USCA11 Case: 20-13973    Document: 96-1      Date Filed: 11/29/2023   Page: 1 of 57




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

                           ____________________

                                 No. 20-13973
                           ____________________

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


                                                  Defendants-Appellants.


                           ____________________

                  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 “pill mill,” the Supreme
        Court vacated our judgment and remanded for further considera-
        tion in light of Ruan v. United States, 

 (“Ruan
        II”). See United States v. Duldulao, No. 20-13973, 

        (11th Cir. Dec. 21, 2021) (unpublished), vacated sub nom. Santos v.
        United States, 

. 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, 

, 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
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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 

. 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 

.
               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