USA v. Kendrick Eugene Duldulao, et al.

[DO NOT PUBLISH]
In the
United States Court of Appeals
For the Eleventh Circuit
____________________
No. 20-13973
____________________
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
versus
KENDRICK EUGENE DULDULAO,
MEDARDO QUEG SANTOS,
Defendants-Appellants.
____________________
Appeals from the United States District Court
for the Middle District of Florida
D.C. Docket No. 8:17-cr-00420-MSS-AEP-4
____________________
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2 Opinion of the Court 20-13973
Before J ORDAN, J ILL PRYOR , and TJOFLAT, Circuit Judges.
PER CURIAM:
Kendrick Eugene Duldulao and Medardo Queg Santos,
both physicians, served sequentially as Medical Directors of a pain
management clinic in Tampa, Florida, called Health and Pain
Clinic (“HPC”). HPC liberally dispensed controlled substances to
its patients. Duldulao and Santos, along with others involved with
HPC, were charged with drug and conspiracy crimes related to
their activities at the clinic. A jury convicted Duldulao and Santos;
they now appeal the sufficiency of the evidence supporting their
conspiracy convictions, and Santos appeals the district court’s
admittance of expert testimony, as well as his sentence. After
careful review, and with the benefit of oral argument, we affirm.
I. BACKGROUND1
A superseding indictment charged Duldulao and Santos
with one count of conspiracy to distribute and dispense oxyco-
done, hydromorphone, morphine, methadone, and hydrocodone
(Schedule II controlled substances) and alprazolam (Xanax, a
Schedule IV controlled substance), not for a legitimate medical
purpose and not in the usual course of professional practice, in
violation of 21 U.S.C. § 846. It also charged both men with sub-
1 Because we write for the parties, we recount only the facts necessary to ex-
plain our decision.
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20-13973 Opinion of the Court 3
stantive counts of distributing controlled substances not for a le-
gitimate medical purpose and not in the usual course of profes-
sional practice, in violation of 21 U.S.C. § 841.
Ernest Gonzalez, the de facto owner of HPC, hired
Duldulao in 2011 and Santos in 2014 to work at his pill mill. A pill
mill is a pain management clinic that does not follow medical
standards because its purpose is to prescribe controlled substances
regardless of whether its patients have a medical need for them. A
hallmark of the pill mill is that procedures to ensure patients re-
ceived prescriptions only for legitimate medical needs are non-
existent or frequently not followed. To that end, HPC’s proce-
dures ensured that patients got into the doctor’s office and out
with their prescriptions as quickly as possible. Although the clinic
was not supposed to dole out controlled substances to patients
who were abusing the drugs, its patients exhibited recognizable
signs of drug-seeking behavior and drug addiction.
Gonzalez knew that the patients “were coming in [] to get
controlled substances,” so, at Duldulao’s and Santos’s respective
job interviews, Gonzalez made it clear that HPC’s patients ex-
pected to receive controlled substances during their visits. Doc.
382 at 38.2 Gonzalez confirmed that Duldalao knew the clinic was
“needing a doctor who was going to do controlled substances”
and discussed specific controlled substances that Duldulao would
2 “Doc.” numbers are the district court’s docket entries.
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4 Opinion of the Court 20-13973
use to treat the clinic’s patients. Doc. 382 at 36. Gonzalez also told
Duldulao and Santos 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.
Aside from what Duldulao and Santos were told during
their interviews, characteristics of the clinic suggested that it was
not a legitimate medical operation. For example, the clinic had
barely any medical equipment—only an exam table for the pa-
tients to sit on—or supplies.
As another example, the HPC staff who ran the front desk
and did patient intake had no medical or administrative training.
Yet they wrote prescriptions for controlled substances for the doc-
tor to sign after each patient’s brief visit. Their other duties in-
cluded collecting cash payments from patients and knocking on
the doctor’s door to indicate that the ten-minute appointment
should end.
What is more, many of the patients appeared to be drug
abusers. Witnesses described them as having bloodshot eyes, slur-
ring their words, looking sleepy, and stumbling when they
walked. Some of them had visible track marks, indicating intrave-
nous drug abuse. Others looked like they were going through
opiate withdrawal—sweating, shaking, vomiting, and experienc-
ing hot and cold flashes. People were “nodding out” in the wait-
ing room and “shooting up” in the parking lot. Doc. 384 at 100;
Doc. 387 at 42. Patients hung out in the parking lot and left be-
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20-13973 Opinion of the Court 5
hind trash like baggies, blunt wrappers, and syringes. Appearances
aside, as many as one in five patients tested positive for illegal
drugs during their drug tests at HPC. The clinic administered
drug tests to pass state inspections, but patients sometimes bribed
HPC staff to skip the drug test. The staff falsified test records after
letting patients skip the test.
Nevertheless, according to witnesses, HPC patients always
left with new prescriptions for controlled substances. To obtain
prescription medication, HPC patients did not need much docu-
mentation of a condition that required pain management—just an
MRI within the last two years documenting a physical abnormali-
ty of some kind. That and a Florida driver’s license got the pa-
tients prescriptions for controlled substances like oxycodone and
methadone.
Furthermore, both defendants’ own practices failed to
comport with usual professional practice. During patient ap-
pointments, Duldulao conducted cursory medical examinations.
Sometimes he spent up to five minutes on the physical exam;
sometimes he simply did not perform one. He spent little time on
patient medical history. When he went on vacation, his patients
picked up prewritten, postdated prescriptions without any medi-
cal exam at all. He wrote prescriptions for controlled substances
for patients even when they bore visible track marks or had trav-
eled from long distances—both red flags for controlled substance
abuse, according to the government’s medical expert witness, Dr.
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6 Opinion of the Court 20-13973
Kevin Chaitoff. Duldulao prescribed controlled substances in
dangerous combinations, allowing his patients to mix Xanax,
methadone, and a muscle relaxer called Soma. He even admitted
to his girlfriend that he worked at a “pain mill.” Doc. 386 at 143.
When Santos replaced Duldulao as HPC’s Medical Direc-
tor, little changed at HPC. Like Duldulao had, Santos prescribed
controlled substances to people who looked like drug abusers. He
saw them in brief appointments, timed by HPC staff. It did not
matter if his patient’s medical history or drug test was missing. It
did not matter if a patient told him she shared her pills with
friends or family. He prescribed patients controlled substances
nonetheless. He prescribed drugs in the same dangerous combi-
nations that Duldulao had. Santos, too, went on vacations but left
prewritten, postdated prescriptions for his patients.
Unbeknownst to Santos, however, two of his patients were
government agents: undercover DEA task force member Kathy
Chin and her “boyfriend,” confidential informant Robert Vasilas.
Santos’s unlawful interactions with them led to his three substan-
tive convictions for unlawful distribution. Santos’s first substan-
tive conviction for distribution and dispensing arose out of the
first time Chin and Vasilas saw Santos together. Vasilas, a return-
ing patient, told Santos that Chin was “robbing” him of his pills
when she ran out of hers. Doc. 386 at 173. Instead of investigating
this red flag, Santos gave them prescriptions for greater quantities
of oxycodone. He also wrote Vasilas a new prescription for Xanax
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20-13973 Opinion of the Court 7
without asking him about his history with anxiety or what tools
he used to manage it. He started Vasilas on Xanax, when most
doctors would not have prescribed that drug to someone who
was also taking an opioid. At no point did Santos discuss alterna-
tive treatments or milder medications with either patient.
Santos’s second substantive conviction stemmed from a
visit Chin made to HPC without Vasilas. In an earlier visit, Santos
had agreed to give Chin prescriptions to take to Vasilas, who said
he was going to be out for town for work. Santos told Chin she
would have to pay for a visit for Vasilas, even though Vasilas
would not actually be present. Santos gave her prescriptions for
the absent Vasilas, even filling out Vasilas’s file as though he had
examined him.
The third substantive conviction concerned a return visit
by Chin and Vasilas. Vasilas told Santos that he had run out of his
pills and had been getting medications from friends and family.
Santos responded by giving Vasilas extra prescriptions with a “do
not fill until” date; Santos charged him for the prewritten pre-
scriptions. After collecting evidence through these undercover
visits, the government indicted Santos, Duldulao, and Gonzalez.
Gonzalez pled guilty and testified against Santos and Duldulao.
At trial, the government established the above facts
through the testimony of Gonzalez, government agents, HPC pa-
tients, and HPC employees. The government also called Dr.
Chaitoff, an expert in pain management treatment, to testify
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8 Opinion of the Court 20-13973
about how he practices pain management. Dr. Chaitoff testified
that in his practice he conducts a comprehensive physical exam
on patients; speaks with them about their medical history, their
current pain, and the narcotics agreement patients are required by
law to sign; and typically allots 30 to 35 minutes for an initial visit
and 20 minutes for a follow-up—much longer than the appoint-
ments patients received with Duldulao or Santos. He testified that
patients who are clearly abusing controlled substances should not
be treated with more controlled substances, even if they have a
legitimate pain problem.
Dr. Chaitoff opined that “most of” the prescriptions that
Santos wrote for controlled substances “were provided for no le-
gitimate medical purpose, [and] they were not issued in the
course of one’s professional practice.” Doc. 388 at 20. Santos
moved to strike his testimony, but the district court denied the
motion, noting that Santos could still effectively cross-examine
Chaitoff to challenge his credibility.
After the government rested its case, both Duldulao and
Santos moved for a judgment of acquittal. At the conclusion of
the trial, the district court granted Duldulao’s motion as to most
of the substantive counts of dispensing and distributing controlled
substances but otherwise denied the motions. The jury convicted
Duldulao of conspiracy and acquitted him of the one remaining
substantive count of dispensing and distributing controlled sub-
stances. The jury convicted Santos of conspiracy and three sub-
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20-13973 Opinion of the Court 9
stantive charges of distribution relating to his treatment of Chin
and Vasilas, but it acquitted him of two other charges of distribu-
tion. After the jury returned its verdict, Duldulao and Santos re-
newed their motions for judgment of acquittal the district court
denied their motions. The court ultimately sentenced Duldulao to
twelve months and one day of imprisonment and Santos to six
years of imprisonment.
On appeal, Duldulao and Santos now challenge their con-
victions, and Santos also challenges his sentence.
II. STANDARD OF REVIEW
We review the sufficiency of the evidence
de novo when,
as here, the defendants have preserved their claims by moving for
judgments of acquittal.
United States v. Azmat, 805 F.3d 1018,
1035 (11th Cir. 2015).
We review evidentiary issues that were not raised at trial
for plain error, which “occurs if (1) there was error, (2) that was
plain, (3) that affected the defendant’s substantial rights, and
(4) that seriously affected the fairness, integrity, or public reputa-
tion of judicial proceedings.”
United States v. Wright,
607 F.3d 708, 715 (11th Cir. 2010) (internal quotation marks omit-
ted). An error is plain if it is “clear” or “obvious.”
United States v.
Olano, 507 U.S. 725, 734 (1993). We have explained that “where
the explicit language of a statute or rule does not specifically re-
solve an issue, there can be no plain error where there is no prec-
edent from the Supreme Court or this Court directly resolving it.”
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10 Opinion of the Court 20-13973
United States v. Chau, 426 F.3d 1318, 1322 (11th Cir. 2005) (inter-
nal quotation marks omitted).
We review the district court’s denial of a motion to strike
testimony for an abuse of discretion.
See United States v. Ander-
son, 782 F.2d 908, 916 (11th Cir. 1986). We will reverse only if we
find an error that affected the defendant’s substantial rights.
See
United States v. Barton, 909 F.3d 1323, 1337 (11th Cir. 2018).
We review a district court’s application of the Sentencing
Guidelines
de novo.
United States v. Johnson, 980 F.3d 1364, 1374
(11th Cir. 2020).
III. DISCUSSION
Duldulao and Santos challenge their convictions on the
ground that there was insufficient evidence that they knowingly
agreed to participate in the pill mill conspiracy. Santos challenges
his conviction on the additional grounds that the district court
made two reversible trial errors. He contends that the court plain-
ly erred in admitting Dr. Chaitoff’s testimony about his treatment
of patients and that it abused its discretion in denying his motion
to strike Dr. Chaitoff’s testimony. Santos also appeals his sen-
tence, arguing that the district court should have applied a clear-
and-convincing-evidence standard, rather than a preponderance-
of-the-evidence standard, to any relevant conduct findings that
would increase his offense level. We address each issue in turn.
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20-13973 Opinion of the Court 11
A. The Defendants’ Challenges to the Sufficiency of the Evidence
Sufficiency of the evidence review requires us to examine
“whether the evidence, when viewed in the light most favorable
to the government, and accepting reasonable inferences and cred-
ibility choices by the fact-finder, would enable the trier of fact to
find the defendant guilty beyond a reasonable doubt.”
United
States v. Monroe, 866 F.2d 1357, 1365 (11th Cir. 1989). We will
affirm a conviction unless there is “no reasonable construction of
the evidence” from which the jury could have found the defend-
ant guilty beyond a reasonable doubt.
United States v. Garcia,
405 F.3d 1260, 1269 (11th Cir. 2005).
To establish conspiracy in violation of 21 U.S.C. § 846, the
government must prove beyond a reasonable doubt that “(1)
there was an agreement between two or more people to commit
a crime (in this case, unlawfully dispensing controlled substances
in violation of § 841(a)(1)); (2) the defendant knew about the
agreement; and (3) the defendant voluntarily joined the agree-
ment.”
Azmat, 805 F.3d at 1035. An unlawful distribution under
§ 841(a)(1) occurs in the medical context when “(1) the prescrip-
tion was not for a legitimate medical purpose or (2) the prescrip-
tion was not made in the usual course of professional practice.”
United States v. Abovyan, 988 F.3d 1288, 1305 (11th Cir. 2021).
“The rule is disjunctive, and a doctor violates the law if he falls
short of either requirement.”
Id.
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12 Opinion of the Court 20-13973
The government does not need direct evidence to prove
conspiracy; circumstantial evidence can prove each element. The
first element, the existence of an agreement, “may be proved by
inferences from the conduct of the alleged participants or from
circumstantial evidence of a scheme.”
Azmat, 805 F.3d at 1035 (in-
ternal quotation marks omitted). The second element, knowledge
of an agreement, will be satisfied if “the circumstances surround-
ing a person’s presence at the scene of conspiratorial activity are
so obvious that knowledge of its character can fairly be attributed
to him.”
Id. (internal quotation marks omitted). As for the third
element, that the defendant voluntarily joined in the agreement,
circumstantial evidence can show a defendant participated in a
conspiracy “by showing that he committed acts that furthered the
purpose of the conspiracy.”
United States v. Iriele, 977 F.3d 1155,
1172 (11th Cir. 2020). Our cases sometimes merge the first two
elements and abbreviate the elements of conspiracy as
“knowledge” and “participation.”
See, e.g.,
id. at 1169–73;
Azmat,
805 F.3d at 1036–37.
Circumstantial evidence of conspiracy includes “red flags”
that would have put a reasonable doctor on notice of the illegiti-
macy of the operation.
See, e.g.,
Azmat, 805 F.3d at 1036 (“All of
the witnesses with medical backgrounds also testified that there
was an abundance of red flags that should have tipped off any
doctor that his patients were seeking pills.”). Where, as here, the
defendant is a doctor who allegedly participated in a pill mill con-
spiracy, we have looked to evidence of the doctor’s interaction
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20-13973 Opinion of the Court 13
with patients to conclude “that a defendant distributed a prescrip-
tion without a legitimate medical purpose and outside the usual
course of professional practice.”
United States v. Joseph,
709 F.3d 1082, 1104 (11th Cir. 2013). These aspects include inordi-
nately large quantities of controlled substances prescribed, brief or
nonexistent physical examinations, failure to review patient histo-
ry before prescribing medications, issuance of prescriptions to a
patient known to be delivering the drugs to others, and a lack of a
logical relationship between the drugs prescribed and treatment
of the allegedly existing condition.
See id.;
Azmat, 805 F.3d at
1036.
There were sufficient red flags in evidence in this case to
establish the defendants’ knowledge of an unlawful scheme.
Combined with the evidence of the defendants’ own conduct,
there was sufficient evidence that Duldulao and Santos knowingly
joined an agreement to unlawfully dispense controlled substanc-
es.
1. Duldulao’s Sufficiency Challenge
Duldulao argues that there was insufficient evidence to
support the elements of the conspiracy charge and, specifically,
that the red-flag evidence was weak. We agree with the district
court that there was sufficient evidence for the jury to find that he
knowingly joined an agreement to unlawfully dispense controlled
substances. The district court relied on the following types of evi-
dence: HPC owner Ernest Gonzalez’s testimony that Duldulao
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14 Opinion of the Court 20-13973
agreed to write narcotics prescriptions; staff and patient testimony
about Duldulao’s adherence to the plan to write controlled sub-
stance prescriptions to the vast majority of the clinic’s clientele;
staff testimony regarding HPC’s operations while Duldulao
served as Medical Director; patient testimony that confirmed the
clinic’s standard operating scheme under Duldulao; and
Duldulao’s statements to his then-girlfriend Kelly Schleisner
about the clinic, including that it was a “pain mill.” Doc. 376 at 6–
9. This evidence was sufficient to establish that Duldulao know-
ingly and voluntarily joined an agreement to unlawfully distribute
controlled substances.
From this evidence, the jury reasonably could have found
that the government proved all three elements of the conspiracy
charge. As this Court has in other cases, here we treat the first and
second elements, an agreement to commit a crime and
knowledge of the agreement, as a single knowledge element. The
jury reasonably could have inferred that Duldulao had knowledge
of the criminal object of the conspiracy based on Gonzalez’s tes-
timony about his interview with Duldulao for the position of
Medical Director, HPC staff’s testimony about Duldulao’s con-
duct at the clinic, staff and patient testimony about the patients,
and Duldulao’s statements to Schleisner. For the third element,
voluntary participation, the jury reasonably could have concluded
from the testimony concerning his conduct and interactions with
patients that Duldulao willingly agreed to and did participate in
the conspiracy.
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20-13973 Opinion of the Court 15
First, we turn to the knowledge element. Gonzalez’s testi-
mony was evidence that Duldulao knew about the suspicious na-
ture of HPC from the beginning and nevertheless agreed to get
involved. During Duldulao’s job interview, Gonzalez showed him
a file that listed the types of controlled substances HPC had pre-
viously prescribed for patients. Gonzalez told Duldulao that pa-
tient visits were timed and that it was “expected that he would
probably take about ten minutes” for each patient. Doc. 382 at
40–41. To “expedite things,” the staff would write out prescrip-
tions before the patient’s visit that Duldulao could sign after-
wards.
Id. at 41–42. This is circumstantial evidence of a scheme to
get controlled substances into patients’ hands as quickly as possi-
ble without regard to medical need. This evidence could lead a
jury to conclude that Duldulao agreed to join the conspiracy
when he agreed to prescribe opiates under those conditions.
In addition to what he knew before accepting his position
as Medical Director of HPC, in treating his patients Duldulao
would have seen that they exhibited signs of drug addiction,
which are red flags for doctors.
See Iriele, 977 F.3d at 1170;
Az-
mat, 805 F.3d at 1036. Witnesses described patients as looking like
drug abusers—for example, they were “a little too sleepy,” slurred
their speech, had bloodshot eyes or dilated pupils, had visible
track marks, smelled of marijuana, and “nodd[ed] out” in the
waiting room. Doc. 382 at 92, 96. One employee testified that
some patients looked “like they were sleepy and like falling when
they would walk.” Doc. 382 at 155. Another described the waiting
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16 Opinion of the Court 20-13973
room as “[s]ometimes chaos” with “people nodding out.” Doc.
384 at 100. One witness testified that he was addicted to drugs
while he was a patient at HPC and looked like “death warmed
over.”
Id. at 257
. Nevertheless, he and others like him left
Duldulao’s office with prescriptions for opiates and other con-
trolled substances.
Beyond the patients’ appearances, Duldulao heard from
HPC staff that some patients had tested positive for illegal drugs.
Staff also told him that some patients traveled long distances to
reach the clinic, bypassing other pain management doctors and
spending hours in a car despite their supposed chronic pain.
Again, our precedent in
Azmat warns that these red flags suggest
the patients were seeking drugs without a legitimate medical pur-
pose. 805 F.3d at 1036. Yet Duldulao prescribed them those drugs.
A jury reasonably could infer that he knew the patients were like-
ly drug abusers and knew that he was participating in a conspiracy
to unlawfully prescribe them controlled substances.
Other circumstances surrounding Duldulao’s presence at
HPC are such that a jury reasonably could attribute knowledge of
the conspiracy’s unlawful character to him. Duldulao knew the
clinic’s parking lot was covered with trash, including drug para-
phernalia, and that the clinic had little medical supplies or equip-
ment. He knew the staff had no training for or experience with
working in a medical office, yet they pre-wrote prescriptions for
him to sign. He was also aware that HPC did not accept insur-
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20-13973 Opinion of the Court 17
ance: patients could only pay in cash. The jury could infer that he
had “knowledge of the conspiracy due to his presence at” the clin-
ic.
See id.
Second, the element of active participation in the conspira-
cy found support in the evidence of Duldulao’s conduct and in-
teractions with the patients. Some HPC patients testified that
Duldulao did not review their medical history forms and that his
physical exams were as brief as two minutes, if they happened at
all.
See id. Duldulao sometimes prescribed combinations of opi-
oids, Xanax, and Soma, drugs “described in the . . . medical litera-
ture as the unholy holy trinity for substance abuse.”
Iriele,
977 F.3d at 1170 (internal quotation marks omitted). When he
went on vacation, Duldulao signed prewritten and postdated pre-
scriptions and left them with HPC staff so patients could come in
to pick them up without a physician present or any medical exam.
See Joseph, 709 F.3d at 1090–91 (“[E]very ‘legitimate doctor’ . . .
knows that he may not pre-sign prescriptions.”). A jury could rea-
sonably infer from this conduct that Duldulao actively participat-
ed in the conspiracy.
Duldulao argues that this evidence was insufficient to sup-
port his conspiracy conviction. He points out that Gonzalez did
not testify to telling Duldulao that HPC was a pill mill, that the
job was contingent on Duldulao’s agreement to exclusively write
prescriptions for controlled substances, or that the patients would
not have a medical need for these drugs. And, as Duldulao em-
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18 Opinion of the Court 20-13973
phasized, Gonzalez testified that, despite his own guilty plea, he
was not guilty of conspiracy. testified that he “[n]ever” conspired
“with Dr. Duldulao to have him write scripts for no legitimate
medical purpose.” Doc. 383 at 214. But the jury was free to be-
lieve parts of Gonzalez’s testimony and disregard others.
See
United States v. Takhalov, 827 F.3d 1307, 1321 n.10 (11th Cir.
2016). Thus, the jury reasonably could have concluded that
Duldulao did, in fact, agree to and participate in the conspiracy to
unlawfully distribute controlled substances.
Dudulao is correct that the jury heard other countervailing
evidence: videos of undercover officers’ appointments with
Duldulao showed him asking about their medical history and per-
forming a relatively thorough physical exam. In these videos, he
asked about their current medications and advised them not to
mix the opiates with alcohol. Indeed, Duldulao was acquitted of
the substantive charges that were based on these videos. But
Duldulao’s then-girlfriend Schleisner testified that he told her that
he was “pretty sure” some patients were actually undercover of-
ficers. Doc. 386 at 132. Construing the evidence in favor of the
government, we conclude that a reasonable jury could have
found that these recorded exams were anomalies based on
Dudulao’s suspicions that he was dealing with undercover law
enforcement and that most of the time he adhered to the agree-
ment to write prescriptions for controlled substances for no legit-
imate medical purpose and outside of the usual course of profes-
sional practice.
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20-13973 Opinion of the Court 19
Duldulao also argues that his conspiracy conviction cannot
stand because he was acquitted of the underlying substantive
charges. Not so. Sometimes a jury renders inconsistent verdicts,
but the inconsistency is not a sufficient reason for setting the ver-
dict aside.
See United States v. Powell, 469 U.S. 57, 64–65 (1984).
We have upheld a defendant’s conviction when he was found
guilty of the conspiracy only and not the underlying substantive
offenses.
United States v. Brito, 721 F.2d 743, 749–50 (11th Cir.
1983) (“[I]nconsistency in a jury’s verdict does not require rever-
sal.”) (internal quotation marks omitted). “[A]s long as the guilty
verdict is supported by sufficient evidence, it must stand, even in
the face of an inconsistent verdict on another count.”
United
States v. Mitchell, 146 F.3d 1338, 1345 (11th Cir. 1998). Having
examined the evidence that supports Duldulao’s conspiracy con-
viction and found it to be sufficient, we reject his challenge and
affirm the district court.
2. Santos’s Sufficiency Challenge
We agree with the district court that there was sufficient
evidence to support the jury’s finding that Santos knowingly
joined an agreement to unlawfully dispense controlled substanc-
es. The district court relied on the following evidence: Gonzalez’s
testimony, including an implicit admission on cross examination:
when asked whether he conspired with Santos, Gonzalez said,
“That’s what I’m pleading to,” Doc. 383 at 224; staff and patient
testimony about Santos’s conduct and interactions with patients;
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20 Opinion of the Court 20-13973
staff testimony about HPC’s operations while Santos served as
Medical Director, which still included brief, timed patient visits,
prewritten prescriptions, little to no medical equipment, and no
experienced staffers; and patient testimony about their experienc-
es that confirmed that the clinic’s standard operating scheme un-
der Santos still featured “high patient volume, long-distance pa-
tients, brief medical visits, little to no medical documentation
needed to see the doctor, cash payments, no insurance, cursory
physical examinations, papered and/or inaccurate patient records,
and patients presenting with signs of apparent drug abuse.” Doc.
377 at 8.3 This evidence was sufficient to establish that Santos
knowingly and voluntarily joined an agreement to unlawfully dis-
tribute controlled substances.
3 The district court also relied on Santos’s testimony, in which he admitted
that he agreed to write prescriptions for controlled substances at HPC, de-
spite the many indicators that it was not a legitimate operation. The district
court erred when it relied on Santos’s testimony. When the district court re-
serves ruling on a motion for a judgment of acquittal made after the gov-
ernment’s case-in-chief, the district court’s analysis of the evidence and our
review on appeal is limited to the evidence the government presented.
Unit-
ed States v. Moore, 504 F.3d 1345, 1346 (11th Cir. 2007). Because Santos
moved for a judgment of acquittal at the close of the government’s evidence,
the district court was obligated to follow this snapshot rule and judge the
sufficiency of the evidence based only on the government’s case. It was not
supposed to consider Santos’s testimony at all when it ruled on the Rule 29
motion for acquittal. But this is harmless error; the remaining evidence was
sufficient to deny the motion and convict Santos.
See Barton, 909 F.3d at
1337.
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20-13973 Opinion of the Court 21
Santos argues that the government failed to prove that he
knowingly agreed to write illegal prescriptions. As we noted
above, the agreement element of conspiracy merges with the
knowledge element, and we treat them as a single knowledge re-
quirement. We agree with the district court that there was suffi-
cient evidence to support the jury’s finding that Santos knowingly
joined an agreement to unlawfully dispense controlled substanc-
es. Gonzalez’s testimony shows that Santos knew about the sus-
picious circumstances at HPC. Santos’s tenure at HPC featured
the same red flags that support Duldulao’s conspiracy conviction.
And, unlike Duldulao, Santos was also convicted of substantive
violations based on undercover surveillance, demonstrating that
he knew about and agreed to participate in the conspiracy to un-
lawfully distribute controlled substances.
Gonzalez’s testimony was evidence that Santos knew he
was agreeing to work at a clinic with an unlawful criminal pur-
pose. When Gonzalez interviewed Santos for the Medical Direc-
tor position, he made it clear that he wanted a doctor who would
write controlled substance prescriptions because when “[t]he pa-
tients would come in, they wanted their controlled substances.”
Doc. 383 at 67. Just like he did with Duldulao, Gonzalez showed
Santos a file that contained the types of drugs HPC had pre-
scribed. Santos “was okay with all of it except for he didn’t like
the methadone and the Xanaxes together.”
Id. at 67. Gonzalez no-
tified Santos of the “same format” for timed visits as he had done
with Duldulao, and Santos agreed to write prescriptions under
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22 Opinion of the Court 20-13973
those conditions.
Id. at 68. Santos’s job interview presented cir-
cumstantial evidence that he knew about the criminal scheme.
Other circumstantial evidence about HPC supports an in-
ference that Santos knew about and agreed to the conspiracy.
This evidence included numerous red flags, which we discussed
as to Duldulao and which “all stayed the same” under Santos: the
office had minimal medical equipment or supplies; the staff was
untrained; patients traveled long distances to the clinic; the park-
ing lot was littered with trash, including syringes; and HPC only
accepted cash. Doc. 384 at 117–18. Patients showed signs of drug
addiction, including slurred speech, nodding out, and track marks
on their arms. Regardless, “they got their medications” from San-
tos. Doc. 383 at 115. A jury could reasonably conclude from this
evidence that Santos knew the nature of the conspiracy and
agreed to join it.
The knowledge element also found support in the evidence
of Santos’s conduct. Santos, like Duldulao, signed and postdated
prescriptions when he went on vacations. Patients did not see
Santos while he was on vacation, but they came to HPC and
picked up their postdated prescriptions. Santos also left blank, pre-
signed prescriptions for HPC staff to issue. His conduct supports
an inference that he knew he had agreed to participate in the con-
spiracy to unlawfully distribute controlled substances.
Further, at one point, Santos came into the clinic “real
nervous” and told Gonzalez “that [they] had to start dropping the
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20-13973 Opinion of the Court 23
medications” to lower doses. Doc. 383 at 125. Gonzalez respond-
ed that patients who had been taking high doses could not simply
decrease their doses overnight; they could suffer a heart attack or
a seizure. Santos began lowering prescription doses anyway, tell-
ing Gonzalez there were new guidelines from the federal gov-
ernment to comply with. In fact, the Drug Enforcement Admin-
istration (“DEA”) had recently seized patient records and shut
down a clinic Santos’s wife operated. The jury could have inferred
that Santos was worried that the DEA would raid HPC and dis-
cover that he had been prescribing abnormally high doses of con-
trolled substances.
See Azmat, 805 F.3d at 1028, 1036–37 (uphold-
ing the conviction of a doctor who sometimes decreased patients’
medications for self-serving reasons).
Moreover, Santos was convicted of substantive § 841(a) of-
fenses based on his interactions with purported patients who were
actually government agents. In an undercover video with confi-
dential informant Vasilas, when Santos asked how Vasilas’s sup-
ply of narcotics had held up in the months since his last visit, Vasi-
las said, “I know that I’m not supposed to be saying this but I had
to ask friends and family, you know, to help me out.” Govern-
ment Ex. 207 (segment 003) at 2:30–2:50.4 Santos gave him pre-
scriptions anyway—in fact, Santos gave him three months’ worth
of prescriptions, made him pay three times as though he was ac-
4 This citation refers to Government Exhibit 213, a video recording of the
appointment, which was admitted into evidence at trial.
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24 Opinion of the Court 20-13973
tually coming back in for the two follow-ups, and let his girlfriend
pick up his prescriptions, even though Vasilas had just admitted to
sharing medication. When Chin asked for an increase in her dos-
age, Vasilas told Santos, “I know we’re not supposed to talk about
this, doc, but, you know, . . . she runs out because it’s not enough
for her, so I have to help her out sometimes.”
Id. at 15:30–15:38.
These admissions showed that the patients were diverting their
medication, a serious red flag that suggested they were abusing
drugs.
See Azmat, 805 F.3d at 1032;
Joseph, 709 F.3d at 1090. But
Santos did not even react; instead he gave his patients the in-
creased quantities they wanted. These substantive convictions
show that he participated in the conspiracy and bolster the infer-
ence that he knew about its criminal nature.
Santos contends that “patient testimony and resort to red
flags cannot mend the evidentiary gap [as to an agreement] be-
cause it does not show any agreement between Dr. Santos and
Gonzalez.” Santos Br. at 54. We disagree. Just as with Duldulao,
the jury was entitled to rely on “inferences from the conduct of
the alleged participants or from circumstantial evidence of [the]
scheme” to find an agreement.
Azmat, 805 F.3d at 1035 (internal
quotation marks omitted). Here, Gonzalez’s testimony, the mul-
tiple red flags, and Santos’s conduct together constitute sufficient
evidence that Santos agreed to work at a pill mill and unlawfully
distribute controlled substances. A reasonable jury could find
from this evidence that Santos agreed to be part of a conspiracy to
distribute controlled substances with no legitimate medical pur-
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20-13973 Opinion of the Court 25
pose and outside the scope of professional practice. We reject his
challenge to the sufficiency of the evidence supporting his con-
spiracy conviction.
B. Santos’s Challenge to the Government’s Expert Testimony
Prescriptions for controlled substances are lawful when
they are “issued for a legitimate medical purpose by an individual
practitioner acting in the usual course of his professional prac-
tice.”
Joseph, 709 F.3d at 1094 (quoting 21 C.F.R. § 1306.04(a)). To
convict a doctor for violating 21 U.S.C. § 841(a), the government
must prove that she issued prescriptions with no legitimate medi-
cal purpose or outside of the usual course of professional practice.
Id. The government often uses the testimony of a medical expert
witness to satisfy its burden.
See, e.g.,
Azmat, 805 F.3d at 1036.
But expert medical testimony is not necessary for a conviction.
Joseph, 709 F.3d at 1100. Here, the government called an expert
witness, Dr. Chaitoff, who testified about the definitions of “legit-
imate medical purpose” and “the usual course of professional
practice.”
For the first time, on appeal, Santos argues that Dr.
Chaitoff’s testimony violated the rules of evidence in two ways:
first, by opining on Santos’s subjective mental state, and second,
by reaching a legal conclusion. But the district court’s decision to
admit the testimony was not contrary to binding precedent direct-
ly resolving these legal issues.
United States v. Lejarde–Rada,
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26 Opinion of the Court 20-13973
319 F.3d 1288, 1291 (11th Cir. 2003). Therefore, we discern no
plain error.
A district court may admit expert testimony that “help[s]
the trier of fact to understand the evidence or to determine a fact
in issue.” Fed. R. Evid. 702(a). Generally, “[a]n opinion is not ob-
jectionable just because it embraces an ultimate issue.” Fed. R.
Evid. 704(a). But “[i]n a criminal case, an expert witness 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. Those matters are for the trier of
fact alone.” Fed. R. Evid. 704(b). Rule 704 bars a witness from giv-
ing legal opinions (e.g., “The defendant broke the law”) and from
discussing culpable mental states (e.g., “And he did it knowing-
ly”). An expert witness can give his opinion about an ultimate is-
sue so long as he does not tell the jury what result to reach.
See
Fed. R. Evid. 704 advisory committee’s note. There is a difference
between simply opining on an ultimate issue and impermissibly
directing the jury to a result, however.
See United States v.
Grzybowicz, 747 F.3d 1296, 1310 (11th Cir. 2014).
Santos first argues that Dr. Chaitoff violated Federal Rule
of Evidence 704(b) by testifying about Santos’s subjective mental
state. That argument is not supported by the record, though. Dr.
Chaitoff testified about Santos’s conduct and his professional
opinion of that conduct, but he did not speculate about what was
going on in Santos’s mind.
See United States v. Akwuba,
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20-13973 Opinion of the Court 27
7 F.4th 1299, 1317–18 (11th Cir. 2021) (concluding that medical
experts’ testimony about the defendant’s conduct in issuing pre-
scriptions did not impermissibly give opinions regarding her men-
tal state).
Second, Santos cannot show that there was any plain error
in admitting Dr. Chaitoff’s testimony despite the fact that Dr.
Chaitoff’s testimony reached the ultimate issue of whether Santos
prescribed drugs for no legitimate medical purpose and outside
the usual course of professional practice—the standards of medi-
cal care that govern the case. To summarize Dr. Chaitoff’s testi-
mony, he first gave background testimony about these standards,
explaining that he derived their meanings from the DEA manual,
state and federal regulations, and his own pain management prac-
tice. Giving examples from his experience, he explained the pro-
cess he follows before prescribing controlled substances: finding
out who referred the patient; verifying that the patient has insur-
ance; discussing in detail the patient’s pain complaints and medi-
cal and social history, touching on whether there is a history of
substance abuse; and completing an extensive physical examina-
tion. Before starting someone on controlled substances, he dis-
cusses the medication’s risks and counsels patients about alterna-
tive pain management treatments. He emphasized that there is no
one-size-fits-all approach to treating a patient’s pain.
He also testified about red flags that would warn him that
patients might be abusing their medication: patients with no med-
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28 Opinion of the Court 20-13973
ical records or no referral, those who traveled from long distanc-
es, and those who shared their medication or ran out early. These
are all examples of patients who would prompt further investiga-
tion, according to Dr. Chaitoff. He found red flags when he
watched videos of undercover officer Chin and confidential in-
formant Vasilas visiting Santos’s office. Santos had been prescrib-
ing opiates for Chin for four months. She had missed two months
of appointments, which, Dr. Chaitoff testified, would prompt
most doctors to ask her how she had been managing the pain
without medication and whether she had gone through with-
drawal.
Dr. Chaitoff also noted that it is unusual for a doctor to see
a couple together and perform a brief physical exam on both of
them simultaneously, as Santos did in the video. Reviewing San-
tos’s notes, Dr. Chaitoff testified that there was little documenta-
tion about the results of the physical examinations and why the
injuries warranted treatment with controlled substances. Striking-
ly, Vasilas said that Chin had taken some of his medication, clear
evidence of diversion that Santos did not follow up on. Instead, he
increased her quantity of oxycodone tablets. Dr. Chaitoff gave his
opinion about an ultimate issue when he testified that, at that vis-
it, Santos prescribed Chin and Vasilas controlled substances for no
legitimate medical purpose and outside the scope of professional
practice. Dr. Chaitoff came to the same conclusion about two
other visits. Santos was convicted of substantive charges based on
those three patient visits.
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20-13973 Opinion of the Court 29
It was not plain error to admit Dr. Chaitoff’s ultimate-issue
evidence. Our precedent allows medical experts to testify about
the ultimate issue of the appropriate standard of care. In
Azmat,
the government’s medical expert testified that the patients exhib-
ited an “abundance of red flags” and concluded that the doctor
did not write prescriptions for them for a legitimate medical pur-
pose or in the usual course of professional practice. 805 F.3d at
1036. The defense’s medical expert concluded that the doctor
“act[ed] appropriately under medical standards,” but the jury de-
termined that the government’s expert was more credible and
convicted the defendant.
Id. This Court accepted both experts’
testimony as properly admitted and affirmed the doctor’s convic-
tion.
See id. at 1042–44, 1049. Just as in
Azmat, here it was not
plain error for the district court to admit Dr. Chaitoff’s testimony
for the jury’s consideration.
C. Santos’s Challenge to the Denial of His Motion to Strike
Expert Testimony
Duldulao and Santos both moved to strike Dr. Chaitoff’s
testimony because it relied on evidence the district court had ex-
cluded regarding Duldulao’s other pain clinic, Rehabilitative
Health. The district court granted Duldulao’s motion because Dr.
Chaitoff improperly relied on the excluded evidence to form his
ultimate opinion on whether Duldulao prescribed controlled sub-
stances for no legitimate medical purpose and outside the usual
course of professional practice. By contrast, the court denied San-
tos’s motion because the excluded evidence did not involve him,
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30 Opinion of the Court 20-13973
so Dr. Chaitoff’s opinion about his conduct remained untainted.
Moreover, Santos was not prejudiced because he still had an op-
portunity to effectively cross-examine Dr. Chaitoff and impeach
his credibility.
Santos argues that the district court abused its discretion
when it denied his motion to strike and allowed Dr. Chaitoff to
continue testifying and give his opinion about the propriety of
Santos’s prescriptions. Although the court deemed Dr. Chaitoff a
“less than reliable witness” because of his memory problems and
lack of candor, it was within the court’s discretion to deny San-
tos’s motion to strike. Doc. 388 at 97. Only one topic was off-
limits in Santos’s cross-examination: the evidence about
Duldulao’s other pain clinic that was excluded by the court’s
in
limine order. That limit did not substantially affect Santos’s right
to cross-examine the witness; he could still mitigate any prejudice
through thorough cross-examination.
See United States v. Wil-
liams, 865 F.3d 1328, 1341 (11th Cir. 2017).
D. Santos’s Sentencing Challenge
Lastly, Santos challenges his six-year sentence, contending
that the district court used the wrong standard of proof to calcu-
late the total drug quantity that determined his base offense level.
The government bears the burden of establishing drug quantity
for the purpose of the Sentencing Guidelines by a preponderance
of evidence.
United States v. Rodriguez, 398 F.3d 1291, 1296 (11th
Cir. 2005). The preponderance standard also applies to acquitted
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20-13973 Opinion of the Court 31
conduct; it satisfies due process in both situations.
United States v.
Siegelman, 786 F.3d 1322, 1332 n.12 (11th Cir. 2015). Santos ar-
gues that the clear-and-convincing-evidence standard should ap-
ply here because including his acquitted conduct dramatically in-
creased his sentence. We reject his argument.
The government and Santos initially agreed that Santos’s
sentence should be based on the total drug quantity from his con-
trolled substance prescriptions in all 86 of the patient files that
were admitted at trial, assigning him a base offense level of 32 un-
der the Sentencing Guidelines. Later, Santos objected and asked
the district court to calculate the drug quantity based only on the
prescriptions that the jury had found to be unlawful beyond a rea-
sonable doubt, which would lower his base offense level to 24. He
argued that his partial acquittal meant the court should not gen-
eralize from his three convictions to all 86 patient files. The court
disagreed, finding the drug quantity by a preponderance of the
evidence. It calculated that Santos had a base offense level of 32
and added a two-level enhancement for abusing his position of
trust. On appeal, Santos maintains that the higher standard of
proof should apply.
His argument is foreclosed by precedent. This Court has
consistently held that district courts are required to make factual
findings for sentencing purposes by a preponderance of the evi-
dence.
United States v. Aguilar–Ibarra, 740 F.3d 587, 592 (11th
Cir. 2014). It thus was not error for the district court to determine
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32 Opinion of the Court 20-13973
Santos’s total drug quantity using a preponderance of the evi-
dence standard.
IV. CONCLUSION
For the foregoing reasons, we affirm the district court on
all issues.
AFFIRMED.
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