The criminal trial for the brother of disgraced former Honolulu Deputy Prosecutor Katherine Kealoha, Rudolph Puana, a Big Island anesthesiologist accused of running an illicit prescription drug ring, is set to start this week following repeated delays due to the Covid-19 pandemic.

The trial is scheduled to begin in the U.S. District Court of Hawaii on Tuesday and could last up to two weeks. Jurors are expected to hear from dozens of witnesses including Kealoha, who is currently serving a 13-year sentence at a federal prison in California on corruption charges involving Puana and Kealoha’s ex-Honolulu police chief husband, Louis Kealoha.

Puana was indicted in September 2019 on charges that include health care fraud, unlawful possession of a firearm and conspiracy to distribute oxycodone and fentanyl.

Rudolph Puana
Rudoph Puana is accused of running a prescription drug ring by writing prescriptions for thousands of painkillers for his friends. Hawaii News Now

Federal prosecutors say Puana abused his privileges as a licensed physician by writing medically unnecessary opioid prescriptions for several close friends, who then sold the pills for a profit or traded them for cocaine, to which Puana admitted he was addicted.

Those friends include Christopher McKinney, a well-known local novelist, who obtained more than 3,200 oxycodone pills between April 2015 and October 2017 using Puana’s prescriptions, according to court records.

The pair allegedly found a small pharmacy near McKinney’s home willing to fill the prescriptions. McKinney sold the pills for $15 apiece and bought cocaine, which he would use with Puana, prosecutors said.

“Is it just me or are you smelling celebration when I come in December,” Puana wrote to McKinney in a text message included in a trial brief filed earlier this month.

“Oh, Im (sic) smelling it. Like 3.5 grams of celebration,” McKinney wrote back, according to the court document.

For others, the pills Puana prescribed served as an additional source of income, prosecutors said.

This included Pauna’s close friends, Josh DeRego and his wife Elena Rodriguez, who allegedly used the money made from selling oxycodone to pay their children’s private school tuition.

“One month after the oxycodone prescriptions started flowing, DeRego and Rodriguez made their first payment to their children’s private school in about six months,” prosecutors wrote in a motion filed last July.

Prosecutors said DeRego and Puana were “almost brotherly” and would golf, drink and do cocaine together. Puana allegedly wrote prescriptions for over 5,000 oxycodone pills to DeRego and his wife between February 2013 and January 2016, and connected them with a Big Island drug dealer identified by prosecutors only as “the Hawaiian.”

DeRego, Rodrigues and McKinney — who were not charged in connection to the case — are all listed as witnesses the prosecution intends to call against Puana.

Katherine Kealoha also participated in her brother’s drug distribution scheme and admitted doing so in a plea agreement she accepted in October 2019, after being named as a co-defendant in the case.

The former prosecutor said her brother would write her “medically unnecessary” prescriptions that she would sell or barter for cocaine, according to prosecutors.

Retired HPD Chief Louis Kealoha Katherine Kealoha leave District Court.
Former Honolulu Deputy Prosecutor Katherine Kealoha is set to be a witness in the drug trial against her brother, Rudolph Puana. Cory Lum/Civil Beat

When Puana was under investigation by the Honolulu Police Department, Kealoha assumed control of the case in an attempt to shield her brother from prosecution, according to court records.

In a separate case, Kealoha pleaded guilty to framing a family member to end a financial dispute.

Kealoha’s expected testimony about her brother has been a point of contention in the lead-up to the trial.

“The government has announced its intent to call Katherine Kealoha as a witness in this case and, one assumes, to ask the jury to credit her testimony,” Puana’s lawyer, Clinton Broden, wrote in a court filing. “This is despite the fact that the government has previously been vociferous in proclaiming that Kealoha was a ‘walking crime spree.’”

Broden wrote that the prosecution is speaking “out of both sides of its mouth” by calling Kealoha as a witness after federal prosecutors branded her a liar and master manipulator in her separate criminal conspiracy case.

“The fact that the government, in an effort to win at any costs, would call a witness who it believes ‘obstruct(s) and interfere(s) with the search for the truth’ and has aided and abetted perjury, makes a mockery of our criminal justice system which would cause any reasonable person to recoil in shock,” Broden wrote.

On Thursday, Assistant U.S. Attorney Colin McDonald responded to Broden’s complaint, calling it an attack on the prosecution, not Kealoha’s truthfulness.

“His desire to … ‘impeach’ Katherine by using the prosecutor’s own words makes clear his true intent: to impeach and impugn the prosecution by suggesting the prosecution is being duplicitous about Kealoha’s credibility,” McDonald wrote.

Judge J. Michael Seabright has not yet ruled on Broden’s motion to admit statements U.S. attorneys have previously made about Kealoha.

Kealoha’s testimony was not the first point of contention in the case against Puana.

In October, Broden filed a motion to prohibit references to terms such as the “opioid epidemic” or “opioid crisis,” saying that their use could sway a jury.

“References to the public controversy surrounding opioid use would serve no purpose other than to imply to the jury that Dr. Puana is ‘guilty-by-association’ or that convicting Dr. Puana would address a social problem,” Boden wrote.

Seabright granted the request to exclude discussion of the “opioid crisis” or related terms from the trial.

In a filing earlier this month, prosecutors outlined their plan to use Puana’s text messages and phone calls, alongside co-conspirator testimony and data on prescriptions Puana wrote, to assert his guilt. They also plan to include a notebook Puana kept to track his allegedly illicit prescriptions, according to court documents.

Meanwhile, Puana’s defense team plans to argue that his prescriptions were legitimate.

“Dr. Puana … strongly maintains that the medications prescribed to the individuals were for legitimate medical purposes and will present significant evidence supporting this position,” Broden wrote in a trial brief.

“For example, Dr. Puana prescribed opioids to Chris McKinney for well established chronic back pain; he prescribed opioids to Joshua DeRego for shoulder pain that eventually required two operations; and he prescribed opioids to Elena Rodriguez (DeRego’s wife) for chronic regional pain syndrome related to her knee which led a surgeon to recommend surgery.”

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