Ct. 1422 (2022) ......................................................... 20

United States v. Staten,

466 F.3d 708 (9th Cir. 2006) ............................................... 19

United States v. Vaughn,

430 F.3d 518 (2d Cir. 2005), cert. denied,

547 U.S. 1060 (2006)...................................................... 17, 19

United States v. Villareal-Amarillas,

562 F.3d 892 (8th Cir. 2009) ......................................... 17, 19

United States v. Watts, 519 U.S. 148 (1997) ................. 16, 18

Statutes, regulation, guideline, and rules:

Controlled Substances Act, 21 U.S.C. 801 et seq. ................. 9

21 U.S.C. 841(a) ......................................................... 11, 14

21 U.S.C. 841(a)(1)..................................................... 2, 5, 9

21 U.S.C. 841(b)(1)(C) ............................................... 2, 4, 5

21 U.S.C. 841(b)(2) .................................................... 2, 4, 5

21 U.S.C. 846 .................................................................. 2, 4

18 U.S.C. 2 ............................................................................ 2, 5

18 U.S.C. 3661 ........................................................................ 17

VI

Regulation, guideline, and rules—Continued:

Page

21 C.F.R. 1306.04(a) .................................................... 9, 10, 14

United States Sentencing Guidelines § 2D1.1 ...................... 6

Sup. Ct. R. 10 ......................................................................... 11

Fed. R. Evid:

Rule 702 ............................................................................ 12

Rule 702(a) ....................................................................... 13

Rule 704 ............................................................................ 12

Rule 704(a) ....................................................................... 13

Rule 704(b) ......................................................................... 8

In the Supreme Court of the United States

No. 21-1418

MEDARDO QUEG SANTOS, PETITIONER

v.

UNITED STATES OF AMERICA

ON PETITION FOR A WRIT OF CERTIORARI

TO THE UNITED STATES COURT OF APPEALS

FOR THE ELEVENTH CIRCUIT

BRIEF FOR THE UNITED STATES IN OPPOSITION

OPINIONS BELOW

The opinion of the court of appeals (Pet. App. 1a-27a)

is not published in the Federal Reporter but is available

at 2021 WL 6071511. The order of the district court (Pet.

App. 28a-39a) is unreported.

JURISDICTION

The judgment of the court of appeals was entered on

December 21, 2021. On March 15, 2022, Justice Thomas

extended the time within which to file a petition for a

writ of certiorari to and including April 20, 2022, and the

petition was filed on that date. The jurisdiction of this

Court is invoked under 28 U.S.C. 1254(1).

(1)

2

STATEMENT

Following a jury trial in the United States District

Court for the Middle District of Florida, petitioner was

convicted on one count of conspiring to unlawfully distribute oxycodone, hydromorphone, morphine, methadone, hydrocodone, and alprazolam, in violation of 21

U.S.C. 841(b)(1)(C), (b)(2), and 846; and three counts of

unlawfully distributing and dispensing combinations of

oxycodone, morphine, and alprazolam, in violation of 18

U.S.C. 2 and 21 U.S.C. 841(a)(1), (b)(1)(C), and (b)(2).

Judgment 1; see Pet. App. 2a, 33a. The court sentenced

petitioner to 72 months of imprisonment, to be followed

by three years of supervised release. Judgment 3-4.

The court of appeals affirmed. Pet. App. 1a-27a.

1. Petitioner was a licensed physician who served as

medical director at a pain-management clinic in Tampa,

Florida, that operated as a “pill mill” to “prescribe controlled substances regardless of whether its patients

ha[d] a medical need for them.” Pet. App. 1a-2a.

When petitioner interviewed for the medical director

position in 2014, the clinic’s owner “made it clear that

[clinic] patients expected to receive controlled substances during their visits” and informed petitioner

“about key aspects of the business model: very short,

timed patient appointments, high patient volume (30–40

patients per day), and cash only—no insurance payments.” Pet. App. 3a; see id. at 2a. “[C]haracteristics

of the clinic” likewise “suggested that it was not a legitimate medical operation.” Id. at 3a. For example, “the

clinic had barely any medical equipment—only an exam

table for the patients to sit on—or supplies.” Ibid.

Clinic staff who “had no medical or administrative training” handled patient intake and “wrote prescriptions for

controlled substances for the doctor to sign after each

3

patient’s brief visit.” Ibid. And the staff members’

“other duties included collecting cash payments from

patients and knocking on [petitioner’s] door to indicate

that the ten-minute appointment should end.” Ibid.

The clinic’s “patients exhibited recognizable signs of

drug-seeking behavior and drug addiction.” Pet. App.

3a. Many patients “ha[d] bloodshot eyes, slurr[ed]

their words, look[ed] sleepy, and stumbl[ed] when

they walked.” Id. at 3a-4a. “Some of them had visible

track marks, indicating intravenous drug abuse,” and

“[o]thers looked like they were going through opiate

withdrawal—sweating, shaking, vomiting, and experiencing hot and cold flashes.” Id. at 4a. Patients

“ ‘nodd[ed] out’ in the waiting room and ‘sho[t] up’ ” in

the parking lot, leaving behind “baggies, blunt wrappers, and syringes.” Ibid. (citation omitted). “[A]s

many as one in five patients tested positive for illegal

drugs during their drug tests,” which the clinic would

“administer[] * * * to pass state inspections,” unless

the patient “bribed [clinic] staff to skip” the test and

“falsif [y]” the results. Ibid. But “patients always left”

the clinic “with new prescriptions for controlled substances.” Ibid.

Petitioner’s behavior at the clinic “failed to comport

with usual professional practice.” Pet. App. 4a. He “saw

[patients] in brief appointments, timed by [clinic] staff,”

during which he often gave only “ ‘cursory physical examinations.’ ” Id. at 5a, 17a (citation omitted). He prescribed controlled substances even when “his patient’s

medical history or drug test was missing” and even

after “a patient told him she shared her pills with

friends or family.” Id. at 5a. And he “prescribed drugs

in * * * dangerous combinations.” Ibid. His conduct

4

also included prescribing controlled substances to “people who looked like drug users.” Ibid. And petitioner

“went on vacations but left prewritten, postdated prescriptions for his patients” to obtain in his absence.

Ibid.

On three occasions petitioner prescribed controlled

substances to an undercover Drug Enforcement Agency

(DEA) agent, Kathy Chin, who posed as a patient, and

a confidential informant, Robert Vasilas, who was a returning patient posing as Chin’s boyfriend. Pet. App.

5a-6a. At the first visit, petitioner saw the two together;

Vasilas stated that Chin had “ ‘robb[ed]’ him of his pills

when she ran out of hers.” Id. at 5a (citation omitted).

“Instead of investigating th[at] red flag, [petitioner]

gave them prescriptions for greater quantities of oxycodone.” Ibid. He also wrote Vasilas a Xanax (alprazolam) prescription without obtaining his relevant medical history, discussing tools to manage his putative condition, or suggesting alternative treatments. Id. at 5a6a. At the second visit, which only Chin attended, petitioner wrote prescriptions for Vasilas, gave them to

Chin, and made her “pay for a visit for Vasilas” although

he was not actually present. Id. at 6a. Petitioner also

“fill[ed] out Vasilas’s file as though he had examined

him.” Ibid. At the third visit, Vasilas stated that he had

run out of his pills and had obtained medications from

friends and family. Ibid. Petitioner “responded by giving Vasilas extra prescriptions” and charging him for

them. Ibid.

2. In 2017, a federal grand jury returned a superseding indictment charging petitioner with one count of

conspiring to unlawfully distribute oxycodone, hydromorphone, morphine, methadone, hydrocodone, and

alprazolam, all controlled substances, in violation of 21

5

U.S.C. 841(b)(1)(C), (b)(2), and 846; and five counts of

unlawfully distributing and dispensing various combinations of those controlled substances, in violation of 18

U.S.C. 2 and 21 U.S.C. 841(a)(1), (b)(1)(C), and (b)(2).

D. Ct. Doc. 38, at 2-6 (Oct. 3, 2017). The grand jury also

charged the clinic’s owner, a clinic executive, and another clinic physician with related offenses. Id. at 1-2.

Petitioner and the other physician proceeded to trial.

a. At trial, the clinic’s owner, patients and employees of the clinic, and government agents testified regarding petitioner’s prescribing conduct and clinical

practices. Pet. App. 6a; see pp. 2-4, supra. Petitioner

himself admitted “to treating patients who presented

with red flags, like obtaining medications from illegitimate sources, obtaining medications earlier than the

medically appropriate 30-day period, or traveling long

distances.” Pet. App. 36a-37a (citations omitted). And

the government’s expert witness, who was a licensed

physician and pain-management specialist, provided

“background testimony” on appropriate prescribing

practices based on standards outlined in a “DEA manual, state and federal regulations, and his own pain management practice,” id. at 23a; compared petitioner’s

prescribing practices to legitimate ones, id. at 23a-24a;

and testified that “ ‘most of ’ the prescriptions that [petitioner] wrote for controlled substances ‘were provided

for no legitimate medical purpose, and * * * not issued

in the course of [his] professional practice,’ ” id. at 7a

(brackets and citation omitted).

At the close of trial, the district court instructed the

jury that, in order to return a guilty verdict on the

counts for unlawfully dispensing a controlled substance,

it was required to find that (1) petitioner “distributed,

dispensed, and caused to be distributed and dispensed,

6

the controlled substance(s) as charged,” and (2) “at the

time of the distribution and dispensing, [petitioner]

knew that he was distributing and dispensing a controlled substance not for a legitimate medical purpose

and not in the usual course of professional practice.”

D. Ct. Doc. 337, at 20 (May 23, 2019). The court further

instructed the jury that

[w]hether [petitioner] acted outside the usual course

of professional practice is to be judged objectively by

reference to standards of medical practice generally

recognized and accepted in the United States, including the State of Florida. However, whether [petitioner] acted without a legitimate medical purpose

depends on [his] subjective belief whether he was

distributing the controlled substance for a legitimate

medical purpose. Therefore, in order for the Government to establish that [petitioner] was acting

without a legitimate medical purpose, the Government must prove beyond a reasonable doubt that

[he] did not subjectively believe that he was acting

with a good faith belief that he was distributing the

controlled substance for a legitimate medical purpose.

Id. at 20-21.

The jury found petitioner guilty on the conspiracy

charge and three distribution charges, acquitting him

on the other two distribution charges. Pet. App. 7a.

The district court denied petitioner’s post-verdict motion for acquittal or for a new trial. Id. at 28a-39a.

b. Before sentencing, the Probation Office determined that, pursuant to Sentencing Guidelines § 2D1.1,

petitioner’s base offense level was 38, based on the total

drug quantity involved in 86 of the clinic’s patient files.

Presentence Investigation Report ¶¶ 40, 63, 72-73. The

7

government subsequently determined that the relevant

drug quantity should be derived from a subset of those

patient files, resulting in a base offense level of 32.

D. Ct. Doc. 425, at 9-10 (Mar. 5, 2020). Petitioner agreed

that, “by a preponderance of the evidence * * * the drug

weight equates to a base offense level of 32,” id. at 10

n.4, but argued that the appropriate standard of proof

should be clear and convincing evidence, which would

result in a base offense level of six, D. Ct. Doc. 430, at

8-11 (Mar. 5, 2020).

At sentencing, the district court found the government’s recommended drug quantity by a preponderance of the evidence, calculated petitioner’s base offense level at 32, and set his advisory Guidelines range

at 151 to 188 months. 9/16/20 Tr. 33-34. The court imposed a below-Guidelines sentence of 72 months of imprisonment, to be followed by three years of supervised

release. Id. at 70.

3. The court of appeals affirmed in an unpublished

per curiam opinion. Pet. App. 1a-27a.

The court of appeals found, inter alia, “sufficient evidence to support the jury’s finding that [petitioner]

knowingly joined an agreement to unlawfully dispense

controlled substances.” Pet. App. 16a. And it rejected

petitioner’s claim, raised for the first time on appeal,

that the district court erred in allowing the government’s expert to testify that petitioner’s prescriptions

lacked a legitimate medical purpose and were not issued

in the usual course of professional practice. Id. at 21a25a.

The court of appeals observed that “[t]o convict a

doctor for violating 21 U.S.C. § 841(a), the government

must prove that she issued prescriptions with no legitimate medical purpose or outside of the usual course of

8

professional practice.” Pet. App. 21a. The court further

observed that “[t]he government often uses the testimony of a medical expert witness to satisfy its burden,”

as it did at petitioner’s trial. Id. at 21a-22a. And the

court emphasized that although an “expert witness can

give his opinion about an ultimate issue,” he “ ‘must not

state an opinion about whether the defendant did or did

not have a mental state or condition that constitutes an

element of the crime charged or of a defense,’ ” “giv[e]

legal opinions,” or “tell the jury what result to reach.”

Id. at 22a (quoting Fed. R. Evid. 704(b)).

After reviewing the trial record, the court of appeals

found that because the government’s expert “testified

about [petitioner’s] conduct and his professional opinion

of that conduct” and “did not speculate about what was

going on in [petitioner’s] mind,” he did not violate Federal Rule of Evidence 704(b). Pet. App. 23a. In addition, citing circuit precedent, the court found no plain

error in the district court’s admission of expert “testimony [that] reached the ultimate issue of whether [petitioner] prescribed drugs for no legitimate medical

purpose and outside the usual course of professional

practice.” Id. at 23a, 25a (citing United States v. Azmat,

805 F.3d 1018, 1036 (11th Cir. 2015), cert. denied, 578

U.S. 979 (2016)).

The court of appeals also rejected petitioner’s contention that the district court should have calculated

the total drug quantity using a clear-and-convincingevidence standard. Pet. App. 26a-27a. The court of appeals noted that it had “consistently held that district

courts are required to make factual findings for sentencing purposes by a preponderance of the evidence.”

Id. at 27a (citing United States v. Aguilar-Ibarra, 740

F.3d 587, 592 (11th Cir. 2014) (per curiam)).

9

ARGUMENT

Petitioner suggests (Pet. 16, 21-22) that the Court

could grant the petition for a writ of certiorari, vacate

the decision below, and remand the case for further consideration in light of Ruan v. United States, 142 S. Ct.

2370 (2022). But the jury instructions in petitioner’s

case comported with the Court’s holding in Ruan because they required the jury to find that petitioner subjectively believed that he was distributing controlled

substances not for a legitimate medical purpose before

finding him guilty of unlawful drug distribution. Petitioner also renews his contentions (Pet. 17-27) that the

district court erred both in its admission of the government expert’s testimony and in its application of a

preponderance-of-the-evidence standard when finding

facts to determine the applicable Guidelines range. The

court of appeals correctly rejected those contentions,

and its decision does not conflict with any decision of

this Court or implicate a circuit conflict that warrants

this Court’s intervention. The petition for a writ of certiorari should be denied.

1. Petitioner briefly suggests (Pet. 16) that the result in Ruan (which was not decided at the time that the

petition was filed) may cast doubt on his jury instructions. It does not.

The Controlled Substances Act (CSA or Act), 21

U.S.C. 801 et seq., makes it a federal crime “for any person knowingly or intentionally * * * to manufacture,

distribute, or dispense * * * a controlled substance,”

“[e]xcept as authorized” by the Act. 21 U.S.C. 841(a)(1).

A prescription is “authorized” by the Act when a licensed practitioner issues it “for a legitimate medical

purpose * * * acting in the usual course of his professional practice.” 21 C.F.R. 1306.04(a). In Ruan, this

10

Court held that the CSA’s “ ‘knowingly or intentionally’

mens rea applies to authorization.” 142 S. Ct. at 2375.

Accordingly, “[a]fter a defendant produces evidence

that he or she was authorized to dispense controlled

substances, the Government must prove beyond a reasonable doubt that the defendant knew that he or she

was acting in an unauthorized manner, or intended to

do so.” Ibid.

The jury instructions in this case were fully consistent with the Court’s decision in Ruan. They required the jury to find that, “at the time of the distribution and dispensing, [petitioner] knew that he was distributing and dispensing a controlled substance not for

a legitimate medical purpose and not in the usual course

of professional practice.” D. Ct. Doc. 337, at 20 (emphasis added). And in accord with Ruan’s recognition that

“the regulation defining the scope of a doctor’s prescribing authority does so by reference to objective criteria

such as ‘legitimate medical purpose’ and ‘usual course’

of ‘professional practice,’ ” 142 S. Ct. at 2382 (quoting 21

C.F.R. 1306.04(a)), the district court explained that the

phrase “usual course of professional practice” itself “is

to be judged objectively by reference to standards of

medical practice generally recognized and accepted

in the United States, including the State of Florida,”

D. Ct. Doc. 337, at 20.

The district court further instructed the jury that

whether petitioner “acted without a legitimate medical

purpose depends on [petitioner’s] subjective belief

whether he was distributing the controlled substance

for a legitimate medical purpose.” D. Ct. Doc. 337, at

20-21. “Therefore,” the court continued, “in order for

the Government to establish that [petitioner] was acting

without a legitimate medical purpose, the Government

11

must prove beyond a reasonable doubt that [he] did not

subjectively believe that he was acting with a good faith

belief that he was distributing the controlled substance

for a legitimate medical purpose.” Id. at 21.

Because the instructions here, inter alia, directed

the jury to determine whether petitioner “subjectively

believe[d]” that he had prescribed controlled substances for a legitimate medical purpose, D. Ct. Doc.

337, at 21, the jury necessarily found that he “knowingly

or intentionally acted in an unauthorized manner,”

when it convicted him of the Section 841(a) offenses,

Ruan, 142 S. Ct. at 2376. And because those instructions are consistent with the Court’s decision in Ruan,

they provide no basis for the Court to grant the petition,

vacate the judgment below, and remand for further proceedings in light of Ruan.

2. Petitioner principally contends (Pet. 16-23) that

the government’s expert improperly commented on petitioner’s state of mind and provided legal opinions during his testimony. Because petitioner did raise those

objections at trial, the court of appeals reviewed those

arguments for plain error, Pet. App. 22a-23a, 25a, which

requires petitioner to show “an error or defect” that

was “clear or obvious,” that “affected [petitioner’s] substantial rights,” and that “ ‘seriously affects the fairness, integrity or public reputation of judicial proceedings,’ ” Puckett v. United States, 556 U.S. 129, 135 (2009)

(brackets and citation omitted). The court’s factbound

determination that petitioner failed to satisfy those prerequisites is correct, and its unpublished decision does

not conflict with any authority from this Court or another court of appeals. Petitioner’s challenges to the

particular expert testimony in his case accordingly do

not warrant this Court’s review. See Sup. Ct. R. 10 (“A

12

petition for a writ of certiorari is rarely granted when

the asserted error consists of erroneous factual findings

or the misapplication of a properly stated rule of law.”);

United States v. Johnston, 268 U.S. 220, 227 (1925)

(“We do not grant * * * certiorari to review evidence

and discuss specific facts.”).

a. The admissibility of expert testimony is governed

by Rule 702, which provides that a qualified expert witness may testify if “scientific, technical, or other specialized knowledge will help the trier of fact to understand the evidence or to determine a fact in issue” and

if (1) “the testimony is based on sufficient facts or data”;

(2) “the testimony is the product of reliable principles

and methods”; and (3) “the expert has reliably applied

the principles and methods to the facts of the case.”

Fed. R. Evid. 702. Although an expert witness in a

criminal case “must not state an opinion about whether

the defendant did or did not have a mental state or

condition that constitutes an element of the crime

charged,” an expert opinion “is not objectionable just

because it embraces an ultimate issue.” Fed. R. Evid.

704. And a trial court has “broad latitude” in determining whether to admit or exclude expert testimony based

on “the particular circumstances of the particular case

at issue.” Kumho Tire Co. v. Carmichael, 526 U.S. 137,

142, 150 (1999).

The court of appeals correctly applied those principles in this case. At trial, the government’s expert provided “background testimony” regarding the use of controlled substances for legitimate medical purposes in

the usual course of professional practice based on

standards outlined in a “DEA manual, state and federal

regulations, and his own pain management practice.”

Pet. App. 23a; see id. at 23a-24a. And based on evidence

13

about petitioner’s conduct with the undercover DEA

agent and others, the expert “gave his opinion” that

petitioner “prescribed [the patients] controlled substances for no legitimate medical purpose and outside

the scope of professional practice.” Id. at 24a; see, e.g.,

id. at 7a.

The court of appeals correctly found that the district

court did not plainly err in admitting that testimony.

The expert’s opinion that petitioner prescribed controlled substances for no legitimate medical purpose

outside the scope of professional practice “is not objectionable just because it embraces an ultimate issue.”

Fed. R. Evid. 704(a). And because the expert’s “specialized knowledge * * * help[ed] the trier of fact to understand the evidence or to determine a fact in issue,”

Fed. R. Evid. 702(a)—generally accepted practices for

controlled-substance prescriptions—his testimony was

admissible.

Petitioner errs in asserting (Pet. 20) that the expert’s testimony “was riddled with inadmissible stateof-mind and legal opinions.” As the court of appeals

found after reviewing the record, the expert “testified

about [petitioner’s] conduct and his professional opinion

of that conduct, but he did not speculate about what was

going on in [petitioner’s] mind,” Pet. App. 23a, and petitioner identifies no instance of such state-of-mind testimony. Nor did the expert provide a “legal definition”

of the phrase “ ‘legitimate medical purpose,’ ” Pet. 20; instead, he testified about appropriate medical practices

based on his specialized knowledge of federal and state

controlled-substances regulations and guidance, as well

as his professional experiences, Pet. App. 23a-25a. That

was permissible because there is “no [federal] interpre-

14

tive rule seeking to define a practice as lacking any legitimate medical purpose.” United States v. Lovern,

590 F.3d 1095, 1100 (10th Cir. 2009) (Gorsuch, J.). The

government thus typically establishes the content of

“usual course of professional practice the old-fashioned

way: through witnesses and documentary proof at trial

focused on the contemporary norms of the medical profession.” Ibid. The government’s expert here did just

that, and “the jury * * * remained free to sort out all

the competing proof ” on “what constitutes usual medical practice.” Ibid.

Petitioner also errs in asserting (Pet. 22) that the

government’s expert improperly treated the concepts of

“legitimate medical purpose” and “usual course of professional practice” as “objective” standards. As this

Court observed in Ruan, “the regulation defining the

scope of a doctor’s prescribing authority does so by reference to objective criteria such as ‘legitimate medical

purpose’ and ‘usual course’ of ‘professional practice.’ ”

142 S. Ct. at 2382 (quoting 21 C.F.R. 1306.04(a)) (emphasis added). And the objective bounds of those standards are relevant in Section 841(a) prosecutions; as this

Court explained in Ruan, “ ‘the more unreasonable’ a

defendant’s ‘asserted beliefs or misunderstandings are,’

especially as measured against objective criteria, ‘the

more likely the jury . . . will find that the Government

has carried its burden of proving knowledge.’ ” Ibid.

(quoting Cheek v. United States, 498 U.S. 192, 203-204

(1991)).

b. Even assuming that the district court erred in admitting portions of the expert’s testimony, petitioner

cannot prevail on the third element of the plain-error

test, which requires him to show that the alleged error

prejudiced his substantial rights. See Puckett, 556 U.S.

15

at 135. He cannot make that showing because he cannot

establish “a ‘reasonable probability’ that he would have

been acquitted” had the court excluded the government’s expert. Greer v. United States, 141 S. Ct. 2090,

2097 (2021) (citation omitted).

At trial, the clinic’s owner, patients and employees of

the clinic, government agents, and petitioner himself

testified regarding the problematic nature of petitioner’s prescribing conduct and clinical practices—

including various characteristics that indicated that the

clinic “was not a legitimate medical operation.” Pet.

App. 3a; see pp. 2-4, supra. And petitioner’s own expert, a pain-management doctor, provided evidence that

matched the government expert’s. For example, he testified that it was a red flag if a patient traveled a long

distance to obtain controlled substances, obtained medication from friends or family members, or presented

with inconsistent drug test results—all of which are fact

patterns petitioner saw but ignored. 5/21/19 Tr. 84, 8790.

Petitioner offers no reason to conclude that—despite

that evidence—his prescriptions reflected a legitimate

medical purpose in the usual course of professional

practice. This Court has already recognized that similar conduct—such as “g[iving] inadequate physical examinations,” “t[aking] no precautions against * * *

misuse and diversion,” and charging a “fee according to

the number of tablets desired”—“exceed[s] the bounds

of ‘professional practice.’ ” United States v. Moore, 423

U.S. 122, 142-143 (1975). Thus, even assuming arguendo that admission of all or part of the expert testimony offered by the government was erroneous, petitioner cannot show a reasonable probability that he

16

would have been acquitted, and accordingly can show no

plain error.

3. Finally, petitioner contends (Pet. 23, 25) that the

district court “should have calculated [the] drug weight

under a clear-and-convincing evidence standard” and

that this Court’s review is warranted to resolve a circuit

conflict about the proper factfinding standard for sentencing facts that “dramatically increase a sentence.”

The courts below correctly rejected that argument.

This Court has repeatedly and recently declined to review claims similar to the one petitioner raises. See,

e.g., McCray v. United States, 142 S. Ct. 1373 (2022)

(No. 21-6077); Parlor v. United States, 142 S. Ct. 623

(2021) (No. 21-6148); Idelfonso v. United States, 139

S. Ct. 178 (2018) (No. 17-9470); Siegelman v. United

States, 577 U.S. 1092 (2016) (No. 15-353); O’Bryant v.

United States, 577 U.S. 987 (2015) (No. 15-5171); Chandia v. United States, 568 U.S. 1011 (2012) (No. 12-5093);

Butler v. United States, 565 U.S. 1063 (2011) (No. 115952); Lee v. United States, 565 U.S. 829 (2011) (No. 109512); Culberson v. United States, 562 U.S. 1289 (2011)

(No. 10-7097); Gibson v. United States, 559 U.S. 906

(2010) (No. 09-6907). It should follow the same course

here.

a. As this Court observed in United States v. Watts,

519 U.S. 148 (1997) (per curiam), it has “held that [a sentencing court’s] application of the preponderance standard at sentencing” to find facts that inform the court’s

selection of a sentence within the prescribed statutory

range “generally satisfies due process.” Id. at 156; see

Alleyne v. United States, 570 U.S. 99, 116 (2013)

(“[B]road sentencing discretion, informed by judicial

factfinding, does not violate the Sixth Amendment.”);

United States v. Booker, 543 U.S. 220, 233 (2005)

17

(“[W]hen a trial judge exercises his discretion to select

a specific sentence within a defined range, the defendant has no right to a jury determination of the facts that

the judge deems relevant.”); see also 18 U.S.C. 3661

(“No limitation shall be placed on the information concerning the background, character, and conduct of a

person convicted of an offense which a court of the

United States may receive and consider for the purpose

of imposing an appropriate sentence.”).

Consistent with Watts, the courts of appeals have

uniformly recognized that a sentencing judge may generally find facts relevant to the determination of the

sentencing range under the advisory federal Guidelines

by a preponderance of the evidence, so long as the judge

imposes a sentence within the statutory range. See,

e.g., United States v. Culver, 598 F.3d 740, 752-753 (11th

Cir.), cert. denied, 562 U.S. 896 (2010); United States

v. Grubbs, 585 F.3d 793, 803 (4th Cir. 2009), cert.

denied, 559 U.S. 1022 (2010); United States v. VillarealAmarillas, 562 F.3d 892, 897-898 (8th Cir. 2009); United

States v. Sanchez-Badillo, 540 F.3d 24, 34 (1st Cir.

2008), cert. denied, 555 U.S. 1121 (2009); United States

v. Sexton, 512 F.3d 326, 329-330 (6th Cir.), cert. denied,

555 U.S. 928 (2008); United States v. Bras, 483 F.3d 103,

107-108 (D.C. Cir. 2007); United States v. Grier, 475

F.3d 556, 568 (3d Cir.) (en banc), cert. denied, 552 U.S.

848 (2007); United States v. Kilby, 443 F.3d 1135, 11401141 (9th Cir. 2006); United States v. Garcia, 439 F.3d

363, 369 (7th Cir. 2006); United States v. Vaughn, 430

F.3d 518, 525 (2d Cir. 2005), cert. denied, 547 U.S. 1060

(2006); United States v. Magallanez, 408 F.3d 672, 684685 (10th Cir.), cert. denied, 546 U.S. 955 (2005); United

States v. Mares, 402 F.3d 511, 519 (5th Cir.), cert. denied, 546 U.S. 828 (2005).

18

b. The district court’s determination of petitioner’s

sentence, based in part on its finding the applicable

drug quantity by a preponderance of the evidence, is

consistent with that uniform authority.

As petitioner notes (Pet. 25), before this Court’s decision in United States v. Booker, supra, “a divergence

of opinion [existed] among the Circuits as to whether, in

extreme circumstances, relevant conduct that would

dramatically increase the sentence must be based on

clear and convincing evidence.” Watts, 519 U.S. at 156.

But after the Court held that the Guidelines are advisory in Booker, 543 U.S. at 245, the courts of appeals

have clarified that a sentencing judge may find facts

that increase a defendant’s sentence by a preponderance of the evidence, provided that the sentence remains within the statutory range.

For example, the Third Circuit’s pre-Booker decision

in United States v. Kikumura, 918 F.2d 1084 (1990), had

suggested—without deciding—that due process might

require using a clear-and-convincing standard of proof

to find sentencing factors in some exceptional cases.

See id. at 1102. The Third Circuit has since expressly

repudiated that suggestion, recognizing that Booker obviated any prior doubts about sentencing judges’ ability

to “find facts by a preponderance of the evidence, provided that the sentence actually imposed is within the

statutory range, and is reasonable.” United States v.

Fisher, 502 F.3d 293, 305 (2007), cert. denied, 552 U.S.

1274 (2008).

Other courts of appeals likewise have recognized

that the “debate has * * * been rendered academic” by

Booker, for “[w]ith the guidelines no longer binding the

sentencing judge, there is no need for courts of appeals

to add epicycles to an already complex set of (merely)

19

advisory guidelines by multiplying standards of proof.”

United States v. Reuter, 463 F.3d 792, 793 (7th Cir.

2006), cert. denied, 549 U.S. 1186 (2007); see, e.g.,

Grubbs, 585 F.3d at 801 (“Whatever theoretical validity

may have attached to [an] exception to a preponderance

of the evidence sentencing standard, the Supreme

Court’s decision in Booker and subsequent cases applying Booker have nullified its viability.”); VillarealAmarillas, 562 F.3d at 897 (“[D]ue process never requires applying the clear and convincing evidence

standard to judicial fact-finding at criminal sentencing.”); United States v. Brika, 487 F.3d 450, 462 (6th

Cir.) (“[W ]e reaffirm our earlier holding that due process does not require sentencing courts to employ a

standard higher than preponderance-of-the-evidence,

even in cases dealing with large enhancements.”), cert.

denied, 552 U.S. 938 (2007); Vaughn, 430 F.3d at 525

(Sotomayor, J.) (“We reiterate that, after Booker, district courts’ authority to determine sentencing factors

by a preponderance of the evidence endures and does

not violate the Due Process Clause of the Fifth Amendment.”).

The only exception is the Ninth Circuit, whose decision in United States v. Staten, 466 F.3d 708 (2006), adhered to its pre-Booker rule that “when a sentencing

factor has an extremely disproportionate effect on the

sentence relative to the conviction, the government

must prove such a factor by clear and convincing evidence.” Id. at 717 (citation omitted); see United States

v. Parlor, 2 F.4th 807, 816-817 (9th Cir.), cert. denied,

142 S. Ct. 623 (2021). Staten’s endorsement of the clearand-convincing standard of proof, however, “trace[d]

back to,” and relied heavily on, the Third Circuit’s decision in Kikumura. Staten, 466 F.3d at 719; see id. at

20

719-720. The Third Circuit has since overridden that

decision, explaining that any suggestion in Kikumura

that due process requires a heightened standard of

proof “was predicated on the then-mandatory nature of

the Guidelines” and “does not survive Booker.” Fisher,

502 F.3d at 305-306. The full Ninth Circuit might well

decide in the future to likewise realign with other circuits. See United States v. Singh, 995 F.3d 1069, 1081

(9th Cir. 2021) (declining invitation to revisit Staten to

decide whether “the preponderance of the evidence

standard should apply * * * once the Guidelines became permissive” because “the record support[ed] the

application of the enhancement under either standard

of proof ”), cert. denied, 142 S. Ct. 1422 (2022); see also

United States v. Buchan, No. 19-50272, 2021 WL

4988020, at *1 (9th Cir. Oct. 27, 2021) (R. Nelson, J.,

concurring) (“[T]he clear and convincing evidence rule

should be reversed en banc because it is incorrect, unmoored from its original basis in the mandatory nature

of the Guidelines, and contrary to the law of every other

circuit.”).

The sentencing question presented by the petition

accordingly continues not to warrant this Court’s review, and the Court should deny the petition as it has

repeatedly done with similar petitions. See p. 16, supra.

Indeed, this case—which involves a substantially belowGuidelines sentence, see 9/16/20 Tr. 34, 70—would be an

especially unsuitable vehicle for reviewing the issue.

21

CONCLUSION

The petition for a writ of certiorari should be denied.

Respectfully submitted.

ELIZABETH B. PRELOGAR

Solicitor General

KENNETH A. POLITE, JR.

Assistant Attorney General

DAVID M. LIEBERMAN

Attorney

SEPTEMBER 2022