United States v. Kendrick Eugene Duldulao
Citation87 F.4th 1239
Date Filed2023-11-29
Docket20-13973
Cited21 times
StatusPublished
Full Opinion (html_with_citations)
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[PUBLISH]
In the
United States Court of Appeals
For the Eleventh Circuit
____________________
No. 20-13973
____________________
UNITED STATES OF AMERICA,
Plaintiļ¬-Appellee,
versus
KENDRICK EUGENE DULDULAO,
MEDARDO QUEG SANTOS,
Defendants-Appellants.
____________________
Appeal 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 JORDAN, JILL PRYOR, and TJOFLAT, Circuit Judges.
JILL PRYOR, Circuit Judge:
This multidefendant criminal appeal is before us on remand
from the Supreme Court of the United States. After we affirmed
the convictions of Kendrick Eugene Duldulao and Medardo Queg
Santos for the roles they played in a Florida āpill mill,ā the Supreme
Court vacated our judgment and remanded for further considera-
tion in light of Ruan v. United States, 142 S. Ct. 2370 (2022) (āRuan
IIā). See United States v. Duldulao, No. 20-13973, 2021 WL 6071511
(11th Cir. Dec. 21, 2021) (unpublished), vacated sub nom. Santos v.
United States, 143 S. Ct. 350 (2022). With the benefit of the Supreme
Courtās guidance, supplemental briefing, and oral argument, we
now affirm in part, vacate in part, and remand in part for a new
trial.
I. BACKGROUND
This appeal concerns the criminal convictions of two doc-
tors, Duldulao and Santos, who participated in a āpill millāāa 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. See United States
v. Azmat, 805 F.3d 1018, 1025 n.1 (11th Cir. 2015). Duldulao and
Santos served sequentially as Medical Directors of a pain manage-
ment clinic in Tampa, Florida called Health and Pain Clinic
(āHPCā). HPC liberally dispensed controlled substances to its pa-
tients, who paid with cash or credit, exhibited obvious signs of drug
addiction, and received little attention from doctors. A jury
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20-13973 Opinion of the Court 3
convicted both Duldulao and Santos of conspiracy to distribute and
dispense controlled substances not for a legitimate medical purpose
and not in the usual course of professional practice, violating 21
U.S.C. Ā§ 846. The jury also convicted Santos of multiple substantive
counts of distributing controlled substances not for a legitimate
medical purpose and outside the usual course of professional prac-
tice, violating 21 U.S.C. Ā§ 841.
Duldalao and Santos became involved with HPC in 2011 and
2014, respectively, when Ernest Gonzalez, the de facto owner of
HPC, hired them to work at his pill mill. Gonzalez knew that the
patients āwere coming in [] to get controlled substances,ā so, at
Duldulaoās and Santosās respective job interviews, Gonzalez made
it clear that HPCās patients expected to receive controlled sub-
stances during their visits. Doc. 382 at 38. 1 Gonzalez confirmed
that Duldalao knew the clinic āneed[ed] a doctor who was going to
do controlled substancesā and discussed specific controlled sub-
stances that Duldulao would use to treat the clinicās patients. Doc.
382 at 36. Gonzalez also told Duldulao and Santos about key as-
pects of the business model: very short, timed patient appoint-
ments; high patient volume (30ā40 patients per day); and up-front
payment onlyāHPC did not accept insurance.
Other characteristics suggested that the clinic was not a le-
gitimate medical operation. The clinic had barely any medical
equipmentāonly an exam table for the patients to sit onāor
1 āDoc.ā refers to the district courtās docket entries.
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4 Opinion of the Court 20-13973
supplies. HPC staff who ran the front desk and did patient intake
had no medical or administrative training. Yet they wrote prescrip-
tions for controlled substances for the doctor to sign after each pa-
tientās brief visit.
HPCās patients exhibited obvious signs of substance abuse.
Witnesses described them as having bloodshot eyes, slurring their
words, looking sleepy, and stumbling when they walked. Some pa-
tients had visible track marks, indicating intravenous drug abuse.
Others looked like they were going through opiate withdrawalā
sweating, shaking, vomiting, and experiencing hot and cold flashes.
People were ānodding outā in the waiting room and āshooting upā
in the parking lot. Doc. 384 at 100; Doc. 387 at 42. Patients hung
out in the parking lot and left behind trash like baggies, blunt wrap-
pers, and syringes.
The clinic administered drug tests, but patients sometimes
bribed HPC staff to skip the drug test. The staff falsified test records
after letting patients skip the test. When patients who actually took
drug tests tested positive for illegal drugs, HPC staff would some-
times mark a negative result in their file and allow the patients to
receive prescriptions anyway.
It was easy to get controlled substances at HPC: according
to witnesses, HPC patients always left with new prescriptions for
controlled substances. To obtain prescription medication, HPC pa-
tients needed little documentation of a condition that required pain
managementājust an MRI within the last two years documenting
a physical abnormality of some kind. That and a Florida driverās
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20-13973 Opinion of the Court 5
license got the patients prescriptions for controlled substances like
oxycodone and methadone.
Duldalao and Santos participated in these practices. During
patient appointments, Duldulao conducted cursory medical exam-
inations. 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
medical exam at all. He wrote prescriptions for controlled sub-
stances for patients even when they bore visible track marks or had
traveled from long distancesāboth red flags for controlled sub-
stance abuse, according to the governmentās medical expert wit-
ness, Dr. Kevin Chaitoff. Duldulao prescribed controlled sub-
stances in dangerous combinations, allowing his patients to mix
Xanax, methadone, and a muscle relaxer called Soma. He even ad-
mitted to his girlfriend that he worked at a āpain mill.ā Doc. 386 at
143.
When Santos replaced Duldulao as HPCās Medical Director,
little changed at HPC. Like Duldulao, 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
patientās 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 pre-
scribed drugs in the same dangerous combinations that Duldulao
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6 Opinion of the Court 20-13973
had. Santos, too, went on vacations and 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 āboyfriend,ā a confidential informant named Robert
Vasilas. Over the course of a little over a year, Chin and Vasilas
made a series of five visits to Santos that would later serve as the
basis for three of Santosās convictions.
Chin (without Vasilas) made the first of these visits to HPC
and Santos in July 2014. Chin presented as a new patient with no
medical documentation and vague complaints of lower back pain
lacking any obvious cause that over the counter medication would
not alleviate. During a brief visit, Santos joked about DEAās āpro-
hibitionā on controlled substances resulting in the closure of many
pain clinics. Doc. 372-208 at 4:30ā5:10. 2 And Chin used slang (ā30sā
and ā15sā of āOxyā) to describe quantities and types of controlled
substances, suggesting a potential substance-abuse problem. Id. at
5:10ā5:20. Nevertheless, after a cursory examination in which San-
tos discussed no alternative forms of treatment, Santos wrote Chin
a prescription for hydrocodone, which Santos changed to a pre-
scription for oxycodone a few days later. Chin told Santos that she
would fill the prescriptions in Alabama.
2 At trial, the government introduced videos of interactions between Santos
and the agents. Our citations to Doc. 372 (the governmentās trial exhibit list)
refer to these videos by their exhibit numbers.
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20-13973 Opinion of the Court 7
Santos saw Chin again a few months later. During her visit
to HPC, Chin asked Santos for more controlled substances and told
him that she had run out of oxycodone becauseāalthough she ex-
perienced no increase in paināshe had been ādoubling,ā taking
more than the prescribed amount. Doc. 372-212 at 11:00ā12:15.
Santos agreed to provide 10 extra pills. Chin also asked if Santos
could provide her medication through a smaller number of pills at
a higher dosage (30 mg) When Santos expressed surprise that Chin
could get high-dose oxycodone, Chin explained that she and her
boyfriend both received controlled substances from pain clinics by
driving two hours round trip to Alabama, where pharmacies re-
quired less stringent documentation to dispense large amounts of
controlled substances. Chin said she was already receiving 30 mg
pills there, implying she had multiple sources of controlled sub-
stances. Id. at 0:42ā0:44 (āIn Alabama Iām gettinā em.ā). And Chin
revealed that she lived in Panama City, meaning she travelled al-
most 400 miles to HPCās Tampa location. Nevertheless, Santos
wrote Chin a prescription that increased the total amount of con-
trolled substances she received and gave her access to higher-dose
pills.
At Chinās next visit, Vasilas came with her. Vasilas, a return-
ing patient, told Santos that Chin was ārobbingā him of his pills
when she ran out of hers. Doc. 386 at 173. Instead of investigating
this red flag, Santos gave both of them prescriptions for greater
quantities of oxycodone. He also wrote Vasilas a new prescription
for Xanax without asking Vasilas about his history with anxiety or
what tools he used to manage it. He started Vasilas on Xanax, even
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8 Opinion of the Court 20-13973
though most doctors would not have prescribed that drug to some-
one who was also taking an opioid. At no point did Santos discuss
alternative treatments or milder medications with either patient.
Chin later made another visit to Santos without Vasilas. In
an earlier visit, Santos had agreed to give Chin prescriptions to take
to Vasilas, who said he would be out of town for work. Santos told
Chin she would have to pay (cash, of course) for a visit for Vasilas,
even though Vasilas would not be present. Santos gave her pre-
scriptions for the absent Vasilas, even filling out Vasilasās file as
though Santos had examined him.
In a final visit, Chin and Vasilas returned to see Santos to-
gether. Vasilas told Santos that he had run out of his pills and had
been getting medications from friends and family. Santos re-
sponded by giving Vasilas extra prescriptions with a ādo not fill un-
tilā date; Santos charged him for the prescriptions written in ad-
vance.
After collecting evidence (including videos) through these
undercover visits, the government indicted Santos, Duldulao, and
Gonzalez. Gonzalez pled guilty and testiļ¬ed against Santos and
Duldulao. Based on their conduct at HPC, a second superseding
indictment charged Duldulao and Santos each with one count of
conspiracy to distribute and dispense oxycodone, hydromorphone,
morphine, methadone, and hydrocodone (Schedule II controlled
substances) and alprazolam (Xanax, a Schedule IV controlled sub-
stance), not for a legitimate medical purpose and not in the usual
course of professional practice, violating 21 U.S.C. Ā§ 846. It also
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20-13973 Opinion of the Court 9
charged both men with multiple substantive counts of distributing
controlled substances not for a legitimate medical purpose and not
in the usual course of professional practice, violating 21 U.S.C.
Ā§ 841. Santos faced ļ¬ve counts under Ā§ 841: one for each of the ļ¬ve
visits made by Chin and Vasilas we have described.
At trial, the government established the facts surrounding
Duldulaoās and Santosās conduct through the testimony of Gonza-
lez, government agents, HPC patients, and HPC employees. The
government also called Dr. Chaitoļ¬ as an expert in pain manage-
ment treatment. Dr. Chaitoļ¬ testiļ¬ed about how he practices pain
management, underscoring how it diļ¬ers from the conduct of the
doctors and staļ¬ of HPC. In his practice, Dr. Chaitoļ¬ conducts a
comprehensive physical exam on patients; speaks with them about
their medical history, their current pain, and the narcotics agree-
ment patients are required by law to sign; and typically allots 30 to
35 minutes for an initial visit and 20 minutes for a follow-upāmuch
longer than the appointments patients received with Duldulao or
Santos. He testiļ¬ed 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 also opined that āmost ofā the prescriptions that
Santos wrote for controlled substances āwere provided for no le-
gitimate medical purpose, [and] they were not issued in the course
of oneās professional practice.ā Doc. 388 at 20. Santos moved to
strike his testimony, but the district court denied the motion,
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10 Opinion of the Court 20-13973
noting that Santos could cross-examine Dr. Chaitoff to challenge
his credibility.
After the government rested its case, both Duldulao and
Santos moved for a judgment of acquittal. At the trialās conclusion,
the district court granted Duldulaoās motion as to most of the sub-
stantive counts of dispensing and distributing controlled substances
but otherwise denied the motions.
The jury convicted both Duldulao and Santos of the conspir-
acy count. It also convicted Santos of three substantive violations
of 21 U.S.C. Ā§ 841 and acquitted him of two others.
Duldulao and Santos appealed on four grounds. Both men
challenged the sufficiency of the evidence as to their conspiracy
convictions under 21 U.S.C. Ā§ 846. Santos challenged the admission
of Dr. Chaitoffās expert testimony about his treatment of patients.
Santos also challenged the district courtās denial of his motion to
strike Dr. Chaitoffās testimony. Finally, Santos challenged the cal-
culation of his sentence. We considered each ground and, with the
benefit of oral argument, affirmed. Duldulao, 2021 WL 6071511.
After we affirmed, the Supreme Court addressed liability un-
der 21 U.S.C. Ā§ 841in Ruan v. United States,142 S. Ct. 2370
(2022)
(āRuan IIā). Ruan II overruled our precedent addressing the scienter
requirement under that statute. Id. at 2382.
Title 21 Ā§ 841 makes it a federal crime āexcept as authorized,
for any person knowingly or intentionally to manufacture, distrib-
ute, or dispense a controlled substance.ā Id. at 2374ā75 (internal
quotation marks omitted) (alterations adopted). Federal
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20-13973 Opinion of the Court 11
regulations in turn authorize doctors to prescribe controlled sub-
stances āfor a legitimate medical purpose . . . in the usual course of
. . . professional practice.ā 21 C.F.R. Ā§ 1306.04(a). Thus, a doctor vi-
olates 21 U.S.C. Ā§ 841 when he distributes or dispenses a controlled
substance either not for a legitimate medical purpose or outside the
usual course of professional practice. See United States v. Abovyan,
988 F.3d 1288, 1305 (11th Cir. 2021) (holding that a violation of ei-
ther prong is sufficient to violate Ā§ 841); see also United States v. Hea-
ton, 59 F.4th 1226, 1241 n.17 (11th Cir. 2023) (concluding that this
holding of Abovyan survived Ruan II).
Before Ruan II, our precedent required the government to
show that a defendant subjectively knew he was acting not for a
legitimate medical purpose under Ā§ 841. United States v. Tobin, 676
F.3d 1264, 1282 (11th Cir. 2012). But it did not require the same
showing with respect to whether a doctor violated Ā§ 841 by pre-
scribing a controlled substance outside the usual course of profes-
sional practice. Id.; see also United States v. Williams, 445 F.3d 1302,
1309ā10 (11th Cir. 2006); United States v. Merrill, 513 F.3d 1293,
1305ā06 (11th Cir. 2008). Instead, our cases explained that, when it
came to whether a physician acted outside the usual course of pro-
fessional practice, āthe appropriate focus is not on the subjective
intent of the doctorā but rather on āwhether, from an objective
standpoint, the controlled substances were dispensed in the usual
course of professional practice.ā Tobin, 676 F.3d at 1282 (internal
quotation marks omitted) (alteration adopted).
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12 Opinion of the Court 20-13973
Ruan II rejected that distinction. Overruling our decision in
United States v. Ruan, 966 F.3d 1101 (11th Cir. 2020) (āRuan Iā), the
Supreme Court held that the scienter provision of 21 U.S.C.
Ā§ 841(a) (āknowingly or intentionallyā) applies to both prongs of
the authorization exception. Ruan II, 142 S. Ct. at 2382. To establish
criminal liability under Ā§ 841, it therefore is not enough for the gov-
ernment to prove that a defendant acted outside the usual course
of professional practice by violating an objective standard of care.
Rather, Ruan II requires the government to prove that āthe defend-
ant knowingly or intentionally acted in an unauthorized man-
nerāāthat the defendant knew he was acting outside the usual
course of professional practice or intended to. Id. The Supreme
Court criticized an objective standard, like the one we had applied,
as reducing the requirements for criminal culpability under
Ā§ 841āto negligence.ā Id. at 2381.
After we affirmed Santosās conviction (and while Ruan II was
pending before the Supreme Court), Santos petitioned for a writ of
certiorari. Pet. for Writ of Cert., Santos v. United States, 143 S. Ct.
350 (2022) (No. 21-1418). Following its decision in Ruan II, the Su-
preme Court granted the petition, vacated our judgment, and re-
manded for further consideration in light of Ruan II. Santos, 143 S.
Ct. at 350. This appeal is now before us again. 3
3 Although only Santos petitioned for certiorari, we permitted both parties to
participate in this remand. After all, we entered a single judgment as to both
Santos and Duldulao. And the Supreme Court vacated ā[t]he judgment.ā Judg-
ment, Santos v. United States, 143 S. Ct. 350 (No. 21-1418).
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20-13973 Opinion of the Court 13
II. STANDARD OF REVIEW
āWe review the sufficiency of the evidence de novo when, as
here, the defendant[s] have preserved [their] claim[s] by moving
for . . . judgment[s] of acquittal.ā Azmat, 805 F.3d at 1035.
In a criminal appeal, we review issues not raised at trial for
plain error, which āoccurs if (1) there was error, (2) that was plain,
(3) that affected the defendantās substantial rights, and (4) that seri-
ously affected the fairness, integrity, or public reputation of judicial
proceedings.ā United States v. Wright, 607 F.3d 708, 715 (11th Cir.
2010) (internal quotation marks omitted); see also Fed. R. Crim. P.
52(b). An error is plain if it is āclearā or āobvious.ā United States v.
Olano, 507 U.S. 725, 734 (1993). When āthe explicit language of a
statute or rule does not specifically resolve an issue, there can be
no plain error where there is no precedent from the Supreme Court
or this Court directly resolving it.ā United States v. Chau, 426 F.3d
1318, 1322 (11th Cir. 2005) (internal quotation marks omitted).
We review the district courtās denial of a motion to strike
testimony for an abuse of discretion. United States v. Woody, 567
F.2d 1353, 1357 (5th Cir. 1978). 4 We will reverse only if we find an
error that affected the defendantās substantial rights. See United
States v. Barton, 909 F.3d 1323, 1337 (11th Cir. 2018).
4 Decisions of the Fifth Circuit issued before October 1, 1981 are binding prec-
edent in this circuit. Bonner v. City of Prichard, 661 F.2d 1206, 1207 (11th Cir.
1981) (en banc).
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14 Opinion of the Court 20-13973
We review a district courtās application of the Sentencing
Guidelines de novo. United States v. Johnson, 980 F.3d 1364, 1374
(11th Cir. 2020).
III. DISCUSSION
On remand, Duldulao and Santos renew the challenges we
addressed in our now-vacated opinion affirming their convictions
and Santosās sentence. For the first time, on remand, they add that
the jury was improperly instructed. According to Duldulao and
Santos, the instructions the jury received regarding the Ā§ 846 con-
spiracy counts and the Ā§ 841 substantive counts failed to convey the
mens rea Ruan II requires. We conclude that only the challenge to
the Ā§ 841 jury instructions has merit. We therefore affirm
Duldulaoās conviction under Ā§ 846, affirm Santosās conviction un-
der Ā§ 846, vacate Santosās convictions under Ā§ 841, and vacate San-
tosās sentence.
A. Ā§ 846 Jury Instructions
The jury convicted both Duldulao and Santos of conspiracy
to distribute and dispense controlled substances without authori-
zation, violating 21 U.S.C. Ā§ 846. On remand, they challenge the
propriety of the district courtās jury instruction on conspiracy un-
der Ruan II. The United States responds that we cannot reach the
jury instruction because the defendants invited any error. See
United States v. Maradiaga, 987 F.3d 1315, 1322ā23 (11th Cir. 2021).
Invited or not, our decision on remand in United States v.
Ruan, 56 F.4th 1291(11th Cir. 2023) (āRuan IIIā), cert. denied,2023 WL 7287134
(U.S. Nov. 6, 2023) (No. 22-1175), precludes us from
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20-13973 Opinion of the Court 15
finding error in the district courtās conspiracy instruction. In Ruan
III, we reviewed de novo (and upheld) a district courtās conspiracy
instruction under 21 U.S.C. Ā§ 846. Id. at 1296, 1299. Although we
found the jury instruction as to the substantive Ā§ 841 charge incon-
sistent with Ruan II, we nevertheless concluded that the conspiracy
instruction āconveyed the adequate mens rea.ā Id. at 1299. We
reached that conclusion because, despite any defect in the instruc-
tion as to the substantive counts, āthe conspiracy instructions al-
ready required [the jury] to find that the defendant acted with sub-
jective knowledge.ā Id. Those instructions required the jury to find
that the defendants āagreed to try and accomplish a shared unlaw-
ful plan to distribute or dispenseā controlled substances and that
they āknew the unlawful purpose of the plan and willfully joined
it.ā Id. The jury was further instructed that āa person acts with will-
fulness only when they act voluntarily and purposefully to do
something the law forbids.ā Id. (internal quotation marks omitted)
(alterations adopted). Based on these instructions, we concluded
the jury could not have convicted the Ruan defendants if it thought
they subjectively believed their actions fell within the professional
practice of medicine. Id.
What was true of that conspiracy instruction is true of this
one. The district court instructed the jury that the government was
required to prove that:
two or more persons in some way agreed to try to
accomplish a shared and unlawful plan as charged in
the second superseding indictment; and that the de-
fendant knew the unlawful purpose of the plan and
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16 Opinion of the Court 20-13973
willfully joined in it; and that the object of the unlaw-
ful plan was to distribute and dispense, and cause the
distribution and dispensing of [controlled substances]
for no legitimate medical purpose and outside the
usual course of professional practice.
Doc. 392 at 179. The court further instructed that āwillfully means
that the act was committed voluntarily and purposely, with the in-
tent to do something the law forbids.ā Id.at 183. Thus, the district
court instructed the jury that it could convict Duldulao and Santos
only if it found that they subjectively knew the object of the con-
spiracy was to distribute controlled substances without authoriza-
tion.
In their supplemental reply briefsāļ¬led after Ruan IIIā
Santos and Duldulao do not argue that the conspiracy jury instruc-
tions here are distinguishable from those given in Ruan III. To the
contrary, Santos (whose brief Duldulao joined) states that ā[t]he in-
structions in Ruan and this case arenāt diļ¬erent in any material re-
spect.ā Santos Supp. Reply Br. at 6. Instead, they contend that Ruan
III either ļ¬unks our prior panel precedent rule or it should be re-
considered. As a panel of this Court, we have no authority to revisit
the holding of Ruan III. See Scott v. United States, 890 F.3d 1239,
1256ā57 (11th Cir. 2018). And under our prior panel precedent rule,
Ruan III controls.
Our prior panel precedent rule compels us to obey the hold-
ing of āļ¬rst [panel] in this Circuit to address [an] issue.ā Smith v.
GTE Corp., 236 F.3d 1292, 1302 (11th Cir. 2001). That is so even if a
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20-13973 Opinion of the Court 17
subsequent panel has reached a result contrary to the prior panel.
Id. The rule governs āunless and untilā the ļ¬rst panelās opinion āis
overruled or undermined to the point of abrogation by the Su-
preme Court or by this court sitting en banc.ā United States v. Archer,
531 F.3d 1347, 1352 (11th Cir. 2008). Duldulao and Santos point out
that the Tenth Circuitāin a case consolidated with Ruan II before
the Supreme Courtārecently held that a faulty Ā§ 841 instruction
āinfectedā each of the defendantās convictions, including the con-
spiracy conviction under Ā§ 846. United States v. Kahn, 58 F.4th 1308,
1311, 1321ā22 (10th Cir. 2023). But the Tenth Circuitās decision in
Kahn does not deny our prior precedent rule its force: āonly the
Supreme Court or this court sitting en banc can judicially overrule
a prior panel decision.ā United States v. Brown, 342 F.3d 1245, 1246
(11th Cir. 2003) (internal quotation marks omitted). In deciding this
appeal, we must adhere to Ruan III.
Duldulao and Santos also try to direct us to United States v.
High, 117 F.3d 464 (11th Cir. 1997), as the relevant prior panel prec-
edent. Like this case, High was a criminal appeal involving a drug
conspiracy. Id. at 465. But in High, the government alleged that the
defendants conspired to launder drug proceeds (violating 18 U.S.C.
Ā§ 1956), structure transactions to avoid regulatory scrutiny (violat-
ing 31 U.S.C. Ā§ 5324), and defraud the United States (violating18 U.S.C. Ā§ 981
). Id. at 469. Instead of charging the defendants with
three separate conspiracy counts or seeking a special verdict iden-
tifying the basis for each conviction, the government sought and
obtained a general conspiracy verdict against the defendants. Id. at
470. Because the district court wrongly instructed the jury on the
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18 Opinion of the Court 20-13973
mens rea requirement for the underlying structuring oļ¬ense and
we could not determine which underlying oļ¬ense was the basis for
conviction, we concluded that we needed to reverse. Id.
Highās holding rested on our conclusion that the conspiracy
instruction did not cure the erroneous instruction as to the conspir-
acyās object. Id. The conspiracy instruction, together with the
structuring instruction, failed to convey the necessary mens rea for
convicting the defendants of conspiracy to engage in structuring in
violation of 31 U.S.C. Ā§ 5324. See Ratzlaf v. United States,510 U.S. 135
, 136ā37 (1994). In contrast, in Ruan III, we decided that the con-
spiracy instruction adequately conveyed the required mens rea and
was not erroneous, so Ruan III did not contradict Highās holding
about how to proceed when instructional error does exist. Ruan III,
56 F.4th at 1299 (concluding that āthe instructions for the drug con-
spiracy charges were not erroneousā). Nor would it be fair to say
that Highās contextual analysis of one speciļ¬c jury instruction re-
quired the Ruan III panel to conclude that a very diļ¬erent set of
instructions also was error. See United States v. Cochran, 683 F.3d
1314, 1319 (11th Cir. 2012) (explaining that we āanalyze the ob-
jected-to portion of [jury] instructions in light of the entire chargeā
(internal quotation marks omitted)). Ruan III does not conļ¬ict with
High. 5
5 Because we conclude Ruan III is the controlling prior panel precedent, we
need not consider whetherāas the government arguesāintervening Su-
preme Court precedent has abrogated Highās remedial holding.
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20-13973 Opinion of the Court 19
Ruan III controls and requires us to conclude that the instruc-
tions the jury received describing the elements of a conspiracy un-
der Ā§ 846 were proper.
B. Ā§ 841 Jury Instructions
Besides one count of Ā§ 846 conspiracy, the jury convicted
Santos of three counts of dispensing and distributing, and causing
the distribution and dispensing of, controlled substances not for a
legitimate medical purpose and not in the usual course of profes-
sional practice, in violation of 21 U.S.C. Ā§ 841. On remand, Santos
challenges the district courtās instructions to the jury on these
counts as inconsistent with Ruan II. The government argues that
any instructional error was āinvitedā and thus cannot support re-
versal. Because we agree with Santos that the jury instructions re-
garding Ā§ 841 amounted to plain error, we address the govern-
mentās invited-error argument.
Under the doctrine of invited error, on appeal, āa party may
not challenge as error a ruling or other trial proceeding invited by
that party.ā Ford ex rel. Estate of Ford v. Garcia, 289 F.3d 1283, 1293ā
94 (11th Cir. 2002) (internal quotation marks omitted). Proposing
the language of a jury instruction is āa textbook case of invited er-
rorā under our precedent. Maradiaga, 987 F.3d at 1322. As the gov-
ernment points out, the defense proposed at least some of the jury
instruction to which it now objects. And, in an unpublished opin-
ion, we have applied the invited error doctrine to a similar set of
circumstances in a post-Ruan II case. United States v. Mencia, No. 18-
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20 Opinion of the Court 20-13973
13967, 2022 WL 17336503, at *13 (11th Cir. Nov. 30, 2022) (un-
published).
The doctrine of invited error applies when an error is āat-
tributable to the action of the defense.ā United States v. Jones, 743
F.3d 826, 828 n.1 (11th Cir. 2014) (internal quotation marks omit-
ted). It prevents litigants from sandbagging district courts by āin-
troducing error at trial with the intention of creating grounds for
reversal on appeal.ā United States v. Stone, 139 F.3d 822, 839 (11th
Cir. 1998). And it enforces the notion, rooted in fairness, that
āsomeone who invites a court down the primrose path to error
should not be heard to complain that the court accepted its invita-
tion.ā Doe v. Princess Cruise Lines, Ltd., 657 F.3d 1204, 1213 (11th Cir.
2011).
Considering the doctrineās purposes, our sister circuits rec-
ognize an exception where the āerrorā invited by a party ārelied on
settled law that changed while the case was on appeal.ā United
States v. Titties, 852 F.3d 1257, 1264 n.5 (10th Cir. 2017); see also
United States v. Andrews, 681 F.3d 509, 517 n.4 (3d Cir. 2012). We join
them in recognizing this exception and conclude that it applies in
the harsh circumstances of this case.
According to the government, Santos should have proposed
jury instructions that were inconsistent with then-binding and
longstanding circuit precedent holding that whether a physician
acts in the usual course of professional practice is judged objec-
tively. Before Ruan II, we reiterated that holding many times in pub-
lished opinions dating back at least to 2006. Tobin, 676 F.3d at 1282ā
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20-13973 Opinion of the Court 21
83; Merrill, 513 F.3d at 1305ā06; Williams, 445 F.3d at 1309ā10. We
maintained unļ¬aggingly that āthe law requires only that the jury
ļ¬nd the doctor prescribed a drug . . . not āin the usual course of
professional practiceāāānot that the doctor subjectively knew she
was acting outside the practice of medicine. Abovyan, 988 F.3d at
1308. We rejected jury instructions that attempted to say other-
wise. United States v. Joseph, 709 F.3d 1082, 1097 (11th Cir. 2013); see
also United States v. Ruan, 966 F.3d 1101, 1167 (11th Cir. 2020) (āThis
Court has repeatedly rejected [jury] instructions . . . [that] failed to
include the objective standard by which to judge the physicianās
conduct.ā). And we turned away attempts to have us revisit the
question sitting en banc. See Order Den. Pet. for Panel Rehāg or
Rehāg En Banc, United States v. Ruan, No. 17-12653 (11th Cir. Nov.
4, 2020). What is more, there was no indication during this trial that
the Supreme Court might unwind that precedential juggernaut.
The jury here reached its verdicts more than two years before the
Supreme Court granted certiorari in Ruan II. Requiring litigants to
propose jury instructions inconsistent with established circuit prec-
edent on the oļ¬-chance of Supreme Court intervention would not
promote the invited-error doctrineās purpose. By acknowledging at
trial that under our law ā[w]hether the Defendant acted outside the
usual course of professional practice is to be judged objectively,ā
Doc. 320 at 37, Santos demonstrated neither āa lack of diligence,ā
nor a desire to mislead the district court, ābut merely a want of
clairvoyance.ā Joseph v. United States, 135 S. Ct. 705, 706 (2014) (Ka-
gan, J., respecting the denial of certiorari).
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22 Opinion of the Court 20-13973
The governmentās position diverges as well from broader
principles governing our review. In this criminal appeal, applying
the doctrine would undermine the principle that ā[d]ecisions of the
Supreme Court construing substantive federal criminal statutes
must be given retroactive eļ¬ect.ā United States v. Peter, 310 F.3d 709,
711(11th Cir. 2002); see also Griļ¬th v. Kentucky,479 U.S. 314, 328
(1987) (ā[A] new rule for the conduct of criminal prosecutions is to
be applied retroactively to all cases, state or federal, pending on di-
rect review or not yet ļ¬nal . . . .ā). And it would be inconsistent
with our approach in other contexts. For instance (subject to plain
error review), we allow an appellant to raise new arguments based
on intervening precedent. United States v. Durham, 795 F.3d 1329,
1330ā31 (11th Cir. 2015) (en banc). Similarly, in the 28 U.S.C. Ā§ 2255
context we excuse procedural defaultāwhich, like invited error,
operates as a complete bar to reviewāwhen there has been an in-
tervening change in the law, despite the strong ļ¬nality interests at
play in the habeas context. Seabrooks v. United States, 32 F.4th 1375,
1384 (11th Cir. 2022). In these ways, we often recognize that the
failure to anticipate an abrupt change in precedent is blameless and
should not preclude appellate review.
The government points to our decision in Maiz v. Virani, 253
F.3d 641 (11th Cir. 2001), to argue that we may not craft an excep-
tion to the application of invited error. Maiz was a civil case involv-
ing RICO claims against a group of companies who engaged in an
allegedly fraudulent real estate investment scheme. Id. at 650. In
1990, we had adopted one approach to the statute of limitations for
a civil RICO claim; other circuits had adopted another. Compare
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20-13973 Opinion of the Court 23
Bivens Garden Oļ¬. Bldg., Inc. v. Barnett Bank of Fla., Inc., 906 F.2d
1546, 1554 (11th Cir. 1990) (adopting one accrual rule), with Rotella
v. Wood, 147 F.3d 438, 440 (5th Cir. 1998) (adopting another accrual
rule). Ten years later, the Supreme court settled the debate, over-
turning our civil RICO accrual rule. Rotella v. Wood, 528 U.S. 549,
553ā54 (2000).
Against that backdrop, the defendants in Maiz raised the
four-year limitations period for civil RICO claims as an aļ¬rmative
defense. 253 F.3d at 676; see also Agency Holding Corp. v. Malley-Duļ¬
& Assocs., Inc., 483 U.S. 143, 156 (1987) (establishing limitations pe-
riod). To deļ¬ne that aļ¬rmative defense, the defendants crafted and
proposed a jury instruction consistent with our accrual rule in
Bivens Garden, which the district court adopted. Maiz, 253 F.3d at
676. The jury then rejected the defense and found the defendants
liable. Id. While their appeal was pending, the Supreme Court de-
cided Rotella and clariļ¬ed the accrual rule for a civil RICO claim. Id.
at 676ā77.
The defendants argued that invited error does not apply
when a jury āinstruction is rendered incorrect by an intervening
change in the governing lawā and that āRotella [was] such a change
in the law.ā Id. at 677. We did not reject such a rule outright; rather,
we determined that Maiz was not āan appropriate [case] to carve
out an exception to the invited error rule.ā Id. We noted that the
defendants in Maiz had not shown āthat the district courtās instruc-
tion was probably responsible for an incorrect verdict.ā Id. (internal
quotation marks omitted). And the defendants had not shown that
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24 Opinion of the Court 20-13973
theirs was the āexceptionalā civil case justifying reversal on plain
error review. Id. We also observed that the defendants in Maiz āhad
reasonable grounds for declining to proposeāand, if necessary,
stating an objection toāthe [accrual] instruction that instead they
asked the court to give.ā Id.
Unlike Maiz, we view this as the appropriate case to recog-
nize an exception to the ordinary rule. The change in law asserted
in Maiz concerned a limitations defense to a civil action; in contrast,
this case involves the substantive elements of a criminal oļ¬ense.
And, as we conclude below, on this caseās facts we harbor grave
doubts that the jury would have reached the same outcome had it
been properly instructed. Moreover, distinct from Maiz, where the
defendant was solely responsible for the challenged instruction, the
government bears some of the blame for this error, too. Our review
of the record indicates that although the government is correct that
the defense proposed language to which it now objects, the govern-
ment proposed the same language. This was unsurprising be-
causeāas the government noted in its proposed jury instruc-
tionsāit was the very same language we had approved in at least
four prior cases. The defense did not craft this error itself.
To be clear, we are not authorizing a free-roving change-in-
law exception to the rule of invited error. We hold only that on the
facts of this caseāa criminal appeal involving an instructional error
in deļ¬ning a substantive oļ¬ense ļ¬owing directly from our long-
standing and clear precedent and attributable to both partiesāwe
will not invoke the doctrine.
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20-13973 Opinion of the Court 25
Because we reject the governmentās invitation to apply the
doctrine of invited error, we instead review the district courtās jury
instructions for plain error.6 See Greer v. United States, 141 S. Ct.
2090, 2096 (2021). A defendant bears the āburden of establishing
entitlement to relief for plain error.ā Id. at 2097 (internal quotation
marks omitted). To do so, a defendant must show four things:
āFirst, there must be an error. Second, the error must be plain.
Third, the error must aļ¬ect substantial rights, which generally
means that there must be a reasonable probability that, but for the
error, the outcome of the proceeding would have been diļ¬erent.ā
Id. at 2096 (internal quotation marks and emphasis omitted).
Fourthāif a defendant makes these ļ¬rst three showingsāwe con-
sider whether the error āseriously aļ¬ects the fairness, integrity or
public reputation of judicial proceedings.ā United States v. Olano,
507 U.S. 725, 736 (1993) (internal quotation marks omitted) (altera-
tion adopted). Meeting this test is ādiļ¬cult.ā Greer, 141 S. Ct. at
2097 (internal quotation marks omitted). Nevertheless, after con-
sidering each required showing in turn, we conclude that we must
vacate Santosās Ā§ 841 convictions.
Taking the ļ¬rst two showings together, the district courtās
instruction was error, and the error is plain. Consistent with our
since-overruled precedent, the district court instructed the jury that
6 Santos and the government agree that if the invited error doctrine does not
apply, then plain error does.
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26 Opinion of the Court 20-13973
to obtain a conviction under 21 U.S.C. Ā§ 841, the government
needed to prove:
First, that the defendant distributed, dispensed and
caused to be distributed and dispensed the controlled
substances as charged; and [second], that at the time
of the distribution and dispensing, the defendant
knew that he was distributing and dispensing a con-
trolled substance not for a legitimate medical purpose
and not in the usual course of professional practice.
Doc. 392 at 181ā82. Immediately after, the district court told the
jury that ā[w]hether the defendant acted outside the usual course
of practice is to be judged objectively by reference to standards of
medical practice.ā Id. at 182. The court distinguished this question
from whether the defendant acted for a legitimate medical pur-
pose, which was to be judged āsubjective[ly].ā Id. The court also
gave a āgood faithā instruction. Id. at 177. Speciļ¬cally, it instructed
the jury that it could consider whether the defendantās āconduct
[was] in accordance with what the physician believe[d] to be proper
medical practiceā as a defense. Id. at 178. But the district court lim-
ited this defense to the Ā§ 846 conspiracy charge (because it had an
element of willfulness) and the ālegitimate medical purposeā
prong of the Ā§ 841 substantive counts. Id. at 177. It did not apply
this instruction to the usual course of professional practice prong
of the Ā§ 841 counts: the district court instructed the jury that it
must not consider āwhat [Santos] believe[d] to be proper medical
practice,ā id. at 178, under the usual course of professional practice
prong.
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20-13973 Opinion of the Court 27
Under our decisions in Ruan III and Heaton, this instruction
was error, and the error is plain. Greer, 141 S. Ct. at 2096. āAn error
is plain if it is obvious and clear under current law.ā United States v.
Johnson, 981 F.3d 1171, 1179 (11th Cir. 2020) (internal quotation
marks omitted). Current law for this purpose includes intervening
decisions: āan intervening decision by this Court or the Supreme
Court squarely on point may make an error plain.ā United States v.
Jones, 743 F.3d 826, 829ā30 (11th Cir. 2014) (internal quotation
marks omitted); see also Dell v. United States, 710 F.3d 1267, 1273
(11th Cir. 2013).
In Ruan III, we concluded that a district courtās jury instruc-
tion was error because it āinadequately conveyed the required
mens rea to authorize conviction under Ā§ 841(a).ā Ruan III, 56 F.4th
at 1298. Although the jury instruction in Ruan III conveyed that the
defendants had to act āknowingly and intentionallyā when they
ādispensed the controlled substance,ā it did not make clear that the
same requirement applied to the authorization prong. Id. at 1297.
That was so even though the jury instruction in Ruan III did not
state outright that ā[w]hether the defendant acted outside the usual
course of practice is to be judged objectively.ā Doc. 392 at 182. It
merely left open the possibility.
In Heaton, we confronted a jury instruction thatālike the
one the district court gave hereāstated that āwhether [the defend-
ant] dispensed the controlled substances outside the usual course
of professional practice is to be judged objectively.ā 59 F.4th at 1241
(internal quotation marks omitted). We concluded this instruction
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28 Opinion of the Court 20-13973
was error under Ruan II because āthis instruction allowed the jury
to convict [the defendant] without considering whether he know-
ingly or intentionally issued prescriptions outside the usual course
of professional practice.ā Id.
In sum, Ruan II holds that a defendant acts outside the āusual
course of professional practiceā under 21 U.S.C. Ā§ 841 only when a
knowing or intentional scienter requirement is satisļ¬ed. Ruan II.
142 S. Ct. at 2375. Applying that holding in Ruan III and Heaton, we
concluded that a district court errs by instructing a jury to āapply
an objective standard to the outside the usual course of profes-
sional practice requirement,ā Heaton, 59 F.4th at 1240 (internal quo-
tation marks omitted), or failing to āconvey that a subjective analy-
sis [is] required,ā Ruan III, 56 F.4th at 1297.
It is true that the district courtās instruction required the gov-
ernment to prove that Santos āknew that he was distributing and
dispensing a controlled substance not for a legitimate medical pur-
pose and not in the usual course of professional practice.ā Doc. 392
at 181ā82. But many other aspects of the instruction undercut the
idea that this knowledge requirement applied to the āusual course
of professional practiceā prong. Although the district court repeat-
edly clariļ¬ed that the jury had to consider Santosās subjective intent
to determine whether he acted without legitimate medical pur-
pose, it juxtaposed this requirement with an instruction that
ā[w]hether the defendant acted outside the usual course of practice
is to be judged objectively by reference to standards of medical
practice.ā Id. at 182. And it instructed the jury not to consider
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20-13973 Opinion of the Court 29
whether Santos acted in good faith when determining whether he
acted outside the usual course of practice. Taken as a whole, the
jury instructions failed to adequately convey that a defendant acts
outside the āusual course of professional practiceā under 21 U.S.C.
Ā§ 841 only when a knowing or intentional scienter requirement is
satisļ¬ed. See Christopher v. Cutter Labāys, 53 F.3d 1184, 1191 (11th Cir.
1995) (We āexamine[] jury instructions as a whole to determine
whether they fairly and adequately addressed the issue and cor-
rectly stated the law.ā) This failure is clearly and obviously (and thus
plainly) error under Ruan II, Ruan III, and Heaton. Johnson, 981 F.3d
at 1179.
Next, we consider whether the error aļ¬ected Santosās sub-
stantial rightsāthat is, whether there is āa reasonable probability
that, but for the error, the outcome of the proceeding would have
been diļ¬erent.ā Greer, 141 S. Ct. at 2096 (internal quotation marks
omitted). āA reasonable probability is a probability suļ¬cient to un-
dermine conļ¬dence in the outcome.ā Strickland v. Washington, 466
U.S. 668, 694(1984); see also United States v. Dominguez Benitez,542 U.S. 74
, 81ā82 (2004) (applying Stricklandās reasonable probability
prejudice standard to plain error review). A reasonable probability
is less than a preponderance. See Holland v. Jackson, 542 U.S. 649, 654
(2004). But if a ādefendantās guilt would have been clear under the
correct instruction, he loses under the substantial rights third prong
of plain error review.ā United States v. Iriele, 977 F.3d 1155, 1179
(11th Cir. 2020). Because we lack conļ¬dence that the outcome of
Santosās trial would have been the same on the Ā§ 841 counts but for
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30 Opinion of the Court 20-13973
the erroneous jury instruction, we conclude the error aļ¬ected San-
tosās substantial rights.
Consistent with our precedent, the district court instructed
the jury that it could consider whether a prescription was author-
ized based on disjunctive reading of the term not for a legitimate
medical purpose and not in the usual course of professional prac-
tice. See Heaton, 59 F.4th at 1239ā40; Doc. 392 at 183 (ā[I]f only one
of the alternatives is proved beyond a reasonable doubt, that is suf-
ļ¬cient for conviction . . . .ā). In other words, the jury was allowed
to convict Santos either because he wrote a prescription that was
not for a legitimate medical purpose or because it was not in the
usual course of professional practice; the jury did not need to ļ¬nd
both. As the government put it to the jury, āif you ļ¬nd that there
might have been a legitimate medical purpose to a prescription but
you think Dr. Duldulao or Dr. Santos still issued it outside the scope
of professional practice, they are guilty.ā Doc. 393 at 47. The juryās
verdict form did not specify which theory it relied on when it con-
victed Santos. So the jury could have rested its convictions solely
on an impermissible theory of liability: that Santosās actions did not
comply with objective professional norms of medicine. Under the
circumstances, we think this possibility is great enough to āunder-
mine conļ¬dence in the outcomeā of the trial. Strickland, 466 U.S. at
694.
Two principal reasons support our conclusion. First, the
governmentās trial presentation emphasized the theory that San-
tosās actions deviated from objective professional norms of
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20-13973 Opinion of the Court 31
medicine, giving the jury reason to convict Santos on an impermis-
sible theory of liability. Second, the juryās split verdict on the Ā§ 841
counts against Santos illustrates that the jury viewed this case as a
close callānot a slam dunk. C.f. Iriele, 977 F.3d at 1179 (a defend-
antās substantial rights are unaļ¬ected by instructional error if āthe
defendantās guilt would have been clear under the correct instruc-
tionā).
At trial, the government told the jury that āprescribing
within the scope of professional practice means within generally
accepted standards of medical practice, such as under Florida laws
or Federal Rules and regulations.ā Doc. 393 at 30. It put on an ex-
pert witness (Dr. Chaitoļ¬) to elaborate on those standards. And it
told the jury Santos transgressed them.
Over four days of testimony, Dr. Chaitoļ¬ outlined standards
that, in his opinion, constituted the relevant standards of medical
practice. For instance, Dr. Chaitoļ¬ told the jury that a doctor who,
āknowing that a patient is intentionally diverting,ā nevertheless āis-
sue[s] them a prescription for a controlled substanceā acts outside
āgenerally acceptable medical practice.ā Doc. 388 at 21. The same
is true, he opined, for a doctor who āexchange[s] . . . controlled sub-
stance for monetary remunerationā or violates rules contained in
āthe DEA manual 2006ā or āRule 64B8-9.013āāa provision of the
Florida Administrative Code requiring physicians who prescribe
controlled substances to manage pain to adopt practices including
adequate evaluation, periodic review, and thorough recordkeeping.
Id.; see also Fla. Admin. Code Ann. r. 64B8-9.013.
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32 Opinion of the Court 20-13973
Dr. Chaitoļ¬ also told the jury that Santos violated these
standards. He testiļ¬ed that ā100 percentā of Santosās patient ļ¬les
āfell below the standard of careā and that in āmost of them, pre-
scriptions for controlled substances . . . were not issued in the
course of . . . professional practice.ā Doc. 388 at 20. For example,
Dr. Chaitoļ¬ testiļ¬ed that when Santos ļ¬rst prescribed Chināthe
undercover agentācontrolled substances, he relied on āan inade-
quate history,ā and a āphysical examinationā that was āincom-
plete.ā Id. at 167. He testiļ¬ed that during Chin and Vasilasās ļ¬rst
joint visit to Santos (the basis for Santosās conviction on count seven
of the second superseding indictment), Santos prescribed con-
trolled substances āoutside the scope of professional practiceā be-
cause Santos failed to take a patient āhistory, [conduct a] complete
physical examination,ā consider āmedical necessityā or āother
medications,ā or address that the medication failed to improve Va-
silasās reported pain. Id. at 194. Dr. Chaitoļ¬ oļ¬ered similar opinions
on later visits Chin and Vasilas made to Santos. See, e.g., id. at 213
(āBased upon the lack of history, lack of physical examination, lack
of discussion of any alternative medical care . . . those medications
were prescribed . . . outside the practice of medicine.ā) (count
nine).
Dr. Chaitoļ¬ās testimony was the heart of the governmentās
trial presentation. As the government argued during trial, Dr.
Chaitoļ¬ās testimony was ācritical evidence for purposes of [its]
case-in-chief,ā and without Dr. Chaitoļ¬, the government would
struggle ā[i]n terms of being able to present [its] case.ā Id. at 86.
Indeed, after the district court struck the bulk of Dr. Chaitoļ¬ās
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20-13973 Opinion of the Court 33
testimony about Duldulao (but not Santos) for violating an in
limine order, it entered a judgment of acquittal on most of the sub-
stantive Ā§ 841 counts against Duldulao. Without Dr. Chaitoļ¬, that
aspect of the governmentās case failed. The jury also took copies of
some of the standards Chaitoļ¬ testiļ¬ed Santos violated into its de-
liberations. And in its closing arguments the government put these
standards in front of the jury and recounted how Santos violated
them, arguing ā[t]hat is not the practice of medicine. Thatās crimi-
nal.ā Doc. 393 at 115. In sum, the government presented its case in
a manner that encouraged the jury to convict Santos based on what
the Supreme Court has since clariļ¬ed is an improper view of the
scienter requirement under Ā§ 841.
Notwithstanding its trial presentation, the government ar-
gues that Santos loses on the substantial-rights prong of plain error
review because his guilt is clear, even under the correct jury instruc-
tion. See Iriele, 977 F.3d at 1179. The government relies on circum-
stantial evidence regarding the clinicās overall operations to argue
Santos acted knowingly. That misses the point. For the Ā§ 841
counts, the government obtained convictions based on Santosās
speciļ¬c interactions with patients on speciļ¬ed occasionsānot the
broader conspiracy or the misdeeds of the clinic. Ruan II means
that the government needed to show that Santos knew he was act-
ing in an unauthorized manner on each of these occasions, not that
he knew generally that the clinic was engaging in unlawful activity.
Recall that Santosās three substantive convictions (counts
seven, eight, and nine of the second superseding indictment) were
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34 Opinion of the Court 20-13973
based on a series of speciļ¬c visits with a DEA agent, Chin, and a
conļ¬dential informant posing as her boyfriend, Vasilas. Yet the jury
acquitted Santos of two counts of substantive violations of Ā§ 841
(counts ļ¬ve and six) based on Chinās earlier visits to Santos. The
jury convicted Santos on count seven based on prescriptions of ox-
ycodoneābut not the also-charged alprazolam (Xanax) prescrip-
tion. And the jury convicted Santos on counts eight and nine, based
on two later visits.
During each of the ļ¬ve visits underlying the indictment,
Santos ignored red ļ¬ags suggesting that Chin (and later Vasilas,
too) was engaged in drug-seeking behavior and potentially abusing
controlled substances. During the visit that the government
charged as count six, Chin told Santos she had been taking more
than the prescribed amount of oxycodone, traveling hundreds of
miles to HPC, and receiving opioids from multiple sources. Santos
responded by writing her a prescription for even more opioids.
During the visit that the government charged as count seven, San-
tos wrote another prescription for Chin even after Vasilas said Chin
had been taking pills from him.
But the jury did not respond to this evidence or the evidence
of the larger conspiracy by ļ¬nding that in each instance Santos vi-
olated the law: the jury acquitted on two counts, split on the third,
and convicted on two further counts. This split verdict demon-
strates that the jury did not infer from Santosā general knowledge
of the conspiracy that he knew the prescriptions he wrote were al-
ways for no legitimate medical purpose or always outside the usual
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20-13973 Opinion of the Court 35
course of professional practice. If the jury had drawn such an in-
ference, it would have convicted on counts ļ¬ve and six. This seri-
ously undercuts that governmentās reliance on the general evi-
dence of the conspiracyārather than evidence speciļ¬c to the dis-
crete prescriptions that underlie the Ā§ 841 countsāto argue that
Santos could not have suļ¬ered prejudice. The juryās split verdict
also suggests that the jury viewed each of the substantive counts as
a close call. As we have described, Santos repeatedly ignored red
ļ¬ags that Chin and Vasilas were abusing their prescriptions. But the
jury found that, across ļ¬ve charged visits with Chin and Vasilas,
Santos only sometimes crossed the criminal line drawn by Ā§ 841;
other times, he did not. The district courtās instructions to the jury
allowed it to draw that line short. Under these circumstances, the
district courtās instructional error āundermine[s] [our] conļ¬dence
in the outcomeā of the trial. Strickland, 466 U.S. at 694.
The fourth and ļ¬nal prong of plain error review requires us
to consider whether the error āseriously aļ¬ects the fairness, integ-
rity or public reputation of judicial proceedings.ā Olano, 507 U.S. at
736 (internal quotation marks omitted) (alteration adopted). This
error does.
In the context of sentencing errors, the Supreme Court has
explained that ā[t]he risk of unnecessary deprivation of liberty par-
ticularly undermines the fairness, integrity, or public reputation of
judicial proceedingsā when the court is responsible for the error.
Rosales-Mireles v. United States, 138 S. Ct. 1897, 1908 (2018). The re-
sponsibility is ours: over the last decades, we repeatedly, in
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36 Opinion of the Court 20-13973
published opinions, upheld jury instructions that misstated the
mens rea requirement under 21 U.S.C Ā§ 841. See, e.g., Tobin, 676 F.3d
at 1282ā83; Merrill, 513 F.3d at 1305; Williams, 445 F.3d at 1309ā10.
A jury then convicted Santos based in part on that misstatement.
Santos received a prison sentence on these counts, and āthe possi-
bility of additional jail time . . . warrants serious consideration in a
determination whether to exercise discretion under Rule 52(b).ā
Rosales-Mireles, 138 S. Ct. at 1907.
Ignoring this error would also undermine the policy inter-
ests the Supreme Court articulated in Ruan II. The Court empha-
sized that scienter requirements are fundamental to our criminal
law as the element that generally separates merely negligent con-
duct from conduct worthy of criminal punishment. Ruan II, 142 S.
Ct. at 2376ā77 (ā[C]onsciousness of wrongdoing is a principle as
universal and persistent in mature systems of criminal law as belief
in freedom of the human will and a consequent ability and duty of
the normal individual to choose between good and evilā (internal
quotation marks omitted) (alteration adopted)).
We will not run the risk that the jury transgressed that line.
We vacate Santos convictions under Ā§ 841ācounts seven, eight,
and nine of the second superseding indictment.
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20-13973 Opinion of the Court 37
C. Sufficiency of the Evidence
On remand, the parties again challenge the suļ¬ciency of the
evidence for the conspiracy counts under 21 U.S.C. Ā§ 846. 7 We
again ļ¬nd the evidence suļ¬cient.
A preserved challenge to the suļ¬ciency of the evidence re-
quires us to examine āwhether the evidence, when viewed in the
light most favorable to the government, and accepting reasonable
inferences and credibility choices by the fact-ļ¬nder, would enable
the trier of fact to ļ¬nd the defendant guilty beyond a reasonable
doubt.ā United States v. Monroe, 866 F.2d 1357, 1365 (11th Cir. 1989).
We will aļ¬rm a conviction unless there is āno reasonable construc-
tion of the evidenceā from which the jury could have found the
defendant guilty beyond a reasonable doubt. United States v. Garcia,
405 F.3d 1260, 1269 (11th Cir. 2005).
The government does not need direct evidence to prove con-
spiracy; circumstantial evidence can prove each element. The ļ¬rst
element, the existence of an agreement, āmay be proved by infer-
ences from the conduct of the alleged participants or from circum-
stantial evidence of a scheme.ā Azmat, 805 F.3d at 1035 (internal
quotation marks omitted). The second element, knowledge of an
agreement, is satisļ¬ed if āthe circumstances surrounding a personās
presence at the scene of conspiratorial activity are so obvious that
7 Santos does not challenge the sufficiency of the evidence for his substantive
convictions under Ā§ 841. We therefore do not address the issue.
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38 Opinion of the Court 20-13973
knowledge of its character can fairly be attributed to him.ā Id. (in-
ternal quotation marks omitted). As for the third element, that the
defendant voluntarily joined in the agreement, circumstantial evi-
dence can show a defendant participated in a conspiracy āby show-
ing that he committed acts that furthered the purpose of the con-
spiracy.ā United States v. Iriele, 977 F.3d 1155, 1172 (11th Cir. 2020).
Our cases sometimes merge the ļ¬rst two elements and abbreviate
the elements of conspiracy as āknowledgeā and āparticipation.ā
See, e.g., id. at 1169ā73.
Circumstantial evidence of conspiracy to distribute and dis-
pense controlled substances not for a legitimate medical purpose
and not in the usual course of professional practice includes āred
ļ¬agsā that would have put a reasonable doctor on notice of the il-
legitimacy of the operation. See, e.g., Azmat, 805 F.3d at 1036 (āAll
of the witnesses with medical backgrounds also testiļ¬ed that there
was an abundance of red ļ¬ags that should have tipped oļ¬ any doc-
tor that his patients were seeking pills.ā). Where, as here, the de-
fendant is a doctor who allegedly participated in a pill mill conspir-
acy, we have looked to evidence of the doctorās interaction with
patients to conclude āthat a defendant distributed a prescription
without a legitimate medical purpose and outside the usual course
of professional practice.ā Joseph, 709 F.3d at 1104. These aspects in-
clude inordinately large quantities of controlled substances pre-
scribed, brief or nonexistent physical examinations, failure to re-
view patient history before prescribing medications, issuance of
prescriptions to a patient known to be delivering the drugs to oth-
ers, and a lack of a logical relationship between the drugs
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20-13973 Opinion of the Court 39
prescribed and treatment of the allegedly existing condition. See id.;
Azmat, 805 F.3d at 1036.
Viewing the evidence in the light most favorable to the gov-
ernment, see Monroe, 866 F.2d at 1365, there were suļ¬cient red ļ¬ags
in evidence to establish the defendantsā knowledge of an unlawful
scheme. Combined with the evidence of the defendantsā own con-
duct, ample evidence showed that Duldulao and Santos knowingly
joined an agreement to unlawfully dispense controlled substances.
At the outset, we brieļ¬y address the relationship between
Ruan II and our analysis. As we explained in Ruan III, āa conviction
under Ā§ 846 requires the jury to ļ¬nd that the defendant[] knew of
the illegal nature of the scheme.ā Ruan III, 56 F.4th at 1299. In other
words, independent of the scienter requirement applicable to the
substantive oļ¬ense under Ā§ 841, our treatment of the elements of
a conspiracy under Ā§ 846 has always required the jury to ļ¬nd that
the defendant knew the object of the conspiracy was ādispensing a
controlled substance . . . in an unauthorized manner.ā Id. That is
why we previously considered whether the evidence was suļ¬cient
for a jury to conclude that both Duldulao and Santos knew of the
unlawful nature of the conspiracy they agreed to join: if the de-
fendants lacked subjective knowledge that the prescriptions were
unauthorized, they could not appreciate the unlawful nature of the
conspiracy. Thus, we restate much of our prior analysis, and we are
conļ¬dent that analysis remains correct following Ruan II.
1. Duldulaoās Suļ¬ciency Challenge
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40 Opinion of the Court 20-13973
Duldulao argues that there was insuļ¬cient evidence to sup-
port the elements of the conspiracy charge and, speciļ¬cally, that
the red-ļ¬ag evidence was weak. We agree with the district court
that there was suļ¬cient evidence for the jury to ļ¬nd that he know-
ingly joined an agreement to unlawfully dispense controlled sub-
stances. The district court relied on the following types of evi-
dence: HPC owner Ernest Gonzalezās testimony that Duldulao
agreed to write narcotics prescriptions; staļ¬ and patient testimony
about Duldulaoās adherence to the plan to write controlled sub-
stance prescriptions to most of the clinicās clientele; staļ¬ testimony
regarding HPCās operations while Duldulao served as Medical Di-
rector; patient testimony that conļ¬rmed the clinicās standard oper-
ating scheme under Duldulao; and Duldulaoās statements to his
then-girlfriend Kelly Schleisner about the clinic, including that it
was a āpain mill.ā Doc. 376 at 6ā9. This evidence was suļ¬cient to
establish that Duldulao knowingly and voluntarily joined an agree-
ment 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, we treat the ļ¬rst and sec-
ond elements, agreement to commit a crime and knowledge of the
agreement, as a single knowledge element here. The jury reasona-
bly could have inferred that Duldulao knew the criminal object of
the conspiracy based on Gonzalezās testimony about his interview
with Duldulao for the position of Medical Director, HPC staļ¬ās tes-
timony about Duldulaoās conduct at the clinic, staļ¬ and patient tes-
timony about the clinicās patients, and Duldulaoās statements to
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20-13973 Opinion of the Court 41
Schleisner. For the third element, voluntary participation, the jury
reasonably could have found from the testimony concerning his
conduct and interactions with patients that Duldulao willingly
agreed to and did participate in the conspiracy.
First, we turn to the knowledge element. Gonzalezās testi-
mony was evidence that Duldulao knew about the suspicious na-
ture of HPC from the beginning and nevertheless agreed to get
involved. During Duldulaoās job interview, Gonzalez showed him
a ļ¬le that listed the types of controlled substances HPC had previ-
ously prescribed for patients. Gonzalez told Duldulao that patient
visits were timed and that it was āexpected that he would probably
take about ten minutesā for each patient. Doc. 382 at 41. To āexpe-
dite things,ā the staļ¬ would write out prescriptions before the pa-
tientās visit that Duldulao could sign afterward. Id. at 41ā42. This is
circumstantial evidence of a scheme to get controlled substances
into patientsā hands as quickly as possible without regard to medi-
cal need. From this evidence, a jury could ļ¬nd that Duldulao
agreed to join the conspiracy when he agreed to prescribe opiates
under those conditions.
Besides what he knew before accepting his position as Med-
ical Director of HPC, in treating his patients Duldulao would have
seen that they exhibited signs of drug addiction, which are red ļ¬ags
for doctors. See Iriele, 977 F.3d at 1170; Azmat,805 F.3d at 1036
. Wit-
nesses described patients as looking like drug abusersāfor exam-
ple, they were āa little too sleepy,ā slurred their speech, had blood-
shot eyes or dilated pupils, had visible track marks, smelled of
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42 Opinion of the Court 20-13973
marijuana, and ānodd[ed] outā in the waiting room. Doc. 382 at 92,
96. One employee testiļ¬ed that some patients looked ālike they
were sleepy and like falling when they would walk.ā Doc. 382 at
155. Another described the waiting room as ā[s]ometimes chaosā
with āpeople nodding out.ā Doc. 384 at 100. One witness testiļ¬ed
that he was addicted to drugs while he was a patient at HPC and
looked like ādeath warmed over.ā Id. at 257. Nevertheless, he and
others like him left Duldulaoās oļ¬ce with prescriptions for opiates
and other controlled substances.
Beyond the patientsā appearances, Duldulao heard from
HPC staļ¬ that some patients had tested positive for illegal drugs.
Staļ¬ 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 ļ¬ags suggest the pa-
tients were seeking drugs without a legitimate medical purpose.
805 F.3d at 1036. Yet Duldulao prescribed them the drugs. A jury
could reasonably infer that he knew the patients were likely drug
abusers and knew that he was participating in a conspiracy to un-
lawfully prescribe controlled substances.
Other circumstances surrounding Duldulaoās presence at
HPC allowed a reasonable jury to attribute knowledge of the con-
spiracyās unlawful character to him. Duldulao knew that the clinicās
parking lot was covered with trash, including drug paraphernalia,
and that the clinic had little medical supplies or equipment. He
knew that the staļ¬ had no training for or experience with working
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20-13973 Opinion of the Court 43
in a medical oļ¬ce, yet they prewrote prescriptions for him to sign.
He knew that HPC did not accept insurance: patients could only
pay by cash or credit card. And he even told his girlfriend that he
worked at a āpain mill.ā Doc. 386 at 143. The jury therefore could
infer that he had āknowledge of the conspiracy due to his presence
atā the clinic. See Azmat, 805 F.3d at 1036.
Second, the element of active participation in the conspiracy
found support in the evidence of Duldulaoās conduct and interac-
tions with the patients. Some HPC patients testiļ¬ed that Duldulao
did not review their medical history forms and that his physical ex-
ams were as brief as two minutesāif they happened at all. See id.
Duldulao sometimes prescribed combinations of opioids, Xanax,
and Soma, drugs ādescribed in the . . . medical literature as the un-
holy holy trinity for substance abuse.ā Iriele, 977 F.3d at 1170 (inter-
nal quotation marks omitted). When he went on vacation,
Duldulao signed prewritten and postdated prescriptions and left
them with HPC staļ¬ so that patients could come in to pick them
up without a physician present or any medical exam. See Joseph, 709
F.3d at 1090ā91 (ā[E]very ālegitimate doctorā . . . knows that he may
not pre-sign prescriptions.ā). A jury could reasonably infer from
this conduct that Duldulao actively participated in the conspiracy.
Duldulao argues that this evidence was insuļ¬cient 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 Duldulaoās agreement to exclusively write prescrip-
tions for controlled substances, or that the patients would not have
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44 Opinion of the Court 20-13973
a medical need for these drugs. And, despite his own guilty plea,
Gonzalez testiļ¬ed that he ā[n]everā conspired āwith Dr. Duldulao
to have him write scripts for no legitimate medical purpose.ā Doc.
383 at 214. But the jury was free to believe parts of Gonzalezās tes-
timony and disregard others. See United States v. Takhalov, 827 F.3d
1307, 1321 n.10 (11th Cir. 2016). Thus, the jury reasonably could
have found that Duldulao did, in fact, agree to and participate in
the conspiracy to unlawfully distribute controlled substances.
Duldulao is correct that the jury heard countervailing evi-
dence. For instance, videos of undercover oļ¬cersā appointments
with Duldulao showed him asking about their medical history and
performing a physical exam. In these videos, he asked about their
current medications and advised them not to mix the opiates with
alcohol. But Duldulaoās then-girlfriend Schleisner testiļ¬ed that he
told her that he was āpretty sureā some patients were undercover
oļ¬cers. Doc. 386 at 132. Construing the evidence in the govern-
mentās favor, as we must, we conclude that a reasonable jury could
have found that these recorded exams were anomalies based on
Duldulaoās suspicions that he was dealing with undercover law en-
forcement and that most of the time he adhered to the agreement
to write prescriptions for controlled substances for no legitimate
medical purpose and outside the usual course of professional prac-
tice.
Duldulao also argues that his conspiracy conviction cannot
stand because he was acquitted of the underlying substantive
charges. Not so. Juries sometimes render inconsistent verdicts;
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20-13973 Opinion of the Court 45
inconsistency alone is not a suļ¬cient reason for setting the verdict
aside. See United States v. Powell, 469 U.S. 57, 64ā65 (1984). We have
upheld a defendantās conviction where he was found guilty of con-
spiracy only and not the underlying substantive oļ¬enses. United
States v. Brito, 721 F.2d 743, 749ā50 (11th Cir. 1983) (ā[I]nconsistency
in a juryās verdict does not require reversal.ā). ā[A]s long as the
guilty verdict is supported by suļ¬cient evidence, it must stand,
even in the face of an inconsistent verdict on another count.ā United
States v. Mitchell, 146 F.3d 1338, 1345 (11th Cir. 1998). Having exam-
ined the evidence that supports Duldulaoās conspiracy conviction
and found it to be suļ¬cient, we reject this challenge and aļ¬rm the
district court.
And, in any event, the juryās verdict was not inconsistent.
The Ā§ 841 charge on which the jury acquitted Duldulao required
the jury to ļ¬nd that Duldulao knowingly distributed a controlled
substance in an unauthorized manner on a particular occasion. The
jury was reasonably able to ļ¬nd thatābased on the evidence at
trialāthe government had not shown beyond a reasonable doubt
that Duldulao violated Ā§ 841 on that occasion but had nevertheless
knowingly joined a conspiracy to unlawfully distribute controlled
substances in the abstract and on other occasions.
2. Santosās Suļ¬ciency Challenge
Turning to Santos, we agree with the district court that there
was suļ¬cient evidence to support the juryās ļ¬nding that he know-
ingly joined an agreement to unlawfully dispense controlled sub-
stances. The district court relied on the following types of
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46 Opinion of the Court 20-13973
evidence: Gonzalezās testimony, including his admission that
ā[t]hatās what Iām pleading to,ā Doc. 383 at 224, when asked on
cross examination whether he conspired with Santos; staļ¬ and pa-
tient testimony about Santosās conduct and interactions with pa-
tients; staļ¬ testimony about HPCās operations while Santos served
as Medical Director, which included brief, timed patient visits, pre-
written prescriptions, little to no medical equipment, and no expe-
rienced staļ¬ers; patient testimony about their experiences, con-
ļ¬rming that the clinicās standard operating scheme under Santos
featured āhigh patient volume, long-distance patients, brief medi-
cal visits, little to no medical documentation needed to see the doc-
tor, cash payments, no insurance, cursory physical examinations,
papered and/or inaccurate patient records, and patients presenting
with signs of apparent drug abuse.ā Doc. 377 at 8. 8 This evidence
was suļ¬cient to establish that Santos knowingly and voluntarily
8 The district court also relied on another piece of evidence: Santosās testi-
mony admitting that he agreed to write prescriptions for controlled substances
at HPC, despite the many indicators that it was not a legitimate operation. We
agree with Santos that the district court erred when it relied on his testimony.
When a district court reserves ruling on a motion for a judgment of acquittal
made after the governmentās case-in-chief, the district courtās analysis of the
evidence and our review on appeal is limited to the evidence the government
presented. United States v. Moore, 504 F.3d 1345, 1346 (11th Cir. 2007). Because
Santos moved for a judgment of acquittal at the close of the governmentās
evidence, the district court had to follow this snapshot rule and judge the suf-
ficiency of the evidence based only on the governmentās case. But this is harm-
less error; the remaining evidence was sufficient to deny the motion and con-
vict Santos. See Barton, 909 F.3d at 1337.
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20-13973 Opinion of the Court 47
joined an agreement to unlawfully distribute controlled sub-
stances.
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 requirement. We
agree with the district court that there was suļ¬cient evidence to
support the juryās ļ¬nding that Santos knowingly joined an agree-
ment to unlawfully dispense controlled substances. Gonzalezās tes-
timony shows that Santos knew about the suspicious circum-
stances at HPC. Santosās tenure at HPC featured the same red ļ¬ags
that support Duldulaoās conspiracy conviction.
Gonzalezās testimony was evidence that Santos knew he was
agreeing to work at a clinic with an unlawful criminal purpose.
When Gonzalez interviewed Santos for the Medical Director posi-
tion, he made it clear that he wanted a doctor who would write
controlled substance prescriptions because when ā[t]he patients
would come in, they wanted their controlled substances.ā Doc. 383
at 67. Just like he did with Duldulao, Gonzalez showed Santos a ļ¬le
that contained the types of drugs HPC had prescribed. Santos āwas
okay with all of it except for he didnāt like the methadone and the
Xanaxes together.ā Id. Gonzalez notiļ¬ed Santos of the āsame for-
matā for timed visits as he had done with Duldulao, and Santos
agreed to write prescriptions under those conditions. Id. at 68. San-
tosās job interview presented circumstantial evidence that he knew
about the criminal scheme.
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48 Opinion of the Court 20-13973
Other circumstantial evidence about HPC supported an in-
ference that Santos knew about and agreed to the conspiracy. This
evidence included many red ļ¬ags, which we discussed as to
Duldulao and which āall stayed the sameā under Santos: the oļ¬ce
had minimal medical equipment or supplies; the staļ¬ was un-
trained; patients traveled long distances to the clinic; the parking
lot was littered with trash, including syringes; and HPC only ac-
cepted cash or credit cardānot insurance. Doc. 384 at 117ā18. Pa-
tients showed signs of drug addiction, including slurred speech,
ānodding out,ā and track marks on their arms. Doc. 383 at 113. Re-
gardless, āthey got their medicationsā from Santos. Id. 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 Santosās conduct. Santos, like Duldulao, signed and postdated
prescriptions when he went on vacations. Patients did not see San-
tos while he was on vacation, but they came to HPC and picked up
their postdated prescriptions nonetheless. Santos also left blank,
pre-signed prescriptions for HPC staļ¬ to issue. His conduct sup-
ported an inference that he knew he had agreed to participate in
the conspiracy to unlawfully distribute controlled substances.
Further, at one point, Santos came into the clinic āreal nerv-
ousā and told Gonzalez āthat [they] had to start dropping the med-
icationsā to lower doses. Id. at 125. Gonzalez responded that pa-
tients who had been taking high doses could not simply decrease
their doses overnight; they could suļ¬er a heart attack or a seizure.
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20-13973 Opinion of the Court 49
Santos began lowering prescription doses anyway, telling Gonzalez
there were new guidelines from the federal government to comply
with. In fact, the Drug Enforcement Administration (DEA) had re-
cently seized patient records and shut down a clinic Santosās wife
operated. The jury could have inferred that Santos was worried
that the DEA would raid HPC and discover that he had been pre-
scribing abnormally high doses of controlled substances. See Az-
mat, 805 F.3d at 1028, 1036ā37 (upholding the conviction of a doc-
tor who sometimes decreased patientsā medications for self-serving
reasons).
Although we vacate Santosās Ā§ 841 convictions that were
based on his interactions with purported patients who were actu-
ally government agents, the circumstances surrounding those visits
gave additional inferential support to the ļ¬nding that Santos knew
of the unlawful conspiracy.9 An undercover video with conļ¬dential
9 We note the different standards of review for determining whether to vacate
these convictions based on the erroneous jury instructions and whether the
evidence was sufficient. We vacate these convictions because we lack confi-
dence that the jury would have reached the same outcome but for the district
courtās erroneous jury instructions regarding the scienter requirement of
Ā§ 841. But here, assessing the sufficiency of the evidence underlying Santosās
Ā§ 846 conviction, we view all the evidence in the light most favorable to the
government and ask whether there is any āreasonable construction of the ev-
idenceā from which the jury could have found the defendant guilty. Garcia,
405 F.3d at 1269. The evidence of Santosās conductārepeatedly ignoring red
flags suggesting Chin and Vasilas were abusing controlled substances and writ-
ing them prescriptions anywayāunderlying counts five through nine could
reasonably be construed to support the inference that Santos knowingly
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50 Opinion of the Court 20-13973
informant Vasilas showed that when Santos asked how Vasilasās
supply of narcotics had held up in the months since his last visit,
Vasilas said, āI know that Iām not supposed to be saying this but I
had to ask friends and family, you know, to help me out.ā Doc. 372-
213 at 2:30ā2:50. Santos gave him prescriptions anywayāin fact,
Santos gave him three monthsā worth of prescriptions, made him
pay three times as though he were coming back in for two follow-
ups, and let his girlfriend pick up his prescriptions, even though Va-
silas had just admitted to sharing medication. When Chin asked for
an increase in her dosage, Vasilas told Santos āI know weāre not
supposed to talk about this, doc, but, you know, . . . she runs out
because itās not enough for her, so I have to help her out some-
times.ā Id. at 15:30ā15:38. These admissions showed that the pa-
tients were diverting their medication, a serious red ļ¬ag that sug-
gested 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 increased quantities they wanted.
Santos contends that āpatient testimony and resort to red
ļ¬ags cannot mend the evidentiary gap [as to an agreement] be-
cause it does not show any agreement between Dr. Santos and
Gonzalez.ā Santos Appellantās Br. at 54. We disagree. Just as with
Duldulao, the jury was entitled to rely on āinferences from the con-
duct of the alleged participants or from circumstantial evidence of
participated in a conspiracy to distribute controlled substances without au-
thorization. So this conduct remains relevant to a sufficiency analysis notwith-
standing our conclusion that his Ā§ 841 convictions cannot stand after Ruan II.
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20-13973 Opinion of the Court 51
[the] schemeā to ļ¬nd an agreement. Azmat, 805 F.3d at 1035 (inter-
nal quotation marks omitted). Gonzalezās testimony, the multiple
red ļ¬ags, and Santosās conduct together constitute suļ¬cient evi-
dence that Santos agreed to work at a pill mill and unlawfully dis-
tribute controlled substances. A reasonable jury could ļ¬nd from
this evidence that Santos agreed to be part of a conspiracy to dis-
tribute controlled substances with no legitimate medical purpose
and outside the scope of professional practice. We reject his chal-
lenge to the suļ¬ciency of the evidence supporting his conspiracy
conviction.
D. Dr. Chaitoffās Expert Testimony
To meet its burden of proving that a doctor knowingly is-
sued prescriptions with no legitimate medical purpose or outside
the usual course of professional practice, the government often
uses the testimony of a medical expert witness to help satisfy its
burden. See, e.g., Azmat, 805 F.3d at 1036. But we have also held
that expert medical testimony is unnecessary for a conviction. Jo-
seph, 709 F.3d at 1100. In this case, the government called an expert
witness, Dr. Chaitoff, who testified about the definitions of ālegiti-
mate medical purposeā and āthe usual course of professional prac-
tice.ā
Although Santos failed to raise these objections before the
district court, he argues to us now that Dr. Chaitoffās testimony
violated the rules of evidence in two ways: first, by opining on San-
tosās subjective mental state, and second, by reaching a legal con-
clusion. Reviewing Santosās arguments under the standard of plain
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52 Opinion of the Court 20-13973
error, we conclude the district courtās decision to admit the testi-
mony was not contrary to binding precedent directly resolving
these legal issues. United States v. LejardeāRada, 319 F.3d 1288, 1291
(11th Cir. 2003). Therefore, we discern no plain error.
A district court may admit expert testimony that āhelp[s] the
trier of fact to understand the evidence or to determine a fact in
issue.ā Fed. R. Evid. 702(a). Generally, ā[a]n opinion is not objec-
tionable just because it embraces an ultimate issue.ā Fed. R. Evid.
704(a). But ā[i]n a criminal case, an expert witness must not state
an opinion about whether the defendant did or did not have a men-
tal state or condition that constitutes an element of the crime
charged or of a defense. Those matters are for the trier of fact
alone.ā Fed. R. Evid. 704(b). Rule 704 bars a witness from giving
legal opinions (e.g., āthe defendant broke the lawā) and from dis-
cussing culpable mental states (e.g., āand he did it knowinglyā). An
expert witness can give his opinion about an ultimate issue so long
as he does not tell the jury what result to reach. See Fed. R. Evid.
704 advisory committeeās note. There is a difference between opin-
ing 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).
We reject Santosās first argumentāthat Dr. Chaitoffās testi-
mony violated Federal Rule of Evidence 704(b) and impermissibly
opined on Santosās subjective mental stateābecause it is unsup-
ported by the record. Although Dr. Chaitoff testified about Santosās
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20-13973 Opinion of the Court 53
conduct and his professional opinion of that conduct, he did not
speculate about what was going on in Santosās mind.
Santos also fails to show that it was plain error to admit Dr.
Chaitoffās testimony even though the testimony reached the ulti-
mate issue of whether Santos prescribed drugs for no legitimate
medical purpose and outside the usual course of professional prac-
ticeāthe standards of medical care relevant here. See 21 C.F.R. Ā§
1306.04(a). To summarize Dr. Chaitoffās testimony, 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 practice. Giving exam-
ples from his experience, he explained the process he follows before
prescribing controlled substances as follows: finding out who re-
ferred the patient; verifying that the patient has insurance; detailing
the patientās pain complaints and medical and social history, touch-
ing on whether there is a history of substance abuse; and complet-
ing an extensive physical examination. Before starting a patient on
controlled substances, he discusses the medicationās risks and coun-
sels the patient about alternative pain management treatments. He
emphasized that there is no one-size-fits-all approach to treating a
patientās pain.
He also testified about red flags that would warn him that
patients might be abusing their medication: patients with no med-
ical records or no referral, those who traveled long distances, and
those who shared their medication or ran out early. These are all
examples of patients who would prompt further investigation,
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54 Opinion of the Court 20-13973
according to Dr. Chaitoff. He found red flags when he watched vid-
eos of undercover officer Chin and confidential informant Vasilas
visiting Santosās office. Santos had prescribed opiates to Chin for
four months. She then 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 withdrawal.
Dr. Chaitoff also noted that it is unusual for a doctor to see
a couple together and perform a brief physical exam on both sim-
ultaneously, as Santos did in the video. Reviewing Santosās notes,
Dr. Chaitoff testified that there was little documentation about the
results of the physical examinations and why the injuries warranted
treatment with controlled substances. Strikingly, 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 ulti-
mate issue when he testified that, at that visit, 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 the pairās two other visits.
Although we vacate Santosās convictions under Ā§ 841 based
on those three patient visits, the jury also considered Dr. Chaitoffās
testimony when it convicted Santos on the Ā§ 846 conspiracy
charge, a conviction we affirm. It was not plain error to admit Dr.
Chaitoffās ultimate-issue evidence. Our precedent allows medical
experts to testify about the ultimate issue of the appropriate
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20-13973 Opinion of the Court 55
standard of care. In Azmat, the governmentās medical expert testi-
fied that the patients exhibited an āabundance of red flagsā and
opined that the doctor did not write prescriptions for them for a
legitimate medical purpose or in the usual course of professional
practice. 805 F.3d at 1036. The defenseās medical expert concluded
that the doctor āact[ed] appropriately under medical standards,ā
but the jury determined that the governmentās expert was more
credible and convicted the defendant. Id. We accepted both ex-
pertsā testimony as properly admitted and affirmed the doctorās
conviction. See id. at 1042ā44, 1049. Just like in Azmat, it was not
plain error here for the district court to admit Dr. Chaitoffās testi-
mony for the juryās consideration.
Ruan II does not undermine that conclusion. As Santos con-
cedes, Ruan II āleft the door ajar about how to prove mens rea.ā
Supp. Br. of Appellant Santos at 13. But a finding of plain error must
be justified by on-point authority. LejardeāRada, 319 F.3d at 1291. If
anything, Ruan II weakens an ultimate-issue objection to testimony
of the kind offered by Dr. Chaitoff. Ruan II makes clear that the
mere fact a doctor acts outside the course of professional practice
or without a legitimate medical purpose does not suffice for a con-
viction under Ā§ 841: āthe Government must prove beyond a rea-
sonable doubt that the defendant knew that he or she was acting in
an unauthorized manner, or intended to do so.ā Ruan II, 142 S. Ct.
at 2375. Thus, post-Ruan II, a jury that accepted Dr. Chaitoffās tes-
timony as true would not be required to convict. So Ruan II dis-
tances a medical expertās opinion on whether a doctor acted with-
out a legitimate medical purpose or outside the course of
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56 Opinion of the Court 20-13973
professional practice from the question of guilt under Ā§ 841. Santos
cannot show plain error.
E. Santosās Motion to Strike Dr. Chaitoffās Testimony
During trial, Dr. Chaitoff offered basically two types of tes-
timony: first, he explained the medical and regulatory standards
that govern the prescription of controlled substances, and second,
he offered his opinion on whether Duldulaoās and Santosās conduct
conformed to those standards. During trial, a problem emerged. In
forming his opinion about Duldulao, Dr. Chaitoff had relied on ma-
terial relating to Duldulaoās activities at a second pain clinic and
alleged pill mill that the district court excluded from evidence after
granting a motion in limine. Dr. Chaitoffās reliance on these ex-
cluded materials put Duldulao in a bind. He could not fully cross-
examine Dr. Chaitoff on the basis for his opinion without also dis-
cussing material the district court excluded. Duldulao and Santos
both moved to strike Dr. Chaitoffās testimony. The district court
granted Duldulaoās motion in part, striking Dr. Chaitoffās testi-
mony regarding Duldulaoās conduct but not his testimony regard-
ing the general standard of care nor his testimony regarding Santos,
about whom Dr. Chaitoff had not considered excluded evidence.
Santos argues the district court abused its discretion by not
striking Dr. Chaitoffās testimony about him, too. We disagree. Alt-
hough the court deemed Dr. Chaitoff a āless than reliable witnessā
because of his memory problems and lack of candor, it was within
the courtās discretion to deny Santosās motion to strike. Doc. 388
at 97. Only one topic was off-limits in Santosās cross-examination:
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20-13973 Opinion of the Court 57
the evidence about Duldulaoās other pain clinic that the courtās in
limine order excluded. That limit did not substantially affect San-
tosās right to cross-examine the witness; Dr. Chaitoff had not relied
on the excluded evidence in forming his opinions about Santos and
the general standard of care, and Santos could mitigate any preju-
dice from Dr. Chaitoffās other shortcomings through thorough
cross-examination. See United States v. Williams, 865 F.3d 1328, 1341
(11th Cir. 2017).
F. Santosās Sentence
Santos previously challenged his sentence, and we aļ¬rmed.
On remand, we need not reconsider the merits of his arguments in
light of Ruan II. Because we vacate Santosās convictions on counts
seven, eight, and nine, we vacate his sentence, too. See United States
v. Fowler, 749 F.3d 1010, 1015ā16 (11th Cir. 2014) (explaining that,
on direct appeal, āwe have routinely, without hesitation and as a
matter of course, vacated entire sentences and remanded for resen-
tencing on all surviving counts after vacating a conviction or sen-
tence on some, but not all, of the countsā because a āmulticount
sentence is a packageā (internal quotation marks omitted)).
IV. CONCLUSION
For the above reasons, we AFFIRM Duldulaoās conviction
on count one of the second superseding indictment. We AFFIRM
Santosās conviction on count one, VACATE Santosās convictions on
counts seven, eight, and nine, VACATE Santosās sentence,
REMAND for resentencing, and REMAND for a new trial on
counts seven, eight, and nine.