Former Mayor Kirk Caldwell sees neighbor island path to governorship

Former Mayor Kirk Caldwell calls himself “the underdog” in the three-way race for governor in the August Democratic primary but sees a path to victory through the neighbor islands, despite his unpopularity after serving two terms and eight years at Honolulu Hale.

Caldwell is proud to discuss his record, saying he was willing to make “tough decisions” that were not always popular, including embracing new ways to address homelessness on Oahu that had never been tried in the islands; his backing for the city’s troubled rail project that he inherited and continues to support; and his early response to COVID-19 as the pandemic started strangling Honolulu’s economy in March 2020.

Asked if he was unfairly blamed for homelessness and rail two years ago when term limits prevented him from running again, Caldwell told the Honolulu Star-Advertiser:

“I stood up and fought for difficult issues and didn’t back away. I never ran from it (rail). I became the face of rail … and got my butt kicked by the Legislature” for twice seeking state funding.

“I was the mayor and these things happened while I was mayor,” Caldwell said. “You need a governor who’s willing to stand up and make the difficult decisions.”

Caldwell is running against Lt. Gov. Josh Green and Vicky Cayetano, a business entrepreneur and former first lady.

But Caldwell has provided some of the most specific details on some of the most critical issues facing Oahu and the entire state through a series of ads in the Star- Advertiser and neighbor island newspapers.

The first appeared under the headline: “Why I’m running for Governor Even if some people don’t think I can win.”

It touched on Caldwell’s ideas to build more affordable housing; do more to reduce homelessness; help families by eliminating the general excise tax on groceries, medications and diapers; finish rail construction; respond to climate change; and do more to get Native Hawaiians on their ancestral lands, among other topics.

In seven subsequent ads, Caldwell goes into even more detail. The latest ad carries the headline: “The most important issue is character.”

The strategy was aimed at “high information voters” who read newspapers, Caldwell said.

Instead of a quick television commercial with simple messaging, Caldwell said he wants “to write in detail what I’m going to do in detail.”

“I’ve tried to call it as I see it,” Caldwell said. “Our goal was to draw more attention to the issues that I think the state needs to address now, right now.”

Caldwell is proud of his roots: Born in Waipahu and raised in Hilo, where his father, Paul Caldwell, was the only obstetrician treating plantation and sugar mill families for 30 years.

“He delivered thousands and thousands of babies,” Caldwell said.

Caldwell’s upbringing gives him entry to rural and neighbor island voters because he sympathizes with their challenges, he said.

“Being born in Waipahu and raised in Hilo — people from rural communities know what that means,” he said. “I didn’t grow up in urban Honolulu or spend most of my life on Oahu.”

Even while campaigning in remote areas such as Molokai, Caldwell said, his shock of white hair and voice make him recognizable even while wearing a mask and hat.

He believes he can pull off a win by shoring up prior support from Oahu voters and attracting new neighbor island voters in places including Hilo, Wailuku, Kahului and Lihue.

Caldwell said he is sometimes asked on the campaign trail about his former Managing Director Roy Amemiya, former Corporation Counsel Donna Leong and former Honolulu Police Commission Chair Max Sword. The three have pleaded not guilty to federal charges surrounding the $250,000 retirement settlement for former Honolulu police Chief Louis Kealoha, who was later convicted of federal crimes and is now in prison.

Caldwell thinks Amemiya, Leong and Sword will be exonerated.

“I’m not running from them,” he said. “I’m not distancing myself. They come from families where their reputations are important. I believe they’re innocent and will be proven innocent.”

No Honolulu mayor has ever been elected governor and Colin Moore — director of the University of Hawaii’s Public Policy Center — wonders why Caldwell, a lawyer, thinks he can be the first.

“I think a lot of people have asked the same question,” Moore said. “The polling is abysmal because he’s connected to unpopular projects.”

Former Mayor Frank Fasi — Honolulu’s longest- serving mayor — held office for 22 years in a 26-year span but died in 2010 at the age of 89 having never been elected governor.

“If Frank Fasi couldn’t do it, who can?” Moore asked.

As for Caldwell, Moore said, “His ads themselves say, ‘Many people don’t think I can win.’ The only thing I can come up with is that he sees it as a civic duty. He sees his experience and accomplishments as mayor as the right skill set to run the state. He has the resources to run a strong campaign and Kirk Caldwell has come from behind before.”

Moore cited the 2012 mayoral race, in which no candidate won a simple majority of votes in the first ballots that would have led to a direct victory. In the first round, Caldwell received some 30,000 fewer votes than former Gov. Ben Caye­tano. But Caldwell pulled out the win in the second round by nearly 23,000 votes.

In his 2016 mayoral race against former U.S. Rep. Charles Djou, Caldwell was behind in the polls but ended up winning by a margin of 12,231 votes.

Moore said as mayor, Caldwell was “a technocrat who … could probably identify the number of fire hydrants in Manoa Valley.”

In one ad, in fact, Caldwell lists repaving “2,300 lane miles of roadways” as one of his accomplishments.

The ads offer refreshing candor, Moore said.

“He’s confronted his liabilities pretty directly,” Moore said. “He’s talked about rail. I think he hopes that voters will decide that Vicky Caye­tano isn’t enough of a Democrat for them and something will happen to the Green campaign.”

John Hart, a Hawaii Pacific University communications professor, said Caldwell is playing the political hand he was dealt by confronting his challenges and leaning on his policy strengths.

“We have some real problems, but we don’t have a lot of serious discussions about policy,” Hart said. “And presenting yourself as an underdog is probably a good tactic in this race.”

Since he’s been out of office, Caldwell spends his time traveling across the islands to campaign when he’s not trolling, shore casting and spearfishing for ulua and papio, especially around South Point on the Big Island.

But mostly he thinks of the work his administration did for the people of Oahu — and what he could do for the state as governor.

“I miss my old job,” he said. “I’m in this to win.”