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Eight years after his first campaign for Honolulu City Council, Chair Tommy Waters is running with an incumbency advantage. 

He lost his first attempt in 2014 and narrowly won the second after a special election rematch in 2019, assuming the leadership position in the nine-member council in 2020. This year, Waters faces a single opponent who is best known locally for his vocal opposition to mask mandates in schools.

The rival candidate, Kaleo Nakoa, who most recently served on the Hawaii Kai Neighborhood Board, says he filed to run because he thought Waters would run for U.S. Congress. After Waters announced his intention to stay on the council, Nakoa decided to stay in, saying he’d already committed to his candidacy.

“Maybe this is my calling to do something, or to bring up the issues that (are) going on,” he said in a recent interview.

Waters is finishing up his first term representing District 4 on the council with largely good reviews from his constituents. But his district has experienced a rise in homelessness, and he has faced criticism for less personal engagement with the community since being chosen as council chair.

Affordable Housing

Waters said the biggest issue facing Oahu is the need for homes that residents can afford to rent or buy.

The problem is prominent in his district, a relatively affluent area that extends from eastern Waikiki to Hawaii Kai. Multimillion dollar houses line the coast in Kahala; matcha soda goes for almost $10 in Kaimuki. Residents involve themselves in civic life.

A bit removed from the urban core, this area was traditionally insulated from Honolulu’s homeless population, said Lori Yamada, who grew up in nearby Palolo valley before moving to Kaimuki, where she’s chair of the neighborhood board.

Now, the number of homeless people is increasing even as they face crackdowns elsewhere on the island.

Waters recognized this during , when he referred to homelessness as his No. 1 issue. So far, things have only worsened.

A report from Partners for Care, an Oahu-based group devoted to ending homelessness, that Yamada noticed: Waters entered office in 2019, and since then, the organization’s count of East Honolulu’s homeless population has risen from 326 individuals to 575. 

Waters framed the issue as one rooted in supply, arguing that more affordable housing is needed. He said the City Council has appropriated $200 million toward creating more affordable housing, but now it’s in the hands of Mayor Rick Blangiardi’s administration. 

“The frustrating part … is that once we appropriate it, it’s up to the administration to administrate, right? And as far as I can tell, at this point, they haven’t touched any of that money,” Waters said in a recent phone interview.

Blangiardi’s office declined to comment, though the Department of Community Services did dole out back in August.

Local Concerns

In East Honolulu, residents also tend to oppose efforts to increase housing supply with large developments. “They created so they could stop and manage growth,” Waters said.

He referenced the collaboration he facilitated with Hawaii Kai’s neighborhood board in crafting the , which stipulates that any new commercial development should go in Hawaii Kai Towne Center, but that Kalama Valley Shopping Center could be the site of some new housing for young people starting out and for kupuna who are downsizing. 

Nakoa’s not convinced that building more units will be much help. 

“We don’t need more affordable housing, we need to make housing affordable,” he said. “And we need programs in there that stop these absentee owners from buying it out.” 

Both candidates agree on this last point, referring to a longstanding problem in Hawaii that outside buyers may leave houses vacant as investments. 

Waters has pitched the idea of a vacancy tax, saying that his predecessor, Trevor Ozawa, had drafted a similar bill. However, he knows that legally proving vacancy is a tough nut to crack.

Hyperlocal Engagement

Nakoa said he joined the neighborhood board in Aug. 2021 after hearing neighbors discuss the proposed senior care facility Luana Kai, which has been in the works for the past few years and , a quiet enclave of Hawaii Kai. 

Last September, the neighborhood board issued a resolution and desire to be better informed, but the project’s still in planning stages and its fate is up in the air. 

Nakoa said he decided to run for City Council when Waters was considering a run for U.S. Congress to replace U.S. Rep. Kai Kahele, who unsuccessfully ran for governor. He said he also was frustrated that Waters was not more actively involved in the debate over the Luana Kai development.

“He’s not a bad guy,” said Nakoa of Waters. “I just feel like, I mean I’ve been on the Hawaii Kai board for over a year, and he’s never been on the Zoom calls.” Nakoa’s last monthly meeting as a board member was this past July.  

Neighborhood board meeting minutes show that Waters hasn’t personally shown up as much as he used to since being elected, then named council chair. 

But in interviews, board chairs spoke highly of him regardless. 

“He responds fast to what we need,” Yamada said. The Kaimuki board chair referred to Queen Theater, a golden-age era icon on the neighborhood’s main street, Waialae Avenue, that’s fallen into dilapidation.

Its owner hasn’t cared for it, said Yamada, and the board prompted Waters to introduce a resolution last year aiming to have the city take control and restore it to its former glory.

Richard Turbin, chair of the Waialae-Kahala neighborhood board, also appreciated Waters’ hyperlocal involvement. 

A quirk in the language of what constitutes a public beach had inspired wealthy beachfront residents to plant vegetation along the sand, he said. When he invited Waters on a walk to show him the problem, they encountered a person stealing sand. 

Waters called them out, said Turbin: “He had more guts handling that person than I had.”

When it comes to neighborhood board appearances, said Turbin, Waters often sends aides. But Turbin said the aides are good liaisons. 

That’s not to say they agree with every thing the City Council has done under Waters’ stewardship. Particularly contentious was the passage of a bill prohibiting the booking of short-term rentals for fewer than 90 days – up from the current 30 days – in most areas of Hawaii’s most populous island. The new regulations take effect later this month.

Turbin thought that a 30-day minimum had been a fair compromise  – “then suddenly they increased it to 90 days out of the blue” – but overall, the board felt it was prudent to do something about the overrun of rentals that saw an influx of tourists in some residential areas, he said.

The big issue now, said Turbin, is that the council needs to improve oversight of the Department of Planning and Permitting, which is plagued by long delays and had several employees arrested last year in a bribery scandal.

Is Tommy Waters ‘Unbeatable’?

Waters’ first two campaigns for City Council were both against Trevor Ozawa, a fellow attorney who won a close race in 2014. 

Waters initially lost the 2018 election as well, but in a rare move, the state Supreme Court invalidated the result, setting the stage for a special election rematch in April 2019 that he ultimately won.

Ozawa – who had been set to become council chair after his initial victory in 2018 – chose not to run for his old seat this cycle, clearing the way for Waters and Nakoa to bypass the Aug. 13 primary and coast to the Nov. 8 general election since there were only two candidates.

Nakoa has an outsider appeal, and during a phone interview, he could be heard receiving plenty of affirming honks as his team waved campaign signs along the road. His Instagram account includes a post with former Republican gubernatorial candidate BJ Penn, and he campaigns on the idea that he’s not an entrenched politician.

“I’m the worst politician in this race, because I will speak my mind,” said Nakoa. If there’s a problematic issue in his district, he explained, he’d be upfront with his constituents rather than sugarcoat the truth.

He hasn’t sought union endorsements — “not that I don’t value their opinion, but I want to hear it from the people,” he said.

Waters, meanwhile, has strong union support, one of a few components that makes him seemingly “unbeatable,” said Colin Moore, director of the Public Policy Center at the University of Hawaii Manoa.

Because there was no primary for their race, Nakoa and Waters were not required to file campaign finance reports until Oct. 3. Nakoa raised almost $4,000 through Sept. 26 and had a little over $1,000 on hand at the end of the reporting period.

Waters raised over $300,000 by the same point in the election cycle, swelling his total cash on hand to almost $250,000.