For years, accused drug dealer Tiffany Masunaga was forced to keep a secret about former Honolulu deputy prosecutor Katherine Kealoha.

If she blabbed, and Kealoha found out, it meant the possibility of decades behind bars.

Masunaga wants that threat to go away, now that Kealoha is in the Federal Detention Center.

Masunaga’s attorney, William Harrison, filed a request to dismiss the criminal case against Masunaga in state circuit court on Oct. 31. He said his client was the victim of prosecutorial misconduct, some of the worst he’s seen in nearly 40 years of practicing law.

Tiffany Masunaga.

Tiffany Masunaga has been struggling for years to get out from under drug charges filed against her in a case that has grabbed the attention of federal prosecutors.

Cory Lum/Civil Beat

Masunaga was arrested at her home in 2015 along with Alan Ahn, a Honolulu police officer. The police seized all sorts of drugs in the house, including cocaine, marijuana and a number of prescription painkillers. They also found the deadly opioid fentanyl.

Together, Masunaga and Ahn were charged with a series of felonies.

Now, years later, Kealoha has admitted in court to taking control of the investigation and subsequent prosecution to cover for her younger brother, Rudolph Puana, the man who federal investigators say supplied the prescription drugs.

Masunaga’s attorney, William Harrison, says that should be enough to clear his client.

“This is clearly the worst kind of conflict that a prosecutor could be in,” Harrison said. “That being said I have attempted on previous occasions to get the prosecutor’s office disqualified and they fought me tooth and nail on that even though I’m sure they had to know what was going on.”

The request comes after Kealoha and her husband, former Honolulu police chief Louis Kealoha, were found guilty in June of federal conspiracy and related charges for attempting to frame a family member after a dispute over money.

The couple subsequently pleaded guilty to other charges, including those related to bank fraud, identity theft and drugs.

Katherine Kealoha leaves District Court after guilty verdict.

Katherine Kealoha awaits sentencing after being found guilty of a series of crimes, including conspiracy.

Cory Lum/Civil Beat

Katherine Kealoha in particular accepted a plea deal on Oct. 22 related to her actions in the Masunaga drug case, admitting that she used her position as a prosecutor to steer the narcotics investigation away from her and her brother.

Still, the state charges against Masunaga linger as the Hawaii Attorney General’s office, which has since taken control of the case considers how to respond.

“She did this to protect her brother,” Harrison said of Kealoha.

“She told my client not to worry and that she had her back, when really she did not. That’s the most egregious form of prosecutorial misconduct, I think, when the prosecutor basically lulls you into believing they’re helping you when in fact they’re harming you.”

Kealoha and her younger brother, Rudolph Puana, were accused earlier this year by the U.S. Justice Department of running a prescription drug ring.

Puana is a double-board certified anesthesiologist who owned pain clinics in Hawaii and included his sister, Kealoha, among his patients.

Louis Kealoha waves to media as he leaves hearing on July 11. 2019

Former Honolulu police chief Louis Kealoha is a central character in one of the largest public corruption scandals to play out in state history.

Cory Lum/Civil Beat

According to federal prosecutors, Puana, Kealoha and their friends, including local author Christopher McKinney, would trade prescription drugs, such as fentanyl and oxycodone, for cocaine. Authorities say Kealoha was using cocaine even while working as a city prosecutor.

In July 2015, a Honolulu police detective working for the department’s secretive Criminal Intelligence Unit learned that Puana and McKinney were involved in the alleged drug scheme.

That detective, Daniel Sellers, grew up with Puana and McKinney. He also knew Kealoha. She was his former high school girlfriend and the wife of his boss at the time, Honolulu Police Chief Louis Kealoha.

Federal officials say Sellers told Kealoha that Puana and McKinney were buying cocaine from Masunaga and that another Honolulu police officer, Alan Ahn, appeared to be involved in the illicit activity.

According to the plea agreement, that’s when Kealoha had herself assigned to the case and manipulated the investigation away from her brother and her friend, McKinney.

Kealoha admitted in her plea agreement that she offered Masunaga and Ahn favorable plea deals to conceal her brother’s involvement in the case.

She also tried to cultivate a friendly relationship with Masunaga while at the same time prosecuting her for a series of felonies. Kealoha, however, tried to keep this contact secret by communicating with Masunaga through encrypted messaging applications.

Deputy Prosecutor Duane Kokesch, center Attorney William Harrison and right, Deputy Atty Jan Futa walk to Judge Trader's court room for Grube's hearing.

William Harrison, center, is flanked by deputy prosecuting attorneys Duane Kokesch and Jan Futa after a hearing to unseal records in Tiffany Masunaga’s criminal case.

Cory Lum/Civil Beat

Harrison pointed out that these weren’t the only problems with the case. The concerning conduct went well beyond Kealoha, he said.

Masunaga’s defense lawyer at the time was Myles Breiner, a high profile Honolulu attorney who has a history of filing lawsuits against the police. Breiner, however, was also working for Kealoha while she was prosecuting his client Masunaga, something that Harrison described as an egregious conflict of interest.

Breiner was Masunaga’s attorney when she entered into a cooperation agreement with the Honolulu Prosecuting Attorney’s Office that effectively prevented her from speaking to federal authorities or anyone else outside of the city agency about what she knew about the case.

Instead, Harrison said she was used by prosecutors who were conducting a secret grand jury that federal officials say was part of a “fabricated investigation” to help cover for a speeding ticket Kealoha dismissed for a business acquaintance.

Among the prosecutors involved in those grand jury proceedings with Masunaga, Harrison said, were Honolulu Prosecuting Attorney Keith Kaneshiro and several of his top deputies, including Armina Ching, Jan Futa and Chasid Sapolu.

Kaneshiro has since been named the target of the Justice Department’s ongoing criminal investigation while Sapolu has been notified he is a subject of the probe.

Prosecutor Keith Kaneshiro announces a 3rd possible trial for Christopher Deedy.

Honolulu Prosecuting Attorney Keith Kaneshiro is on leave with pay while being investigated by the U.S. Justice Department for alleged criminal activity.

Cory Lum/Civil Beat

The prosecutors continued to bend justice to their will, Harrison said, when they convinced a former state court judge to seal any record of their cooperation agreement with Masunaga from public view.

The Hawaii Supreme Court eventually overturned that decision after a legal challenge from a Civil Beat reporter.

Both Futa and Sapolu had argued against the release of the records.

Harrison said the cooperation agreement the prosecutors attempted to keep hidden is what effectively prevented his client from speaking to federal authorities while they were investigating the Kealohas and others in HPD and the Honolulu Prosecuting Attorney’s Office.

That changed, he said, when Hawaii Attorney General Clare Connors petitioned the Supreme Court to suspend Kaneshiro and took over the case due to conflicts of interest.

Harrison said that if Masunaga violated the city prosecutors’ cooperation agreement by talking to an outside investigative agency, any leniency in her case could be revoked and she could face a minimum of 20 years in prison based on the charges still looming overhead.

“There was a big carrot there for her to keep quiet,” he said. “But it really wasn’t to her benefit to do that.”

The Hawaii Attorney General’s Office has yet to respond to Harrison’s motion.

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