PĀ‘IA — At a campaign event in Pā‘ia on Wednesday night, Maui County Mayor Richard Bissen told a crowd of supporters that elected office is “more brutal” than the nearly 35 years he spent as a prosecutor and chief judge of Maui’s 2nd Circuit Court.

“In court, you can fight back against the guy,” Bissen said. “Because … at the end, everybody gets their turn, and then the jury or the judge decides. You run for election, the guys can just sniper from far away.”

In 2022, Bissen was a political newcomer who ousted incumbent mayor Michael Victorino. Now, as the incumbent, he is preparing to defend his seat and his first term against a slate of challengers and a lawsuit filed last week by his former chief of staff alleging retaliation for reporting suspected fraud. Bissen denies the claims and says the lawsuit is “100 percent” politically motivated as he runs for reelection. 

“I think it was filed in order to impact the outcome,” he told the Hawai‘i Journalism Initiative on Wednesday night. “I think it’s too strong to be a coincidence.”

Eight people have pulled papers for the mayor’s race — including Bissen, who announced his reelection campaign in November — but only Justin Herrmann had filed as of Friday. In January, Maui County Council Vice-Chair Yuki-Lei Sugimura and former Maui Planning Commissioner P. Denise La Costa also publicly announced bids for mayor.

The filing deadline is June 2, with the primary election on Aug. 8. 

Hawai‘i political analyst Colin Moore said the lawsuit could loom over the election but ultimately may not be a deciding factor.

“It’s not unusual to get these sorts of lawsuits against senior county officials,” Moore said. “But it certainly doesn’t help this reelection campaign, especially to have a lawsuit filed by a former chief of staff. That’s as high level as it gets.”

On April 24, Bissen’s former chief of staff Leo Caires filed a lawsuit in 2nd Circuit Court alleging that the county wrongfully terminated him after he reported questionable financial activities by other county employees. 

Caires was sworn in as chief of staff in January 2023. He was someone that Bissen said he considered a friend. But Caires says the trouble started when he began looking into a “suspicious” Aug. 16, 2023 invoice for $45,532.32 from a company called RTFEX Depot in March 2024.

Noticing discrepancies in the invoice, Caires said he tried to dig into the Scottsdale, Ariz., business but couldn’t verify the company’s address or existence. His investigation led him to believe that an executive assistant of Bissen’s known as “MA,” or “Pono,” and an Office of Economic Development grant recipient known as “AVS” had “likely submitted false cashiers’ checks made out to a fake company to the OED for reimbursement.”

Caires said he called MA, who said he had “received the equipment he purchased from RTFEX Depot from a third party at the parking lot of Target in Kahului” but did not specify the third party or provide documents to back up the transaction.

The lawsuit alleges that when Caires told the mayor he thought there should be an investigation, “Mayor Bissen got upset at Mr. Caires and ordered him to stop.” MA was later reassigned to a position in the Office of Economic Development but eventually resigned, according to court documents.

The lawsuit also claims that Caires discovered that the Office of Economic Development director at the time, Luana Mahi, “appeared to be inappropriately using her position” to benefit family members. Caires said he questioned a grant after noticing the registered business address was that of Mahi’s husband, her son’s business and the business that she owned before working for the county. 

Mahi was placed on paid leave in August 2024 pending an investigation. She was fired months later, and the case is now with the state Attorney General’s Office, according to county spokesperson Laksmi Abraham.

In a statement on Friday, Bissen said: “The allegations made by Mr. Caires are false.”

“I am confident that overwhelming, credible evidence will reveal the many inaccuracies presented in this unfounded complaint,” he said. “I welcome the opportunity to present the full record in a court of law, where facts, not claims, will determine the outcome.”

Bissen said Wednesday that “on the advice of my attorney, I cannot get into the facts about what happened” but said that the issues Caires claims to have found “were identified by other people.”

“What we did was an internal investigation that was brought to our attention by the people who handled the paperwork, not by him,” Bissen said.

After reporting his suspicions, Caires said his duties were “steadily reduced” before he was demoted to energy commissioner around October 2024. He said he suffered health issues “stemming from the retaliatory acts from the County and Mayor Bissen” and returned from a period of medical leave on or around Dec. 23, 2024, to find a letter from Bissen dated Dec. 18, 2024, stating that he would be terminated on Jan. 15, 2025. 

Bissen said that he tried to support Caires but eventually he “was let go because he could not meet the requirements of the job and not for any other reason.” 

Joseph Rosenbaum, Caires’ attorney, declined to respond to Bissen’s comments.

In his statement, Bissen said Caires’ attorney had made “an excessive monetary demand of taxpayer funds for settlement” in April 2025 that the county “firmly rejected.” The county declined to provide the amount. 

In June, the council voted to retain the law firm of Marr Jones & Wang for up to $350,000 to represent the county in “pre-litigation negotiations and litigation” regarding Caires’ allegations.

“It is no coincidence that Mr. Caires chose to release this complaint to the media nearly a year later,” Bissen said. “The timing appears intended to distract the public and cast doubt on the work being done on behalf of our community. This is reflected in the unusual step of issuing a press release rather than allowing the facts to be addressed through the court process.”

During the campaign event, Bissen also said that the county is shifting the Office of Economic Development’s focus from grants to “developing the economy” in key areas such as construction, technology and the creative industries. 

When asked afterwards if the shift in focus was related to Mahi and the recent grant issues, Bissen said, “No, we would’ve done this either way.”

“We’re just trying to make it more efficient so that there’s less things can go awry,” he said.

Caires’ lawsuit also pointed to a report released in February by independent contractor Spire Hawaiʻi LLP that found the county did not have adequate fraud risk controls in place. The county has disputed aspects of the report but said fraud risk management measures are already underway.

Moore, who’s also an associate professor with the University of Hawai‘i Economic Research Organization, said that the lawsuit likely won’t be settled very quickly and will “just linger.”

“Any kind of controversy going into a competitive reelection is never good,” Moore said. “It just means that it’s going to introduce questions in voters’ minds about the integrity of the information of the administration, whether it’s fair or not.”

But, he added, “is it a catastrophe? No.”

Incumbents like Bissen have a big advantage in that everyone knows who they are, Moore said. But being so well known to voters can also prove a challenge.

“For the most part, they’ve made up their mind whether they like you or they don’t, which means there’s not much in a campaign you can do to really shift opinion,” Moore said. 

That’s especially tough for a mayor who “has presided over a really controversial period” like the fire. But, Moore said, that also means “he clearly understands where his vulnerabilities are and what he’s done that people don’t like. And that at least allows him to prepare for that in the campaign.” 

Given the difficult period Maui has gone through over the last few years, Moore said it’s possible that Bissen could face the “anti-incumbent vote.” His 2022 win over Victorino proved that Maui voters “are perfectly happy to throw an incumbent mayor out.” Regardless of the outcome, Moore said he expects the mayor’s race to be a close contest with high spending.

“It’s probably the most interesting race this election cycle,” he said.

As the mayor’s race unfolds, Sugimura said she planned to let the legal process play out.

“I trust the courts and the process afforded to all parties involved,” Sugimura said via text. “I am busy focusing on the County’s budget and running a good campaign and finding ways to keep Maui Nui, Maui Nui.”

La Costa said “as far as the timing (of the lawsuit), I don’t know if that was contrived to be a disruption.”

However, she said, “it makes me feel very uncomfortable about the openness, the truthfulness and honesty” of the administration. She said if she becomes mayor that transparency is “one of the things that I’m just so dead set on.”

“You want something in public records? Come in and look,” La Costa said.

La Costa said the way the county has handled Lahaina’s recovery from the fire is also the reason she’s running. In 2018, a fire in Kaua‘ula Valley came within a quarter-mile of her Launiupoko property, and in 2023, the smoke and ash from the Lahaina fire filled her home. 

“My town is still in shambles and my friends are leaving,” La Costa said. “Because they have no jobs, they have no businesses. … I can’t stand nothing being done anymore.”

Herrmann did not respond to a request for comment by Friday. 

When asked Wednesday how he thought the county’s response to the fire would impact his election chances, Bissen said voters’ perspective likely depends on where they’re at in the rebuilding process. Those whose homes are rebuilt may be happy with the recovery so far. Others who are still waiting may think negatively of the county.

According to Maui County’s recovery dashboard as of Monday, 310 homes are currently under construction. A total of 561 building permits have been issued, with 188 buildings completed, and another 353 being processed.  

“I know everybody’s working as hard as possible — that I know,” Bissen said. “And we’re giving it our best, and we’re going to continue to. We’re not slowing down.”

After Caires’ lawsuit, Bissen expected more challenges on the campaign trail but said Friday that “I have spent my life serving, protecting and defending our community with integrity and accountability, and I will not be deterred by efforts to undermine that work for personal or political purposes.”

“As my administration moves forward, taking on entrenched interests, and advancing long-overdue change, we expect to see misinformation and negative attacks from those who do not share our vision,” he said. “We will not be distracted.”