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A disgraced former Honolulu prosecutor won a bet against fellow drug users by taking a photo with a line of cocaine on her police chief husband's desk, according to newly filed court documents. 

Katherine Kealoha, 50, former deputy city prosecutor, and her now-estranged husband, former Police Chief Louis Kealoha, 60, were both convicted at trial in 2019 of conspiracy, obstruction and bank fraud, and sentenced last fall to 13 years and seven years in federal prison, respectively.

The one-time Honolulu power couple were at the center of a sprawling, years-long  corruption case involving a drug-trafficking ring that was operated by Kealoha's anesthesiologist brother, Dr Rudolph Puana, according to federal prosecutors. 

Disgraced former Honolulu prosecutor Katherine Kealoha (left) once took a picture of a line of cocaine on the desk of her police chief husband Louis Kealoha (right), according to new court records 

Puana, who was addicted to cocaine, is accused of funneling large quantities of opioids from his pain management clinic to his prosecutor sister and other friends, who traded the prescription medications for cocaine and cash. 

Kealoha has already pleaded guilty to charges related to her role in her brother's drug distribution ring, including covering up Puana's alleged crimes by coercing a suspected drug dealer into lying about the source of the narcotics found in the woman's house during a police raid. 

Katherine's brother, anesthesiologist Rudolph Puana, faces dozens of counts of distributing controlled substances, including oxycodone and fentanyl

As part of her plea deal in October 2019, Kealoha admitted she arranged to have herself assigned as the prosecutor overseeing the investigation of her brother’s co-conspirators, and that she cultivated a close relationship with suspected drug dealer Tiffany Masunaga to reduce the likelihood that she would reveal Puana’s role in the drug conspiracy, reported Hawaii News Now. 

'I always got ur back, I love you and will protect you always!!!' read one private text message Kealoha sent to Masunaga. 

'GO TEAM!!! Can’t wait for this s*** to be over,' read another, to which Masunaga replied, 'Ditto[.] Then we’re free[.]' 

According to documents filed on Monday in US District Court for the District of Hawaii, between 2012 and 2017, Puana handed out a quarter of all his oxycodone prescriptions - some 7,000 pills - to his close friends for distribution in order to support his cocaine habit. 

'Puana’s use of controlled substances spiraled to the point of challenging his fellow users to take a photo of themselves using cocaine in an outrageous place,' the filing states. 'Puana’s sister, Katherine Kealoha, "won" by submitting a picture with a line of cocaine on the desk of the Honolulu Police Chief, Louis Kealoha.'

Former Chief Kealoha is pictured with his brother-in-law Puana, who is set to go to trial in September 

Puana faces dozens of counts of distributing controlled substances, including oxycodone and fentanyl, health care fraud and being an addict in possession of firearms. 

Puana's trial is scheduled to get under way on September 14. Kealoha is expected to testify against her brother. 

Kealoha, 60, was convicted at trial in 2019 of conspiracy, obstruction and bank fraud, and was sentenced to seven years in prison 

For years, Louis Kealoha, Honolulu’s surfing, Rolex-wearing police chief, and Katherine Kealoha, his deputy city prosecutor wife who drove a Maserati and led an elite unit targeting career criminals, were widely respected as the city’s Native Hawaiian role models who hailed from humble, blue-collar roots and rose to the top thanks to decades of hard work. 

They lived in a swanky house near an exclusive country club in the city’s Kahala neighborhood, sometimes called Honolulu’s Beverly Hills, .

But then the facade started to crumble. The Kealohas were so desperate to fund their lavish lifestyle, prosecutors said, they swindled more than a half-million dollars from banks, relatives and others. Their charmed lives turned into a twisted tale of allegations of fraud, illegal drugs and family turmoil.

Federal authorities started investigating the two in 2015, and both stepped down from their jobs as the probe deepened.

The case has morphed into a scandal characterized as the largest corruption prosecution in Hawaii history, and prosecutors say greed was the couple’s motive.

'Public embarrassment was not something the Kealohas could afford. They needed to maintain their carefully crafted public image,' federal prosecutors said in court documents.

The beginning of the end for the Kealohas, prosecutors said, came in the unlikeliest of ways: a botched plot to frame a relative for a mailbox theft

The Kealohaa' charmed life began unravelling after they attempted to frame a relative for the theft of a mailbox from their $1.3million home (pictured) 

Katherine's grandmother and her uncle threated to expose her and her husband for fraud, so the prosecutor tried to declare the elderly woman incapacitated and frame the uncle for theft 

Prosecutors said Katherine's uncle and grandmother had threatened to expose them for fraud stemming from a $200,000 reversed mortgage scheme and a real estate transcation, so she devised a scheme to silence them. 

She tried to have her now-deceased 99-year-old grandmother declared incapacitated. She and her husband used members of a special, hand-picked police unit to frame the uncle, Gerard Puana, for stealing a mailbox from Kealohas’ $1.3million home, prosecutors said.

Puana was arrested, and his federal public defender, Alexander Silvert, was initially skeptical about his client’s seemingly outlandish claim that he was being set up. It seemed too bizarre: The idea that Honolulu’s law enforcement power couple would hatch such a scheme to discredit him because he had accused his niece of trying to steal money.

But the couple made a big mistake, Silvert said: They reported that the mailbox was valued at $380, but Silvert and his investigators learned it cost only $180. The difference in value allowed Puana to be charged with a felony instead of a misdemeanor.

'When I realized they were lying about the make and model of the mailbox, then I was "OK, there’s something going on,”' Silvert said.

Puana’s mailbox theft case ended in a mistrial in 2014. In 2015, a jury sided with Katherine in the civil lawsuit her grandmother and uncle lodged against her.

Federal investigators stepped in, eventually revealing allegations against Kealoha, including stealing $160,000 from the trust funds of two children, showering money she bilked on her firefighter lover Jesse Ebersole and the alleged drug-dealing with her brother. They alleged she even invented an alias — Alison Lee Wong — 'to dodge scrutiny, forge documents, secure state Senate confirmation, and more.'

In 2017, she and her husband were indicted on the federal criminal charges.