Keith Regan was running a Maui trucking company in the early 2000s when Alan Arakawa, then a member of the Maui County Council, asked him a simple question: “Is your passion really as an entrepreneur or is your passion somewhere else because you’re really involved in community-related-type activities?”

Regan had launched Hawaiʻi Cartage Inc. in 1995, his first business out of college, according to his online resume. But the thought-provoking conversation with his future boss sparked a transition to a long career in public service, beginning on Maui.

Since then, Regan has held several high-level leadership positions, first in Arakawa’s administration during his three terms as Maui County mayor and later in state government on Oʻahu.

And now, at age 54, Regan is the unexpected acting lieutenant governor of Hawaiʻi, second in command only to Gov. Josh Green.

Regan was appointed by Green on April 23 after Senate President Ron Kouchi, House Speaker Nadine Nakamura and Attorney General Anne Lopez declined the temporary position, which became available when scandal-plagued Sylvia Luke took an indefinite, unpaid leave of absence amid a bribery investigation that Lopez is overseeing.

But it’s a role Regan expects to keep for only a few months, while he also juggles his duties as the state’s comptroller and director of the Department of Accounting and General Services, a sprawling department with eight divisions and at least a dozen agencies, boards and commissions. 

Regan said he does not plan to run for the permanent position in the August primary, acknowledging he’s more of an operations guy than a politician.

That was on display in 2016, when he campaigned unsuccessfully for the Wailuku residency seat on the Maui County Council, finishing third in the primary election.

Arakawa said Regan is a go-getter who is “very good with people and ideas,” but not a natural politician, something that fellow county officials also noted.

“It was clear to me that being a candidate wasn’t where he was most comfortable,” said Teena Rasmussen, the county’s former director of economic development who worked with Regan for eight years. “He seemed stiff, uneasy in the spotlight, and it simply didn’t feel like a natural fit for him.”

Some people are born for the political stage. Others excel behind the scenes. Regan is more the latter, in her view.

“Keith has found his niche with these high-level administrator positions he has taken,” she said. “His higher education, his analytical mind, his in-the-trenches experience, and steady demeanor make him perfectly suited to manage these behemoth departments that we have in the state.”

Hawai‘i needs more people like Regan “who are willing to take tough and unglamorous jobs to improve the functioning of government,” Rasmussen said.

Regan said his passion is public service. He served under Arakawa as finance director from 2003-2004, and later as managing director from 2004 to 2007 and again from 2011 to 2018.

In Regan, Arakawa saw someone with potential who could complement his skill set.

“We helped each other,” Arakawa said. “I’m older than Keith. I had the experience factor. He had the new technology factor.”

When Arakawa reached term limits, Regan moved to Oʻahu at the end of 2018 to serve in top state government positions, starting as chief administrative officer with the Hawaiʻi Tourism Authority before switching to business management officer for the Department of Commerce and Consumer Affairs and now as state comptroller.

“I enjoy the work immensely,” Regan said.

By all accounts, the empty-nester father of one appears to live and breathe his career. Lynn Araki-Regan, his spouse of 23 years, said he’s “tireless.”

“He puts in a lot of time,” she said. “He goes to work early, works even evenings. When I’m watching TV at night, he’s often receiving calls.”

While filling in for Luke, Regan is dealing with new constitutional and statutory responsibilities that include certifying name changes and authenticating official state documents like birth certificates and divorce decrees. 

He now oversees her staff of 17, and also is in charge of supervising certain administrative state functions, handling some intergovernmental relations, attending official events, serving as a bridge between the executive and legislative branches, keeping Luke’s signature Ready Keiki program moving forward, and other duties as assigned by Green. 

Most importantly, the lieutenant governor usually takes charge of the state when the governor is away, incapacitated or otherwise unable to perform official duties. 

Regan said it’s always in the back of his mind that this might happen. 

“If I’m called upon to serve in that capacity and to support the governor and the state in that regard, that’s something that I’m going to have to consider and I’ll have to step in and do what the governor is asking me to do,” Regan said.

But Green has the option of appointing someone else.

“There are others in front of me who have that opportunity to accept that role,” he said. “That includes the attorney general, the director of finance and then myself.”

The governor is comfortable with Regan in charge should he have to travel out of state, Green’s spokeswoman said. 

That’s different from February when Green said he wouldn’t leave Hawai‘i, at least for that month, given that Luke revealed she was the target of a bribery investigation by the Hawai‘i Attorney General’s Special Investigations and Prosecution Division. The criminal probe continues to look into a $35,000 donation to an influential Hawai‘i politician in 2022.

In addition to taking a leave of absence, Luke said she will not seek reelection. Six candidates have pulled papers so far to run for lieutenant governor, including Kauaʻi County Mayor Derek Kawakami, though none have filed ahead of the June 2 deadline.

Makana McClellan, Green’s director of communications, said Regan brings to the job decades of leadership and operations experience in government.

“With the acting lieutenant governor structure formally in place pursuant to state law, the administration is confident that continuity of government and day-to-day operations will remain steady during any temporary absence by the Governor,” McClellan said.

Green is not considering asking Luke to resign, she added. 

“He continues to believe that due process should be respected and any review or investigation should proceed independently, expeditiously and without political interference,” McClellan said.

MAUI BEGINNINGS

Regan was born and raised in North Andover, Mass., but moved to Maui with his family at age 17, straight out of high school in 1988. 

His father had worked for the U.S. Environmental Protection Agency as a brownfields expert, overseeing the remediation of polluted sites in New England. His parents decided to move from one side of the country to the other to start a new life after visiting the Hawaiian island and falling in love with its natural beauty, Regan said. 

He met his wife through their mutual involvement with the Kiwanis Club. Araki-Regan said her family on Maui goes back eight generations to when her ancestors moved from Japan for plantation work on the island.

Regan, who has master’s degrees in business and public administration, now starts his workday at 6 a.m., spending the first few hours attending to responsibilities at the Department of Accounting and General Services on Punchbowl Street. He then heads over to Luke’s conference room in the Hawai‘i State Capitol building and spends the next several hours fulfilling lieutenant governor duties.

He generally leaves the office between 4:30 and 5:00 p.m., heads home for dinner with his wife and works remotely for another few hours before calling it quits.

With their only child poised to graduate from UCLA in June, the work-oriented couple is digging into their high-powered careers. Araki-Regan, an attorney, holds a high-level position running administrative services at the state Department of Labor and Industrial Relations. 

She previously served as Hawai‘i’s state tax collector, first deputy director in the Transportation Department, and like her husband, held top jobs in Maui County government, including as Arakawa’s chief of staff, budget director and acting managing director. 

During his time as managing director for Maui County, Regan vastly improved the functioning of the Department of Motor Vehicles, instituting a number system and lanes based on the requested service. Prior to his reforms, everything was first-come, first-served.

Before the changes, Rasmussen said: “The lines would be out the door. They’d make you wait in the sun.”

Former County Council member Kelly King, who is planning to run again for the South Maui seat, said Regan saw value in proposed reforms she championed to institute an elected governing body that would hire a professional county manager, someone who would stay on regardless of who occupied the mayor’s office.

The goal was to have professional administrators rather than political appointees manage county operations. 

“Keith was very supportive,” King said. “Personally, I liked him.”

In 2022, four years after Regan and Arakawa left the county, Maui County government was rocked by a major bribery scandal when former director of the Department of Environmental Management Stewart Stant, who was appointed by Arakawa in 2015, pleaded guilty to accepting bribery payments of up to $2 million from businessman Milton Choy in exchange for Stant directing nearly $20 million in sole source contracts and purchase orders to Choy’s wastewater company. Stant pleaded guilty and a judge sentenced him in 2023 to a 10-year prison term and ordered him to pay nearly a $2 million judgment. 

Regan and his wife denied having any knowledge of Stant’s crimes while they served in the Arakawa administration.  

“Absolutely not,” Regan said. “And if we had any inkling that that was going on, we would have immediately investigated it without question.”

WALKING THERAPY

Despite their demanding jobs, Regan and his wife make sure to spend time together daily, often walking hand-in-hand for 30 minutes through the streets of their Honolulu neighborhood.

The couple also hosts a podcast they started in 2025: “Life, Leadership and Love.” In a recent episode, they described why walking together is important.

“I feel like I can clear my mind, and get some really good advice, and really just prepare myself for whatever might be coming the next day,” Regan said. “It’s very healthy for me.”

He described the daily movement sessions with his wife as “almost like a walking therapy session.”

The couple discusses any work or personal challenges they’re grappling with. Or, they just share what’s on their mind.

“Maybe we had an excellent day, and we just want to share the good news of our day,” Araki-Regan said. “But that 30 minutes, besides walking and increasing my number of steps on a daily basis, I look forward to our discussion, because I feel like we have each other’s attention for half an hour, and we can confide in each other.”