United States v. Duldulao, Case No. 20-13973 (11th Circuit Court of Appeals, filed December 21, 2021) Court allows expert witness with reliability and “candor” issues to testify to ultimate issue in dispute; sufficiency of the evidence challenges denied.

Reading this case, it’s not too difficult to see how the government obtained its conviction since the evidence appears fairly damning.  Still, it’s problematic when the courts allow an expert to testify to an ultimate issue in a case (the defendants’ subjective thoughts) and when that expert has reliability and candor issues.  Here’s what happened:  Kendrick Eugene Duldulao (“Duldulao”) and Medardo Queg Santos (“Santos”) served as Medical Directors of a pain management clinic in Tampa called “Health and Pain Clinic” (“HPC”). At the conclusion of trial, a jury in the United States District Court for the Middle District of Florida convicted Duldulao of one count of conspiracy to distribute and dispense controlled substances under 21 U.S.C. § 846. The jury also convicted Santos of conspiracy under § 846 as well as three substantive counts of dispensing and distributing controlled substances under 21 U.S.C. § 841. The district court sentenced Duldulao to twelve months and one day of imprisonment and Santos to six years of imprisonment.


Duldulao and Santos appealed their convictions to the Eleventh Circuit Court of Appeals. Duldulao and Santos argued there was insufficient evidence they knowingly agreed to participate in a pill mill conspiracy. Santos further challenged his conviction on the grounds that the district court made two reversible trial errors: (1) admitting testimony from the government’s expert witness in pain management, Dr. Chaitoff, about his treatment of patients and (2) denying Santos’ motion to strike Dr. Chaitoff’s testimony. Santos also appealed his sentence, arguing that the district court should have applied a clear-and-convincing standard, rather than a preponderance-of-the-evidence standard, to any relevant conduct findings that would increase his offense level.


Duldulao’s Sufficiency Challenge


First, Duldulao argued that there was insufficient evidence to support the elements of the conspiracy charge and, specifically, that there was weak circumstantial evidence of “red flags” that would have put a reasonable doctor on notice of the illegitimacy of the operation. See, e.g., United States v. Azmat, 805 F.3d 1018, 1036 (11th Cir. 2015). The court disagreed and found the jury reasonably could have inferred Duldulao had knowledge of the criminal object of the conspiracy.


First, the court found that testimony from the owner of HPC was evidence that Duldulao knew about the suspicious nature of HPC from the beginning and nevertheless agreed to get involved. This included HPC’s owner’s testimony that he showed Duldulao a file during his interview that listed the types of controlled substances HPC had previously prescribed patients and telling Duldulao that patients visits were timed and it was “expected that he would probably take about ten minutes” for each patient. HPC’s owner also testified that he told Duldulao that, to “expedite things,” the staff would write out prescriptions before the patient’s visit that Duldulao could sign afterward.


In addition, the court noted that witnesses described HPC patients as looking like drug abusers—for example, they were “a little too sleepy,” slurred their speed, had bloodshot eyes or dilated pupils, had visible track marks, smelled of marijuana, and “nod[ed] out” in the waiting room—and these signs would have been a red flag to a reasonable doctor. Further red flags include that Duldulao heard from HPC staff that some patients had tested positive for illegal drugs and 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. The court also noted that Duldulao knew the clinic’s parking lot was covered with drug paraphernalia, the clinic itself had little medical supplies or equipment, the clinic’s staff had no training or experience with working in a medical office, and HPC did not accept insurance—only cash was accepted.


With respect to Duldulao’s active participation in the conspiracy, the court noted that HPC patients testified that Duldulao did not review their medical history forms, his physical exams were as brief as two minutes (if they happened at all), he sometimes prescribed combinations of controlled substances considered the “unholy holy trinity for substance abuse,” and he signed prewritten and postdated prescriptions and left them with HPC staff when he was on vacation so that patients could pick them up without an exam or a physician present.


The court noted that the jury did hear countervailing evidence, including video footage from undercover officers’ appointments with Duldulao showing that he performed a thorough physical exam, asked about their medical history, asked about their current medications, and advised them not to mix opiates with alcohol. However, Duldulao’s girlfriend also testified that he was “pretty sure” some of his patients were undercover officers. The court concluded that a reasonable jury could have found that these recorded exams were anomalies based on Duldulao’s suspicions that he was dealing with undercover officers.


Santos’ Sufficiency Challenge


The court also found that there was sufficient evidence to support Santos’ convictions. Regarding Santos’ knowing agreement to write illegal prescriptions, the court relied on the same testimony from HPC’s owner that he made it clear to Santos that patients “wanted their controlled substances,” that he showed Santos a file that contained the types of drugs HPC had prescribed, and that he notified Santos of the “same format” for timed visits as he had done with Duldulao, and Santos agreed to write prescriptions under those conditions. Santos also had knowledge of the same red flags discussed above, including that the office had minimal office equipment, the staff were untrained, patients traveled long distances to the clinic, the parking lot was littered with syringes, and HPC only accepted cash. He also knew that patients showed signed of drug addiction.


Regarding Santos’ active participation in the conspiracy, he not only postdated prewritten prescriptions when he was on vacation, but he also was convicted of substantive offenses under § 841 based on his interactions with purported patients who were actually government agents. In these visits, these purported patients admitted to diverting their medication (a serious red flag that suggest drug abuse); yet, Santos still provided the increased quantities requested.


The court held that based on HPC’s owner’s testimony, the multiple red flags, and Santos’ conduct together, a reasonably jury could have found that Santos agreed to work at a pill mill and unlawfully distribute controlled substances.




Santos’ Challenge to Government Expert Testimony


Santos argued that Dr. Chaitoff’s testimony violated the rules of evidence in two ways: (1) by opining on Santos’ subjective mental state in violation of Rule of Evidence 704(b) and (2) by reaching a legal conclusion. The court, however, found no plain error.


First, the court held that Dr. Chaitoff testified only about Santos’ conduct and his professional opinion of that conduct, but he did not speculate about what was going on in Santos’ mind.


Second, the court held that there was no plain error in admitting Dr. Chaitoff’s testimony despite the fact that his testimony reached the ultimate issue of whether Santos prescribed drugs for no legitimate medical purpose and outside the usual course of professional practice—the standard of medical care that governs the case. The court summarized Dr. Chaitoff’s testimony as including background testimony about these standards; testimony that their meanings are derived from the DEA manual, state and federal regulations, and his pain management practice; testimony describing the process he follows before prescribing controlled substances by giving examples from his experience; and testimony regarding red flags that would warn him that patients might be abusing their medication (including red flags noted in videos from undercover officers).


Dr. Chaitoff gave his opinion about an ultimate issue when he testified that, at three visits, Santos prescribed the purported patients controlled substances for no legitimate medical purpose and outside the scope of professional practice. The court held that Dr. Chaitoff’s testimony did not violate Rule 704(b) because, under Azmat, medical experts are permitted to testify about the ultimate issue of the appropriate standard of care.


Santos’ Challenge to the Denial of his Motion to Strike Expert Testimony


The court denied Santos’ challenge to the district court’s denial of his motion to strike Dr. Chaitoff’s testimony. Even though the district court deemed Dr. Chaitoff a “less than reliable witness” because of his memory problems and lack of candor, the court held that it was within the district court’s discretion to deny Santos’ motion to strike. The court also held that Santos was not prejudiced because he still had an opportunity to effectively cross-examine Dr. Chaitoff and impeach his credibility.

In other words, so long as defense counsel has an opportunity to challenge a witness, the court is going to allow that witness– no matter how problematic– to testify at trial.