Two Honolulu police officers told a jury Thursday that they witnessed then-Honolulu Deputy Prosecutor Katherine Kealoha insert herself into an investigation involving her brother, who is on trial for allegedly running a prescription drug ring.

The testimony came on the third day of the federal criminal trial held in U.S District Court in Honolulu of Rudolph Puana, a Big Island anesthesiologist accused of writing opioid prescriptions for his friends to either sell or trade for cocaine.

Kealoha is serving a 13-year sentence at a federal prison in California on corruption charges involving Puana and Kealoha’s estranged husband, ex-Honolulu police chief Louis Kealoha. However, she is listed on the prosecution’s witness list and is expected to testify in coming days.

Katherine Kealoha already has pleaded guilty to helping her brother avoid prosecution in the drug case. The witnesses on Thursday testified that the then-deputy prosecutor was so involved that she showed up in person during a drug raid being conducted in 2015 as part of the investigation.

“I’ve never had a prosecutor show up at the scene of an enforcement activity,” HPD Sgt. Grant Jhun, a narcotics and vice officer, told the court.

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, although he pleaded guilty to the lone gun charge the day before his trial began.

The day began with testimony from Puana’s childhood friend and well-known local writer Christopher McKinney, who said that he would sell oxycodone pills prescribed by Puana for $15 each. McKinney said he would also obtain cocaine from Tiffany Masunaga, who was dating HPD officer Alan Ahn, and brought Masunaga fentanyl patches given to him by Puana in 2015.

McKinney, who signed an immunity agreement with prosecutors in exchange for his testimony, said he believed Puana was aware that he brought the fentanyl patches to Masunaga but said Puana did not give him any direction on what to do with the opioid patches.

Those fentanyl patches were later allegedly found during a raid at Masunaga’s home on Aug. 12, 2015, following an investigation that began with a tip Puana gave to HPD Sgt. Daniel Sellers.

Sellers pleaded guilty in 2019 to federal charges for helping Kealoha and her then-police chief husband frame a family member for the theft of their mailbox in a separate case.

Sellers said he first met Rudolph Puana and Christopher McKinney when he was dating Kealoha during their school years.

He then rekindled his relationship with Puana in 2015 after running into him and McKinney as they were celebrating the launch of a book collaboration, “The Red-Headed Hawaiian,” which was about Puana’s life.

Sellers said he had dinner with Puana in July 2015, and Puana eventually told him that Masunaga was dealing drugs out of her Waiola Street home where she was living with Ahn.

Sellers said he later informed Katherine Kealoha that her brother was having substance abuse problems and told her about McKinney, Ahn and Masunaga.

Sellers said he then set up a meeting with Puana and McKinney to corroborate the tip but was surprised to see that Kealoha also was there. “Despite her being there we continued to have this meeting,” Sellers said. “I just thought she was called because she was the older sister.”

Sellers said he then met with a supervisor and Kealoha and decided to begin an investigation into Masunaga and Ahn. He added that they decided having a prosecutor there would expedite the process, but he did not think that prosecutor would be Kealoha because of her senior level.

Jhun said he was told he would be working with Sellers and that Sellers had a confidential informant, although Jhun was never told the identity of the informant. Jhun added that neither McKinney nor Puana’s name came up during the initial stages of the investigation.

“We followed Alan Ahn with Tiffany Masunaga around town and we observed drug transactions,” Jhun said.

Meanwhile, Sellers and the criminal investigation division were doing the same until they witnessed what they believed was a drug transaction outside Masunaga’s home in August 2015.

Police stopped the man and found cocaine in the paper bag, then persuaded him to cooperate in the investigation, Jhun and Sellers said.

Sellers said he told Kealoha that it would be good to have a prosecutor come to the scene to offer the driver immunity. “I did not think it was going to be her,” Sellers told the jury.

Jhun testified that he was also struck by Kealoha’s presence at the scene when she arrived.

The cooperating witness got in the backseat of a vehicle with Kealoha. Sellers was in the driver’s seat but said he got out after a few minutes, leaving Kealoha alone with the man.

Hours later, a SWAT team descended upon Masunaga’s home, where police found cocaine, prescription pills, and more than 100 fentanyl patches.

Kealoha then showed up to that scene as well, which Jhun told the jury he thought was odd.

The investigation stalled after the raid, according to Jhun. He testified that he then learned that Kealoha, Masunaga and Masunaga’s attorney, Myles Breiner, were holding meetings without HPD officers present.

“At some time, I was given a call by Katherine Kealoha who asked if I was busy,” Jhun said. “I said no, (and she said) ‘I have something to give you.’”

Kealoha then met with Jhun and gave him what he recognized as a transcript from one of the meetings, and he noticed something odd at the end of the document.

“The transcript showed that Tiffany Masunaga and Kat Kealoha knew each other,” Jhun said, adding that he was instructed to stand down and stop working on the investigation a short time later.

Sellers, too, said his involvement in the case ended toward the end of 2015.

Masunaga would ultimately avoid conviction on numerous drug charges. Ahn pleaded no contest and was sentenced to 60 days in jail and four years of probation.

Puana’s trial was set to resume Friday morning.