United States v. Duldulao

87 F.4th 1239

UNITED STATES of America, Plaintiff-Appellee, v. Kendrick Eugene DULDULAO, Medardo Queg Santos, Defendants-Appellants.

No. 20-13973

United States Court of Appeals, Eleventh Circuit

Filed: November 29, 2023

Appeal from the United States District Court for the Middle District of Florida, D.C. Docket No. 8:17-cr-00420-MSS-AEP-4

Holly Lynn Gershow, Gregory D. Pizzo, DOJ-USAO, Appellate Division, Tampa, FL, U.S. Attorney Service — Middle District of Florida, U.S. Attorney, DOJ-USAO, Appellate Division, Tampa, FL, for Plaintiff-Appellee.

Thomas A. Burns, Burns, PA, Tampa, FL, for Defendant-Appellant Medardo Queg Santos.

David T. Weisbrod, David T. Weisbrod, Esq., Tampa, FL, Jeffrey G. Brown, Brown Doherty Little, Saint Petersburg, FL, for Defendant-Appellant Kendrick Eugene Duldulao.

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 consideration in light of Ruan v. United States, 597 U.S. 450, 142 S. Ct. 2370, 213 L.Ed.2d 706 (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 See United States v. Duldulao, No. 20-13973, 2021 WL 6071511 (11th Cir. Dec. 21, 2021) (unpublished), vacated sub nom.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, — U.S. —, 143 S. Ct. 350, 214 L.Ed.2d 167 (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 doctors, 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 management clinic in Tampa, Florida called Health and Pain Clinic ("HPC"). HPC liberally dispensed controlled substances to its patients, who paid with cash or credit, exhibited obvious signs of drug addiction, and received little attention from doctors. A jury 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 practice, 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 substances 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 substances that Duldulao would use to treat the clinic's patients. Doc. 382 at 36. Gonzalez also told Duldulao and Santos about key aspects of the business model: very short, timed patient appointments; high patient volume (30-40 patients per day); and up-front payment only—HPC did not accept insurance.

Other characteristics suggested that the clinic was not a legitimate medical operation. The clinic had barely any medical equipment—only an exam table for the patients to sit on—or supplies. HPC staff who ran the front desk and did patient intake had no medical or administrative training. Yet they wrote prescriptions for controlled substances for the doctor to sign after each patient'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 patients 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 wrappers, 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 sometimes 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 patients 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 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 examinations. Sometimes he spent up to five minutes on the physical exam; sometimes he simply did not perform one. He spent little time on patient medical history. When he went on vacation, his patients picked up prewritten, postdated prescriptions without any medical exam at all. He wrote prescriptions for controlled substances for patients even when they bore visible track marks or had traveled from long distances—both red flags for controlled substance abuse, according to the government's medical expert witness, Dr. Kevin Chaitoff. Duldulao prescribed controlled substances in dangerous combinations, allowing his patients to mix Xanax, methadone, and a muscle relaxer called Soma. He even admitted to his girlfriend that he worked at a "pain mill." Doc. 386 at 143.

When Santos replaced Duldulao as HPC's Medical 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 prescribed drugs in the same dangerous combinations that Duldulao 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 "prohibition" 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 Santos discussed no alternative forms of treatment, Santos wrote Chin a prescription for hydrocodone, which Santos changed to a prescription for oxycodone a few days later. Chin told Santos that she would fill the prescriptions in Alabama.

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 experienced 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 required 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 substances. Id. at 0:42-0:44 ("In Alabama I'm gettin' em."). And Chin revealed that she lived in Panama City, meaning she travelled almost 400 miles to HPC's Tampa location. Nevertheless, Santos wrote Chin a prescription that increased the total amount of controlled substances she received and gave her access to higher-dose pills.

At Chin's next visit, Vasilas came with her. Vasilas, a returning 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...