With top leadership positions up for grabs, the political makeup of the City and County of Honolulu is set to experience a rare overhaul. 

Honolulu Mayor Kirk Caldwell is term-limited as are five of the City Council’s nine members: Kym Pine, Ikaika Anderson, Ann Kobayashi, Joey Manahan and Ron Menor. Prosecuting Attorney Keith Kaneshiro, who has been on paid leave for over a year amid a federal investigation, is not running for reelection. 

While turnover in city politics isn’t unusual, it is not often voters can choose a new mayor, prosecutor and council majority all at once, said Colin Moore, director of the Public Policy Center at the University of Hawaii. 

“The whole nature of city politics will be transformed after November,” he said. “It presents a real opportunity for people who are frustrated with incumbents.” 

Mayor Kirk Caldwell announces lawsuit against large petroleum companies seeking damages for climate change at Waikiki Beach today.
Mayor Kirk Caldwell, at the mic, and five of the city’s nine council members will be out of a job in January. They’re all term-limited. Cory Lum/Civil Beat

The open prosecutor’s seat is a chance for new leadership in an office that has been passed back and forth between only two people – Kaneshiro and former Prosecuting Attorney Peter Carlisle, who also served as mayor – since 1989. Prior to that, Charles Marsland held the post for two terms. 

There have been only three men to hold that office since 1981,” Moore said. 

Just because people will gain new titles doesn’t necessarily mean the city will be getting new blood. Several candidates for office are familiar faces in local politics and are running on their experience. 

The mayoral candidates include former Mayor Mufi Hannemann; Colleen Hanabusa, a two-time congresswoman; and Pine, a councilwoman and former state representative.

Acting Prosecuting Attorney Dwight Nadamoto, who Kaneshiro appointed to head the office when he went on paid leave, is seeking to keep the post permanently. Retired Judge Steve Alm is among those challenging him.

State Rep. Calvin Say, who has represented the Kaimuki and Palolo area for over 40 years, is making a run to replace Kobayashi on the council. And Will Espero, a former state senator, is running to take over from Menor. 

Colourful overlapping silhouettes of people voting in USA elections
This is Hawaii’s first election with all-mail voting. Getty Images

Since traditional campaigning has been upended by the COVID-19 pandemic, Moore said well-known candidates have a special advantage this season because of their name recognition. Plus, voters may be looking for experienced and perhaps older candidates who they feel are best equipped to guide Honolulu out of the current financial catastrophe.

But the ballot will also include first-time candidates who argue they can provide a fresh perspective. 

In the mayor’s race, former television executive Rick Blangiardi led a recent Civil Beat/Hawaii News Now poll with 21% of support among potential voters. The political newcomer is backed by former Republican Gov. Linda Lingle and has secured an endorsement from the police union. During a candidate forum last week, he said that he is not “building a political career.”

Businessman Keith Amemiya has pegged himself as an outsider too, although his campaign contributions list resembles that of a much more seasoned candidate. Amemiya is backed by the the state’s largest public workers union.

Criminal defense attorney Megan Kau, a first-time candidate for prosecutor, bested her better-known opponent Alm in fundraising earlier this year.

At the City Council, several legislative staffers are running to replace their current or former bosses.

Kathy Davenport, an Air Force veteran and former council staffer, is running to take over from Pine in District 1 covering Ewa Beach, Kapolei and Waianae. Her opponents include Anthony Paris, an analyst for the Iron Workers Stabilization Fund, and Andria Tupola, a former Republican member of the Hawaii House of Representatives.

In the windward side’s District 3, Alan Kekoa Texeira, a staffer for Chair Anderson, is facing off against Esther Kiaaina, executive director of the Pacific Basin Development Council, among others.

Lined up to fill Manahan’s seat representing Iwilei and Salt Lake are the councilman’s chief of staff Radiant Cordero; Jacob Aki, chief of staff for Hawaii Senate Majority Leader Kalani English; and Ryan Mandado, the founding chief academic officer of DreamHouse Ewa Beach Public Charter School.

In Menor’s District 9, which covers the area around Mililani, Espero is running against two candidates whose names will also be familiar to voters: entertainer Augie T and Earl Tsuneyoshi, a Hawaii Army National Guardsman and brother-in-law to Councilwoman Heidi Tsuneyoshi.

Ultimately, new faces don’t mean change is inevitable, said Neal Milner, a former political science professor at the University of Hawaii.

“Is there a different political culture? Are they much different from the ones they replace?” he asked. “The new politicians might think like the old ones.” 

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