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Tiffany Masunaga was more than eight months pregnant on Aug. 13, 2015, when Honolulu police officers armed with assault rifles burst through her front door as part of a 6 a.m. drug raid.

They moved quickly through the home, seizing all manner of narcotics — cocaine, marijuana and several prescription medications, including hydrocodone, alprazolam and 114 transdermal patches of the high-powered opioid fentanyl.

Masunaga was arrested along with Alan Ahn, a Honolulu police officer who was with her at the time.

They were indicted and charged with a series of felonies that threatened to put them away for years.

But now — nearly four years later — the case is a linchpin in a growing federal investigation into public corruption and abuse of power in Hawaii law enforcement.

So far, Honolulu’s former police chief Louis Kealoha and his wife, Katherine Kealoha, who used to work as a city prosecutor, have been indicted for attempting to frame a family member with the help of several officers who were part of a special police force.

At least five officers have been charged with criminal activity — two of whom have already pleaded guilty — as federal investigators continue to peel away layers of alleged wrongdoing.

Honolulu Prosecuting Attorney Keith Kaneshiro, who has taken a paid leave of absence, is now a target of the U.S. Justice Department’s ongoing criminal investigation, as is Mayor Kirk Caldwell’s top civil lawyer, Donna Leong, who helped craft a $250,000 payout for Louis Kealoha.

Masunaga’s case highlights just some of the latest allegations in what has become the largest public corruption scandal in Aloha State history.

A Feb. 7 indictment says that some of the prescription drugs found in Masunaga’s home belonged to Katherine Kealoha’s younger brother, Rudolph Puana, a double-board certified anesthesiologist from the Big Island who owned and operated a pain clinic.

According to investigators, the siblings were running an illicit prescription drug ring from 2012 to 2018 with a handful of their friends so that they could earn extra income and feed Puana’s cocaine habit. 

Kealoha is also alleged to have used cocaine recreationally even while working as a prosecutor.

In 2015, when Kealoha learned Honolulu police were investigating Masunaga — something that threatened to expose their criminal enterprise — she used her position as a city prosecutor to steer the investigation away from her brother, authorities say.

But while the indictment focuses on Kealoha’s manipulation of the criminal justice system, it’s clear she couldn’t have done it alone.

Documents and records obtained by Civil Beat suggest the obfuscation went beyond Kealoha, permeating nearly every aspect of Masunaga’s case, from the planning of the police raid to a cooperation agreement city prosecutors fought to keep secret.

A trusted police officer tipped her off to the investigation and her own defense lawyer played a role in helping her get closer to Masunaga.

Keith Kaneshiro proved to be a loyal boss, one who was willing to defend her in public.

And it was Kaneshiro who signed a cooperation agreement between his office and Masunaga that effectively barred Masunaga from talking to anyone — including outside investigators — about Kealoha and Puana’s alleged criminal dealings.

“This case is really messed up,” said William Harrison, a Honolulu defense lawyer who now represents Masunaga. “From the beginning, everything I read in the files and everything I learned struck me as odd. And after discussing the facts with my client I was incredulous.”

Kealoha’s attorney, Cynthia Kagiwada, did not respond to a request for comment for this story.

An Ex-Boyfriend Lends A Hand

In July 2015, the Feb. 7 indictment says, an HPD detective told Katherine Kealoha that her younger brother, Rudolph Puana, was buying cocaine from Masunaga.

That detective was Daniel Sellers, a member of the Honolulu Police Department’s elite Criminal Intelligence Unit.

The CIU, as it’s often called, was made up of officers hand-picked by Honolulu’s then-police chief, Louis Kealoha.

Their mission was to work in secret, gathering intelligence on everything from terrorist plots to organized crime. They could conduct surveillance and pass along what they learned, but they were instructed never to write reports. They were supposed to work in the shadows.

But the connections between Sellers and Katherine Kealoha went deeper than the HPD.

Sellers was her boyfriend in high school. They both attended the Mid-Pacific Institute in Manoa, where Sellers was an all-star baseball player.

When Sellers learned Puana and his friend, Chris McKinney, were purportedly buying cocaine from Masunaga and Ahn, he reached out to Kealoha, who at the time was a deputy prosecutor and led the career criminal division.

Kealoha and her brother had grown up with McKinney in Kahaluu on Oahu’s Windward Side. They were close friends linked by proximity and a rough-and-tumble upbringing. McKinney, a well-known local author, even co-wrote a book with Puana that published in 2014.

“I think the target here all along has been Katherine, and Rudy is sort of a dolphin caught up in a tuna net.” — Clint Broden, attorney for Rudolph Puana

According to court records, Sellers and Kealoha called a meeting at Puana’s apartment to discuss the drugs.

They told Puana and McKinney that they were investigating Masunaga and Ahn, and they wanted to get more information.

Shortly after the meeting, the records say, Puana and McKinney left the country. While they were gone they learned of Masunaga and Ahn’s arrests.

Clint Broden, a Texas lawyer who represents Puana, said his client had no relationship with Masunaga, and said that his client appears to be the bycatch of a larger investigation into his sister.

“We certainly are going to vigorously contest the charges,” Broden said. “I think the target here all along has been Katherine, and Rudy is sort of a dolphin caught up in a tuna net.”

Richard Sing, an attorney for Sellers, declined to comment.

McKinney did not respond to a Civil Beat request for an interview, nor did his attorney.

Kealoha’s Name Missing From Reports

To protect her brother, federal prosecutors say, Katherine Kealoha needed to break the law.

According to the indictment, once she learned her brother might be on the wrong end of an HPD criminal inquiry she arranged to have herself assigned to the case.

Kealoha, even though she was a prosecutor, became a key part of the investigation into Masunaga and Ahn.

The latest indictment says she wrote the search warrant that was used to justify the early morning drug raid. And while she knew her brother was a source of some of the drugs, she withheld that information from HPD investigators.

She also blocked police detectives from interviewing Masunaga or Ahn about the drugs and where they came from.

Honolulu police reports, however, told an incomplete story, one that practically omitted Kealoha from the picture.

On Aug. 14, 2015, the day after the drug raid, Det. Kyle Numasaki and Cpl. Grant Jhun of the narcotics division each wrote reports discussing the origins of the case.

Numasaki wrote that confidential informants had told law enforcement that Masunaga was selling cocaine and prescription pills out of her house and that Ahn would provide protection.

Jhun said the information came to him via the Criminal Intelligence Unit, which he said was conducting an internal investigation into “police corruption.”

There was no mention of Puana or McKinney’s involvement in the alleged drug scheme.

“Obviously, it was not coming from some street person who robbed a pharmacy because that would be easy to track.” — William Harrison

Numasaki and Jhun said they spent several days doing surveillance on Masunaga and Ahn with members of CIU, although they didn’t provide names of the officers they worked with.

Their assignment included following Ahn as he drove a 2005 Maserati around the city.

“During mobile surveillance of the Maserati, Corporal Jhan and I observed Ahn frequently pull over to the sidewalk, stop, and visually assess his surrounding before moving on,” Numasaki wrote.

“Ahn would also drive very slow below the speed limit and then suddenly speed up and then slow down again. Based on my training and experience in surveillance technique, Ahn was utilizing counter surveillance to avoid being followed.”

On the evening of Aug. 12, the officers said they saw a man — whose name was redacted from the police reports — drive to Masunaga’s house in a gray Nissan pickup truck.

They said Masunaga got in his truck and gave him a brown paper bag.

Numasaki and Jhun followed the vehicle to a Times Supermarket on Beretania Street.

Numasaki said that when they approached the vehicle, the driver let out an audible sigh and put his head on the steering wheel. He then reached into the back and turned over the paper bag.

The officers found two ounces of cocaine inside that the man said he purchased for $3,400.

He also gave them a separate black bag with ecstasy, marijuana and hydrocodone.

What they left out of their reports — at least initially — was that Katherine Kealoha and Daniel Sellers showed up at the Times parking lot to talk with the driver.

It wasn’t until November 2017 — more than two years later — that Jhun’s supervisors made him write a follow-up report that included both Kealoha and Sellers’ names.

He said they had met with the driver “confidentially,” and that Kealoha had offered him immunity in exchange for his testimony against Masunaga.

Harrison, Masunaga’s attorney, says he has never received Jhun’s 2017 report despite the fact that the case is still ongoing. Civil Beat obtained the report through a public records request, but Harrison said he should have received a copy as well.

He also said that in all the HPD files he received, not once did he see mention of Kealoha’s involvement.

“I didn’t get that at all,” Harrison said.

Also missing from the reports, he said, was any reference to officers inquiring where the fentanyl had come from.

“That would be one of the primary areas of investigation because fentanyl is so dangerous and controlled,” Harrison said. “Obviously, it was not coming from some street person who robbed a pharmacy because that would be easy to track. Clearly it was coming through a pharmacy or a doctor.”

The timing of Jhun’s follow-up report is noteworthy, too.

It was written one month after Katherine and Louis Kealoha were indicted on federal charges for conspiracy, obstruction of justice and bank fraud, and a new police chief, Susan Ballard, was installed.

Four other police officers were indicted at the same time, including Sellers and three other members of the CIU — Derek Hahn, Gordon Shiraishi and Minh-Hung “Bobby” Nguyen.

The Masunaga reports highlight another curious detail about the drug raid, that although there were three people in the house only two — Masunaga and Ahn — were arrested.

A third person in the home, Meagan Fujimoto, was not apprehended or charged. Fujimoto had a family relationship to Nguyen, who had previously been married to Kealoha’s niece.

Michelle Yu, a spokeswoman for HPD, said the department and its chief, Ballard, did not want to comment on the case or the police reports that were provided to Civil Beat as part of a state public records request.

‘Can’t Wait For This Shit To Be Over’

Once the case moved to the Honolulu Prosecuting Attorney’s Office and Kealoha was successful in indicting Masunaga and Ahn, Masunaga hired local attorney Myles Breiner to defend her in the criminal case.

At the time, Breiner had a reputation as a hard-nosed defense lawyer who wasn’t afraid to take on HPD or the prosecuting attorney’s office. He’d filed several lawsuits against the police department for officer misconduct and excessive use of force.

Breiner also publicly accused Kealoha of prosecutorial misconduct for her mishandling of a gambling case in which he represented one of the defendants.

But in May 2016 — in the midst of defending Masunaga — he took on Kealoha and her husband as clients to help shield them from federal investigators.

That meant Breiner was playing both sides in Masunaga’s criminal case.

This was one of the most problematic aspects of the case for Harrison when he took over Masunaga’s case from Breiner in late 2016. He said it didn’t matter that Breiner had both Kealoha and Masunaga sign conflict of interest waivers.

“To me, this was probably the most obvious and egregious conflict an attorney could get into,” Harrison said.

“How can you be zealous in the advocacy of your client when you’re representing both the prosecutor and the defendant and the prosecutor has an interest in your client because your client has damaging information regarding a family member?”

Federal prosecutors, too, worried about Breiner’s conflicts in the case.

After they indicted the Kealohas, they filed a motion to have Breiner kicked off the case. They said among other things that his relationship with the Kealohas was fraught with conflicts of interest, some more serious than others.

Federal investigators filed court documents alleging Kealoha passed along a confidential informant’s name to Breiner so that he could then relay that information to his client in the gambling case.

That client, Tracy Yoshimura, eventually told federal investigators that he believed Kealoha wanted to curry favor with Breiner so that he would represent the Kealohas in the federal corruption case.

Yoshimura said at the time he was blown away that a city prosecutor would reveal the name of an informant to anyone, much less a criminal suspect in an ongoing case. “I know that people can get murdered for that,” he said.

“I stand by the work that I did for Tiffany Masunaga based on the information that I had at that time.” — Myles Breiner

The government’s motion to disqualify Breiner also highlighted his potential conflicts in the Masunaga case.

In particular, prosecutors pointed out that during one proceeding Breiner and Kealoha had participated in an “off the record” conversation with Rom Trader, who was a judge in the case.

They also mentioned that Kealoha herself was having secret conversations with Masunaga while she was actively prosecuting her on drug charges.

According to federal prosecutors, Kealoha began sending Masunaga encrypted text messages via Signal as a means to avoid detection from anyone who might be peeking in.

In court documents, federal prosecutors say they recovered more than 500 pages of messages from these surreptitious communications, including several exchanges from July 26, 2016.

“You are such a good person, now we need to vindicate you on many levels, while we have them be accountable!!!” Kealoha wrote to Masunaga.

“Just remember that I always got ur back, I love you and will protect you always!!!”

That same day, Masunaga told Kealoha that Breiner had called her to discuss a change of plea in the case.

“Omg, ruler of the world #ROW.” Kealoha wrote.

“Go TEAM!” Masunaga said.

“GO TEAM!!!” Kealoha echoed. “Can’t wait for this shit to be over.”

“Ditto,” Masunaga responded. “Then we’re free.”

In an interview with Civil Beat, Breiner said he did not want to discuss the details of Masunaga’s case, the federal government’s 2017 motion to disqualify him or the recent indictment of Kealoha and her brother.

“I stand by the work that I did for Tiffany Masunaga based on the information that I had at that time,” Breiner said.

“The plea agreement allowed her to avoid any type of conviction.”

Keeping Masunaga Under Wraps

Tiffany Masunaga’s change of plea came on Sept. 9, 2016, but it was a secretive affair, and one that city prosecutors wanted to keep that way.

Deputy Prosecuting Attorney Chasid Sapolu, who had taken over the case from Kealoha, convinced Circuit Court Judge Rom Trader to seal the entire case file, saying that it was important to protect the safety and privacy interests of the state’s witnesses.

Trader, a former city prosecutor, initially agreed, which effectively hid the entire case file from public view. He later backed off the blanket secrecy to limit the sealing only to Masunaga’s plea.

What remained hidden, however, was a confidential cooperation agreement between Masunaga and the prosecuting attorney’s office that was signed on Oct. 6, 2015, by Masunaga, Breiner and Keith Kaneshiro.

That agreement kept Masunaga out of the jail, but it also effectively silenced her.

The document stated that Masunaga would be asked to provide information about police corruption and other criminal activity in exchange for leniency in her drug case and immunity from other charges that might arise due to her cooperation.

Another provision said she could could speak to other law enforcement agencies, but only with the express permission of the prosecuting attorney’s office.

The drug charges, meanwhile, never disappeared.

Masunaga’s case remains open — even now — despite the fact her co-defendant Alan Ahn pleaded no contest in February 2017 and has already served his time.

William Harrison said Masunaga was never asked by city prosecutors where she got the drugs, despite having a cooperation agreement.

That bothered Harrison, who spent nearly two years trying to recuse city prosecutors from the case. It also raised questions about whether officials in the office were trying to protect Kealoha and, by extension, her younger brother, Rudolph Puana.

City prosecutors kept Masunaga’s cooperation agreement hidden for years.

But that changed in 2018 after the Hawaii Supreme Court sided with a Civil Beat reporter who had argued to have the documents unsealed.

The Feds Find A ‘Fabricated Investigation’

It was a speeding ticket that led federal investigators to Kealoha and Puana’s alleged drug conspiracy.

That’s because Masunaga and her case were folded into what prosecutors say was another “fabricated investigation.”

On Aug. 12, 2014, Honolulu police officer Ty Ah Nee pulled over Adam Wong for driving 78 mph in a 35-mph zone near the Wilson Tunnel on the Likelike Highway.

The next month Kealoha, who was a supervisor in the career criminal division overseeing the prosecution of felons and repeat offenders, went to traffic court to have the case dismissed.

She told the judge that Wong wasn’t the person behind the wheel, and that instead it was a “career criminal” who was in possession of both Wong’s truck and drivers license.

Kealoha said the real perpetrator — the one who was apparently impersonating Wong and driving his truck — was already in custody. The judge dismissed the ticket.

But federal investigators say Kealoha lied in court.

Wong was an electrician, and at the time Kealoha got his ticket dismissed, federal prosecutors say, she was trying to enter into a business relationship with him as part of a massive solar farm project.

The case took a strange turn in 2016 when it was revealed in the media that a federal grand jury was investigating the dismissal as part of a larger inquiry into corruption within HPD and the prosecuting attorney’s office.

Honolulu Prosecuting Attorney Keith Kaneshiro publicly defended Kealoha’s decision to dismiss the ticket, including in an interview with Civil Beat.

But he told a much different story about the dismissal than the one Kealoha gave the judge.

Kaneshiro said he ordered Kealoha to dismiss the speeding ticket as part of a larger investigation into “ghost tickets.”

He said Wong had told his office that he never received the ticket from Ah Nee, and Kaneshiro said that led to an investigation into whether HPD officers were writing fake citations to motorists in an attempt to get called to court to collect overtime pay.

Kaneshiro told Civil Beat that Wong had also signed a cooperation agreement with his office, but he refused to provide any documentation proving its existence.

Even when defense lawyers began asking prosecutors in his office for evidence of the investigation as it related to Ah Nee, they said in court filings that there was none.

Recently filed records say that when the FBI began investigating the ticket fixing, Kealoha “immediately took steps toward legitimizing her deceitful behavior.”

The filings say Kealoha sent emails from colleagues’ computers to misdirect the investigation, concocted a fake cooperation agreement with Wong to cover for the dismissal and opened a state investigation into supposed police corruption.

That secret investigation alleged, among other things, that Ah Nee, the officer who pulled over Wong, was involved in a “ghost ticket” scheme.

Kealoha wasn’t alone in her investigative endeavors. Kaneshiro launched a secret investigative grand jury to sniff out the alleged corruption in HPD.

One of his witnesses was Tiffany Masunaga.

Although she was arrested with a Honolulu police officer in a house full of drugs, Harrison said the prosecutors never asked her where the contraband came from.

Instead, he said, they wanted her to tell them everything she knew about corrupt police officers.

But what stuck out most, Harrison said, was who was in the room as Masunaga testified before the grand jury.

Harrison was there on that day and he saw some of Kaneshiro’s top deputies go in and out of the room, including Jan Futa, Armina Ching and Chasid Sapolu. Even more striking was the fact that Kaneshiro himself was there.

Harrison said he’s been working as a defense lawyer for more than three decades and he’d never seen anything like it.

“You would not normally see the top three or four prosecutors in your office at a grand jury proceeding,” Harrison said. “I could see that maybe if they were looking to prosecute the governor or someone like that, but not in this kind of case, one where it’s just run-of-the-mill ticket fixing.”

Harrison, however, demurred when asked if he thinks Kaneshiro could have known Kealoha was trying to protect her younger brother.

“I can’t answer that question because of the ongoing investigation,” Harrison said.