[PUBLISH] In the United States Court of Appeals For the Eleventh Circuit

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No. 20-13973 ____________________

UNITED STATES OF AMERICA, Plaintiff-Appellee, versus KENDRICK EUGENE DULDULAO, MEDARDO QUEG SANTOS,

Defendants-Appellants.

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Appeal from the United States District Court for the Middle District of Florida D.C. Docket No. 8:17-cr-00420-MSS-AEP-4 ____________________ USCA11 Case: 20-13973 Document: 96-1 Date Filed: 11/29/2023 Page: 2 of 57

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 “pill mill,” the Supreme Court vacated our judgment and remanded for further considera- tion in light of Ruan v. United States, 142 S. Ct. 2370 (2022) (“Ruan II”). See United States v. Duldulao, No. 20-13973, 2021 WL 6071511 (11th Cir. Dec. 21, 2021) (unpublished), vacated sub nom.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 Court’s 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 “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, 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 (“HPC”). 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 USCA11 Case: 20-13973 Document: 96-1 Date Filed: 11/29/2023 Page: 3 of 57

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. § 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. § 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 “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. 38