United States v. Kendrick Eugene DuldulaoUnited States v. Kendrick Eugene Duldulao
*2 Before J ORDAN , J ILL P RYOR , and T JOFLAT , Circuit Judges.
J ILL P RYOR , 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 “pill mill,” the Supreme
Court vacated our judgment and remanded for further considera-
tion in light of
Ruan v. United States
,
I. BACKGROUND
This appeal concerns the criminal convictions of two doc-
tors, Duldulao and Santos, who participated in a “pill mill”—a pain
management clinic that does not follow medical standards because
its purpose is to prescribe controlled substances regardless of
whether its patients have a medical need for them.
See United States
v. Azmat
,
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 “were coming in [] to get controlled substances,” so, at Duldulao’s and Santos’s respective job interviews, Gonzalez made it clear that HPC’s patients expected to receive controlled sub- stances during their visits. Doc. 382 at 38. 1 Gonzalez confirmed that Duldalao knew the clinic “need[ed] a doctor who was going to do controlled substances” and discussed specific controlled sub- stances that Duldulao would use to treat the clinic’s 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 (30–40 patients per day); and up-front payment only—HPC did not accept insurance.
Other characteristics suggested that the clinic was not a le- gitimate medical operation. The clinic had barely any medical equipment—only an exam table for the patients to sit on—or 1 “Doc.” refers to the district court’s docket entries.
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- tient’s brief visit.
HPC’s 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 withdrawal— sweating, shaking, vomiting, and experiencing hot and cold flashes. People were “nodding out” in the waiting room and “shooting up” in the parking lot. Doc. 384 at 100; Doc. 387 at 42. Patients hung out in the parking lot and left 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 management—just an MRI within the last two years documenting a physical abnormality of some kind. That and a Florida driver’s *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 distances—both red flags for controlled sub- stance abuse, according to the government’s 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 “pain mill.” Doc. 386 at 143.
When Santos replaced Duldulao as HPC’s 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 patient’s medical history or drug test was missing. It did not matter if a patient told him she shared her pills with friends or family. He prescribed patients controlled substances nonetheless. He pre- scribed drugs in the same dangerous combinations that Duldulao *6 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 “boyfriend,” 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 Santos’s 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 DEA’s “pro- hibition” on controlled substances resulting in the closure of many pain clinics. Doc. 372-208 at 4:30–5:10. 2 And Chin used slang (“30s” and “15s” of “Oxy”) to describe quantities and types of controlled substances, suggesting a potential substance-abuse problem. Id . at 5:10–5:20. 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 government’s trial exhibit list) refer to these videos by their exhibit numbers.
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 because—although she ex- perienced no increase in pain—she had been “doubling,” taking more than the prescribed amount. Doc. 372-212 at 11:00–12:15. 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 0:42–0:44 (“In Alabama I’m gettin’ em.”). And Chin revealed that she lived in Panama City, meaning she travelled al- most 400 miles to HPC’s 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 Chin’s next visit, Vasilas came with her. Vasilas, a return- ing patient, told Santos that Chin was “robbing” him of his pills when she ran out of hers. Doc. 386 at 173. Instead of investigating this red flag, Santos gave 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 *8 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 Vasilas’s 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 “do not fill un- til” 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 testified 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
At trial, the government established the facts surrounding Duldulao’s and Santos’s conduct through the testimony of Gonza- lez, government agents, HPC patients, and HPC employees. The government also called Dr. Chaitoff as an expert in pain manage- ment treatment. Dr. Chaitoff testified about how he practices pain management, underscoring how it differs from the conduct of the doctors and staff of HPC. In his practice, Dr. Chaitoff 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-up—much longer than the appointments patients received with Duldulao or Santos. He testified that patients who are clearly abusing controlled substances should not be treated with more controlled substances, even if they have a legitimate pain problem.
Dr. Chaitoff also opined that “most of” the prescriptions that Santos wrote for controlled substances “were provided for no le- gitimate medical purpose, [and] they were not issued in the course of one’s professional practice.” Doc. 388 at 20. Santos moved to strike his testimony, but the district court denied the motion, *10 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 trial’s conclusion, the district court granted Duldulao’s 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
Duldulao and Santos appealed on four grounds. Both men
challenged the sufficiency of the evidence as to their conspiracy
convictions under
After we affirmed, the Supreme Court addressed liability un-
der
Title 21
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
Ruan II
rejected that distinction. Overruling our decision in
United States v. Ruan
,
After we affirmed Santos’s 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 “[t]he judgment.” Judg-
ment,
Santos v. United States
,
II. STANDARD OF REVIEW
“We 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.”
Azmat
,
In a criminal appeal, we review issues not raised at trial for
plain error, which “occurs if (1) there was error, (2) that was plain,
(3) that affected the defendant’s substantial rights, and (4) that seri-
ously affected the fairness, integrity, or public reputation of judicial
proceedings.”
United States v. Wright
,
We review the district court’s 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 defendant’s substantial rights.
See United
States v. Barton
,
4 Decisions of the Fifth Circuit issued before October 1, 1981 are binding prec-
edent in this circuit.
Bonner v. City of Prichard
,
We review a district court’s application of the Sentencing Guidelines de novo . United States v. Johnson , 980 F.3d 1364, 1374 (11th Cir. 2020).
III. DISCUSSION On remand, Duldulao and Santos renew the challenges we addressed in our now-vacated opinion affirming their convictions and Santos’s 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 § 846 con- spiracy counts and the § 841 substantive counts failed to convey the mens rea Ruan II requires. We conclude that only the challenge to the § 841 jury instructions has merit. We therefore affirm Duldulao’s conviction under § 846, affirm Santos’s conviction un- der § 846, vacate Santos’s convictions under § 841, and vacate San- tos’s sentence.
A. § 846 Jury Instructions
The jury convicted both Duldulao and Santos of conspiracy
to distribute and dispense controlled substances without authori-
zation, violating
Invited or not, our decision on remand in
United States v.
Ruan
,
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 *16 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 “willfully means that the act was committed voluntarily and purposely, with the in- tent to do something the law forbids.” 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 briefs—filed after Ruan III — 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 “[t]he in- structions in Ruan and this case aren’t different in any material re- spect.” Santos Supp. Reply Br. at 6. Instead, they contend that Ruan III either flunks 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, 1256–57 (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 “first [panel] in this Circuit to address [an] issue.”
Smith v.
GTE Corp.
,
Duldulao and Santos also try to direct us to
United States v.
High
,
High
’s holding rested on our conclusion that the conspiracy
instruction did not cure the erroneous instruction as to the conspir-
acy’s 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
5 Because we conclude Ruan III is the controlling prior panel precedent, we need not consider whether—as the government argues—intervening Su- preme Court precedent has abrogated High ’s remedial holding.
Ruan III
controls and requires us to conclude that the instruc-
tions the jury received describing the elements of a conspiracy un-
der
B. § 841 Jury Instructions
Besides one count of
Under the doctrine of invited error, on appeal, “a party may
not challenge as error a ruling or other trial proceeding invited by
that party.”
Ford ex rel. Estate of Ford v. Garcia
,
The doctrine of invited error applies when an error is “at-
tributable to the action of the defense.”
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 “in-
troducing error at trial with the intention of creating grounds for
reversal on appeal.”
United States v. Stone
,
Considering the doctrine’s purposes, our sister circuits rec-
ognize an exception where the “error” invited by a party “relied on
settled law that changed while the case was on appeal.”
United
States v. Titties
, 852 F.3d 1257, 1264 n.5 (10th Cir. 2017);
see also
United States v. Andrews
,
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
,
The government’s position diverges as well from broader
principles governing our review. In this criminal appeal, applying
the doctrine would undermine the principle that “[d]ecisions of the
Supreme Court construing substantive federal criminal statutes
must be given retroactive effect.”
United States v. Peter
,
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
*23
Bivens Garden Off. Bldg., Inc. v. Barnett Bank of Fla., Inc.
, 906 F.2d
1546, 1554 (11th Cir. 1990) (adopting one accrual rule),
with Rotella
v. Wood
,
Against that backdrop, the defendants in
Maiz
raised the
four-year limitations period for civil RICO claims as an affirmative
defense.
The defendants argued that invited error does not apply when a jury “instruction is rendered incorrect by an intervening change in the governing law” and that “ Rotella [was] such a change in the law.” Id . at 677. We did not reject such a rule outright; rather, we determined that Maiz was not “an appropriate [case] to carve out an exception to the invited error rule.” Id . We noted that the defendants in Maiz had not shown “that the district court’s instruc- tion was probably responsible for an incorrect verdict.” Id . (internal quotation marks omitted). And the defendants had not shown that *24 theirs was the “exceptional” civil case justifying reversal on plain error review. Id . We also observed that the defendants in Maiz “had reasonable grounds for declining to propose—and, if necessary, stating an objection to—the [accrual] instruction that instead they asked the court to give.” 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 offense. And, as we conclude below, on this case’s 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- cause—as the government noted in its proposed jury instruc- tions—it 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 case—a criminal appeal involving an instructional error in defining a substantive offense flowing directly from our long- standing and clear precedent and attributable to both parties—we will not invoke the doctrine.
Because we reject the government’s invitation to apply the
doctrine of invited error, we instead review the district court’s jury
instructions for plain error. 6
See Greer v. United States
, 141 S. Ct.
2090, 2096 (2021). A defendant bears the “burden of establishing
entitlement to relief for plain error.”
Id
. at 2097 (internal quotation
marks omitted). To do so, a defendant must show four things:
“First, there must be an error. Second, the error must be plain.
Third, the error must affect 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 different.”
Id
. at 2096 (internal quotation marks and emphasis omitted).
Fourth—if a defendant makes these first three showings—we con-
sider whether the error “seriously affects the fairness, integrity or
public reputation of judicial proceedings.”
United States v. Olano
,
Taking the first two showings together, the district court’s 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.
to obtain a conviction under
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 181–82. Immediately after, the district court told the
jury that “[w]hether the defendant acted outside the usual course
of practice is to be judged objectively by reference to standards of
medical practice.”
Id
. at 182. The court distinguished this question
from whether the defendant acted for a legitimate medical pur-
pose, which was to be judged “subjective[ly].”
Id
. The court also
gave a “good faith” instruction.
Id.
at 177. Specifically, it instructed
the jury that it could consider whether the defendant’s “conduct
[was] in accordance with what the physician believe[d] to be proper
medical practice” as a defense.
Id
. at 178. But the district court lim-
ited this defense to the
Under our decisions in
Ruan III
and
Heaton
, this instruction
was error, and the error is plain.
Greer
,
In
Ruan III
, we concluded that a district court’s jury instruc-
tion was error because it “inadequately conveyed the required
mens rea to authorize conviction under
In
Heaton
, we confronted a jury instruction that—like the
one the district court gave here—stated that “whether [the defend-
ant] dispensed the controlled substances outside the usual course
of professional practice is to be judged objectively.”
In sum,
Ruan II
holds that a defendant acts outside the “usual
course of professional practice” under
It is true that the district court’s instruction required the gov-
ernment to prove that Santos “knew 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.” Doc. 392
at 181–82. But many other aspects of the instruction undercut the
idea that this knowledge requirement applied to the “usual course
of professional practice” prong. Although the district court repeat-
edly clarified that the jury had to consider Santos’s subjective intent
to determine whether he acted without legitimate medical pur-
pose, it juxtaposed this requirement with an instruction that
“[w]hether the defendant acted outside the usual course of practice
is to be judged objectively by reference to standards of medical
practice.”
Id
. at 182. And it instructed the jury not to consider
*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 “usual course of professional practice” under
Next, we consider whether the error affected Santos’s sub-
stantial rights—that is, whether there is “a reasonable probability
that, but for the error, the outcome of the proceeding would have
been different.”
Greer
,
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
,
Two principal reasons support our conclusion. First, the
government’s trial presentation emphasized the theory that San-
tos’s actions deviated from objective professional norms of
*31
medicine, giving the jury reason to convict Santos on an impermis-
sible theory of liability. Second, the jury’s split verdict on the
At trial, the government told the jury that “prescribing within the scope of professional practice means within generally accepted standards of medical practice, such as under Florida laws or Federal Rules and regulations.” Doc. 393 at 30. It put on an ex- pert witness (Dr. Chaitoff) to elaborate on those standards. And it told the jury Santos transgressed them.
Over four days of testimony, Dr. Chaitoff outlined standards that, in his opinion, constituted the relevant standards of medical practice. For instance, Dr. Chaitoff told the jury that a doctor who, “knowing that a patient is intentionally diverting,” nevertheless “is- sue[s] them a prescription for a controlled substance” acts outside “generally acceptable medical practice.” Doc. 388 at 21. The same is true, he opined, for a doctor who “exchange[s] . . . controlled sub- stance for monetary remuneration” or violates rules contained in “the DEA manual 2006” or “Rule 64B8-9.013”—a 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.
Dr. Chaitoff also told the jury that Santos violated these standards. He testified that “100 percent” of Santos’s patient files “fell below the standard of care” and that in “most of them, pre- scriptions for controlled substances . . . were not issued in the course of . . . professional practice.” Doc. 388 at 20. For example, Dr. Chaitoff testified that when Santos first prescribed Chin—the undercover agent—controlled substances, he relied on “an inade- quate history,” and a “physical examination” that was “incom- plete.” Id . at 167. He testified that during Chin and Vasilas’s first joint visit to Santos (the basis for Santos’s conviction on count seven of the second superseding indictment), Santos prescribed con- trolled substances “outside the scope of professional practice” be- cause Santos failed to take a patient “history, [conduct a] complete physical examination,” consider “medical necessity” or “other medications,” or address that the medication failed to improve Va- silas’s reported pain. Id . at 194. Dr. Chaitoff offered similar opinions on later visits Chin and Vasilas made to Santos. See, e.g. , id . at 213 (“Based 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.”) (count nine).
Dr. Chaitoff’s testimony was the heart of the government’s
trial presentation. As the government argued during trial, Dr.
Chaitoff’s testimony was “critical evidence for purposes of [its]
case-in-chief,” and without Dr. Chaitoff, the government would
struggle “[i]n terms of being able to present [its] case.”
Id
. at 86.
Indeed, after the district court struck the bulk of Dr. Chaitoff’s
*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
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
,
Recall that Santos’s three substantive convictions (counts
seven, eight, and nine of the second superseding indictment) were
*34
based on a series of specific visits with a DEA agent, Chin, and a
confidential informant posing as her boyfriend, Vasilas. Yet the jury
acquitted Santos of two counts of substantive violations of
During each of the five visits underlying the indictment, Santos ignored red flags 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 finding 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 Santos’ 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
*35
course of professional practice. If the jury had drawn such an in-
ference, it would have convicted on counts five and six. This seri-
ously undercuts that government’s reliance on the general evi-
dence of the conspiracy—rather than evidence specific to the dis-
crete prescriptions that underlie the
The fourth and final prong of plain error review requires us to consider whether the error “seriously affects the fairness, integ- rity or public reputation of judicial proceedings.” 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 “[t]he risk of unnecessary deprivation of liberty par-
ticularly undermines the fairness, integrity, or public reputation of
judicial proceedings” when the court is responsible for the error.
Rosales-Mireles v. United States
,
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 2376–77 (“[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 evil” (internal quotation marks omitted) (alteration adopted)).
We will not run the risk that the jury transgressed that line. We vacate Santos convictions under § 841—counts seven, eight, and nine of the second superseding indictment.
C. Sufficiency of the Evidence
On remand, the parties again challenge the sufficiency of the
evidence for the conspiracy counts under
A preserved challenge to the sufficiency of the evidence re-
quires us to examine “whether the evidence, when viewed in the
light most favorable to the government, and accepting reasonable
inferences and credibility choices by the fact-finder, would enable
the trier of fact to find the defendant guilty beyond a reasonable
doubt.”
United States v. Monroe
,
The government does not need direct evidence to prove con-
spiracy; circumstantial evidence can prove each element. The first
element, the existence of an agreement, “may be proved by infer-
ences from the conduct of the alleged participants or from circum-
stantial evidence of a scheme.”
Azmat
, 805 F.3d at 1035 (internal
quotation marks omitted). The second element, knowledge of an
agreement, is satisfied if “the circumstances surrounding a person’s
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
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 “red
flags” that would have put a reasonable doctor on notice of the il-
legitimacy of the operation.
See, e.g.
,
Azmat
,
Viewing the evidence in the light most favorable to the gov-
ernment,
see Monroe
,
At the outset, we briefly address the relationship between
Ruan II
and our analysis. As we explained in
Ruan III
, “a conviction
under
1. Duldulao’s Sufficiency Challenge *40 Duldulao argues that there was insufficient evidence to sup- port the elements of the conspiracy charge and, specifically, that the red-flag evidence was weak. We agree with the district court that there was sufficient evidence for the jury to find that he 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 Gonzalez’s testimony that Duldulao agreed to write narcotics prescriptions; staff and patient testimony about Duldulao’s adherence to the plan to write controlled sub- stance prescriptions to most of the clinic’s clientele; staff testimony regarding HPC’s operations while Duldulao served as Medical Di- rector; patient testimony that confirmed the clinic’s standard oper- ating scheme under Duldulao; and Duldulao’s statements to his then-girlfriend Kelly Schleisner about the clinic, including that it was a “pain mill.” Doc. 376 at 6–9. This evidence was sufficient to establish that Duldulao 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 first 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 Gonzalez’s testimony about his interview with Duldulao for the position of Medical Director, HPC staff’s tes- timony about Duldulao’s conduct at the clinic, staff and patient tes- timony about the clinic’s patients, and Duldulao’s statements to *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. Gonzalez’s testi- mony was evidence that Duldulao knew about the suspicious na- ture of HPC from the beginning and nevertheless agreed to get involved. During Duldulao’s job interview, Gonzalez showed him a file that listed the types of controlled substances HPC had previ- ously prescribed for patients. Gonzalez told Duldulao that patient visits were timed and that it was “expected that he would probably take about ten minutes” for each patient. Doc. 382 at 41. To “expe- dite things,” the staff would write out prescriptions before the pa- tient’s visit that Duldulao could sign afterward. Id. at 41–42. This is circumstantial evidence of a scheme to get controlled substances into patients’ hands as quickly as possible without regard to medi- cal need. From this evidence, a jury could find 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 flags
for doctors.
See Iriele
,
Beyond the patients’ appearances, Duldulao heard from
HPC staff that some patients had tested positive for illegal drugs.
Staff also told him that some patients traveled long distances to
reach the clinic, bypassing other pain management doctors and
spending hours in a car despite their supposed chronic pain. Again,
our precedent in
Azmat
warns that these red flags suggest the pa-
tients were seeking drugs without a legitimate medical purpose.
Other circumstances surrounding Duldulao’s presence at
HPC allowed a reasonable jury to attribute knowledge of the con-
spiracy’s unlawful character to him. Duldulao knew that the clinic’s
parking lot was covered with trash, including drug paraphernalia,
and that the clinic had little medical supplies or equipment. He
knew that the staff had no training for or experience with working
*43
in a medical office, 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 “pain mill.” Doc. 386 at 143. The jury therefore could
infer that he had “knowledge of the conspiracy due to his presence
at” the clinic.
See Azmat
,
Second, the element of active participation in the conspiracy
found support in the evidence of Duldulao’s conduct and interac-
tions with the patients. Some HPC patients testified that Duldulao
did not review their medical history forms and that his physical ex-
ams were as brief as two minutes—if they happened at all.
See id.
Duldulao sometimes prescribed combinations of opioids, Xanax,
and Soma, drugs “described in the . . . medical literature as the un-
holy holy trinity for substance abuse.”
Iriele
,
Duldulao argues that this evidence was insufficient to sup- port his conspiracy conviction. He points out that Gonzalez did not testify to telling Duldulao that HPC was a pill mill, that the job was contingent on Duldulao’s agreement to exclusively write prescrip- tions for controlled substances, or that the patients would not have *44 a medical need for these drugs. And, despite his own guilty plea, Gonzalez testified that he “[n]ever” conspired “with Dr. Duldulao to have him write scripts for no legitimate medical purpose.” Doc. 383 at 214. But the jury was free to believe parts of Gonzalez’s 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 officers’ 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 Duldulao’s then-girlfriend Schleisner testified that he told her that he was “pretty sure” some patients were undercover officers. Doc. 386 at 132. Construing the evidence in the govern- ment’s favor, as we must, we conclude that a reasonable jury could have found that these recorded exams were anomalies based on Duldulao’s 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;
*45
inconsistency alone is not a sufficient reason for setting the verdict
aside.
See United States v. Powell
,
And, in any event, the jury’s verdict was not inconsistent.
The
2.
Santos’s Sufficiency Challenge
Turning to Santos, we agree with the district court that there
was sufficient evidence to support the jury’s finding that he know-
ingly joined an agreement to unlawfully dispense controlled sub-
stances. The district court relied on the following types of
*46
evidence: Gonzalez’s testimony, including his admission that
“[t]hat’s what I’m pleading to,” Doc. 383 at 224, when asked on
cross examination whether he conspired with Santos; staff and pa-
tient testimony about Santos’s conduct and interactions with pa-
tients; staff testimony about HPC’s 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 staffers; patient testimony about their experiences, con-
firming that the clinic’s standard operating scheme under Santos
featured “high 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.” Doc. 377 at 8. 8 This evidence
was sufficient to establish that Santos knowingly and voluntarily
8 The district court also relied on another piece of evidence: Santos’s 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 government’s case-in-chief, the district court’s analysis of the
evidence and our review on appeal is limited to the evidence the government
presented.
United States v. Moore
,
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 sufficient evidence to support the jury’s finding that Santos knowingly joined an agree- ment to unlawfully dispense controlled substances. Gonzalez’s tes- timony shows that Santos knew about the suspicious circum- stances at HPC. Santos’s tenure at HPC featured the same red flags that support Duldulao’s conspiracy conviction.
Gonzalez’s 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 “[t]he patients would come in, they wanted their controlled substances.” Doc. 383 at 67. Just like he did with Duldulao, Gonzalez showed Santos a file that contained the types of drugs HPC had prescribed. Santos “was okay with all of it except for he didn’t like the methadone and the Xanaxes together.” Id. Gonzalez notified Santos of the “same for- mat” for timed visits as he had done with Duldulao, and Santos agreed to write prescriptions under those conditions. Id. at 68. San- tos’s job interview presented circumstantial evidence that he knew about the criminal scheme.
Other circumstantial evidence about HPC supported an in- ference that Santos knew about and agreed to the conspiracy. This evidence included many red flags, which we discussed as to Duldulao and which “all stayed the same” under Santos: the office had minimal medical equipment or supplies; the staff was 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 card—not insurance. Doc. 384 at 117–18. Pa- tients showed signs of drug addiction, including slurred speech, “nodding out,” and track marks on their arms. Doc. 383 at 113. Re- gardless, “they got their medications” 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 Santos’s 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 staff 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 “real nerv-
ous” and told Gonzalez “that [they] had to start dropping the med-
ications” 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 suffer a heart attack or a seizure.
*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 Santos’s 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
,
Although we vacate Santos’s
Santos contends that “patient testimony and resort to red
flags cannot mend the evidentiary gap [as to an agreement] be-
cause it does not show any agreement between Dr. Santos and
Gonzalez.” Santos Appellant’s Br. at 54. We disagree. Just as with
Duldulao, the jury was entitled to rely on “inferences 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
D. Dr. Chaitoff’s 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
,
Although Santos failed to raise these objections before the
district court, he argues to us now that Dr. Chaitoff’s testimony
violated the rules of evidence in two ways: first, by opining on San-
tos’s subjective mental state, and second, by reaching a legal con-
clusion. Reviewing Santos’s arguments under the standard of plain
*52
error, we conclude the district court’s decision to admit the testi-
mony was not contrary to binding precedent directly resolving
these legal issues.
United States v. Lejarde–Rada
,
A district court may admit expert testimony that “help[s] the
trier of fact to understand the evidence or to determine a fact in
issue.”
We reject Santos’s first argument—that Dr. Chaitoff’s testi-
mony violated
Santos also fails to show that it was plain error to admit Dr.
Chaitoff’s 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-
tice—the standards of medical care relevant here.
See
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, *54 according to Dr. Chaitoff. He found red flags when he watched vid- eos of undercover officer Chin and confidential informant Vasilas visiting Santos’s 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 Santos’s 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 pair’s two other visits.
Although we vacate Santos’s convictions under
Ruan II
does not undermine that conclusion. As Santos con-
cedes,
Ruan II
“left the door ajar about how to prove mens rea.”
Supp. Br. of Appellant Santos at 13. But a finding of plain error must
be justified by on-point authority.
Lejarde–Rada
,
E. Santos’s Motion to Strike Dr. Chaitoff’s 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 Duldulao’s and Santos’s 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 Duldulao’s activities at a second pain clinic and alleged pill mill that the district court excluded from evidence after granting a motion in limine. Dr. Chaitoff’s 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. Chaitoff’s testimony. The district court granted Duldulao’s motion in part, striking Dr. Chaitoff’s testi- mony regarding Duldulao’s 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. Chaitoff’s testimony about him, too. We disagree. Alt-
hough the court deemed Dr. Chaitoff a “less than reliable witness”
because of his memory problems and lack of candor, it was within
the court’s discretion to deny Santos’s motion to strike. Doc. 388
at 97. Only one topic was off-limits in Santos’s cross-examination:
*57
the evidence about Duldulao’s other pain clinic that the court’s in
limine order excluded. That limit did not substantially affect San-
tos’s 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. Chaitoff’s other shortcomings through thorough
cross-examination.
See United States v. Williams
,
F. Santos’s Sentence
Santos previously challenged his sentence, and we affirmed.
On remand, we need not reconsider the merits of his arguments in
light of
Ruan II
. Because we vacate Santos’s convictions on counts
seven, eight, and nine, we vacate his sentence, too.
See United States
v. Fowler
,
IV. CONCLUSION For the above reasons, we AFFIRM Duldulao’s conviction on count one of the second superseding indictment. We AFFIRM Santos’s conviction on count one, VACATE Santos’s convictions on counts seven, eight, and nine, VACATE Santos’s sentence, REMAND for resentencing, and REMAND for a new trial on counts seven, eight, and nine.