U.S. Rep. Kai Kahele has been talking privately about running for governor since at least January, and in the months that followed some political insiders were curious, and concerned: Why wait until May 7 to formally announce he is a candidate?

Kahele’s reply will go down in Hawaii political history, no matter how the Democratic primary turns out this year. To paraphrase his response to the doubters, he essentially said: I can do it in 90 days.

If he is right, he has triangulated some sort of new statewide strategy. He must somehow overcome not only his very late entry into the race, but also a limited pool of funding to help fuel his campaign.

His leading opponent, Lt. Gov. Josh Green, has planned for this moment for years, climbing the political ladder from state House to state Senate to his current office, and pocketing campaign donations and union endorsements along the way. His campaign is carefully planned and conventional, and everyone saw him coming.

The campaign of former Hawaii first lady Vicky Cayetano was more surprising, but it unofficially kicked off last July, giving voters considerably more time to get used to the idea. The consensus in political circles is Cayetano, a successful businesswoman who is partly funding her own campaign, trails Green by a sizable margin.

Kahele bristles at this widespread speculation about his viability — or lack of it — saying it is “harmful” in itself.

Kai Kahele announces running for Hawaii Governor at Hilo Boys and Girls Club gymnasium.
U.S. Rep. Kai Kahele announced on May 7 he is running for Hawaii governor. Kahele said he and his supporters are “not worried in the slightest” about the barriers his campaign faces. Cory Lum/Civil Beat/2022

“The rhetoric around our campaign referencing the ‘uphill’ battle we are facing — whether due to entering later than the other candidates or the challenge of raising enough money — embodies the core problem in Hawaii’s politics,” Kahele said in a written statement.

“These comments insinuate that a candidate must have a war chest of money and a decades-long political career to be viable. This is harmful,” he wrote. “I have neither of those things and yet, over the last two weeks, our campaign has seen enormous support from voters who are tired of the status quo and are appalled at the outside mainland money attempting to influence the race for governor.”

Kahele is right that money isn’t everything, of course. Gov. David Ige shocked many Hawaii political insiders in 2014 with his upset of former Gov. Neil Abercrombie, and Ige had far less campaign money to spend than Abercrombie.

But Ige also allowed himself more time to make his pitch to the voters. Ige publicly announced he was a candidate for governor on July 9, 2013, which was a full 13 months before the 2014 primary election.

This year, primary voters will begin receiving their mail-in ballots on July 26, according to the state Office of Elections, which means voting actually begins in about 60 days. Primary election day is Aug. 13, so time is running out.

And there are other important factors in the mix. Chuck Freedman, who managed communications for former Gov. John Waihee’s campaign in 1986, said this is an unusual gubernatorial race because Green as lieutenant governor “built portfolio” by using his credentials as a physician to take center stage during the pandemic.

“He played a role in both making policy and criticizing it at the same time, but he certainly made a name for himself as lieutenant governor, and really that’s never happened before in Hawaii,” he said. “It gives him a big advantage.”

Kahele is a Hawaiian, a war veteran, a lieutenant colonel in the Hawaii Air National Guard and a Hawaiian Airlines pilot, which can all be political assets. Freedman said he also has an “enormous personality” and an energy that appeals to some voters.

“But he is running against the clock, both in establishing his name for people who don’t really know him, and in raising money, which for the governor’s race is no small thing,” Freedman said.

“I think it’s pretty darn late, and yet at the same time, if he has a real clear strategy, with a ground game that’s already set up and ready to go … there’s enough time for a meteoric campaign, but he has to really be looking at the clock and looking at a chart with all of the critical dates on it. For him, hopefully he’s set up to do that.”

Freedman is retired and not involved in any of the campaigns for governor, but said he donated $100 each to Green and former Mayor Kirk Caldwell, who has since dropped out of the race.

Lt Governor Josh Green discusses COVID-19 testing with partners before passengers are allowed to arrive in Hawaii from October 15, 2020
Lt. Gov. Josh Green discusses Covid-19 testing protocols in the fall of 2020. Green “built portfolio” by playing a very public role in the pandemic, and was helped in that effort by his credentials as a physician. Cory Lum/Civil Beat/2020

Given Kahele’s limited prospects for raising money, he was wise to try to reframe his lack of campaign cash into a narrative about the harmful influence of money in Hawaii politics, said Robert Perkinson, an associate professor of American Studies at the University of Hawaii Manoa.

Many of the big-money donors on the Hawaii political scene have already backed Green, which means criticizing the influence of “wealthy donors” costs Kahele little.

Likewise, many of the largest unions have endorsed Green, so Kahele’s suggestion that Hawaii “could” ban political contributions from unions fits comfortably with his political situation.

Campaigning against the influence of big money in politics “is the smartest move he could make on the chessboard he has, with so few pieces,” Perkinson said. He noted the Bernie Sanders campaign in 2016 raised an enormous sum nationally from small donors, but that is far more difficult to do in little Hawaii.

Perkinson said Kahele starts off “in a pretty deep hole,” mostly because of his late start. “I’m not counting him out, but I do think he’s starting well after the gun fired in the race, and that means even if you run faster, the odds are still against you.”

Another problem for Kahele is that he is generally seen as a left-leaning, progressive sort of Democrat, and Green has a similar political persona, Perkinson said. As a businessperson, Cayetano generally has an image that puts her more toward the political center.

If Kahele were running against a conservative candidate, he could try to mobilize unions, the young and other interest groups, but that may not be possible in this race, Perkinson said. In the end, it may be challenging for Kahele to distinguish himself from Green on policy questions.

As a sitting congressman representing rural Oahu and the neighbor islands, Kahele is probably better known than Ige was at the start of Ige’s first campaign for governor, particularly on the neighbor islands.

But Ige got a close look from many Democratic voters that year because he ran against the often controversial, shoot-from-the-hip incumbent Neil Abercrombie. Conventional political wisdom holds that Abercrombie lost that 2014 campaign as much as Ige won it.

Gov. Neil Abercrombie speaks to David Ige’s supporters soon after Abercrombie conceded the election to Ige in 2014. Ige’s win came as a shock to some insiders, but Ige campaigned for 13 months before the primary election. Cory Lum/Civil Beat/2014

Green is far more careful about the things he says publicly than Abercrombie was, but personality will still be part of the mix. A number of Capitol insiders and other community leaders say privately they dislike Green personally, and people who have worked closely with him report he can be snappish and arrogant.

Green doesn’t deny that. When asked about that reputation, he replied in an interview that “I fight hard for things I believe in, so sometimes that rubs career political people — who expect you to just go along — the wrong way.”

Of Kahele’s entry into the race, Green said that “I wish him well. We did poll to see how each of our competitors would do, and those polls have been made public … They show that people have been very supportive and I’m very honored to have the support of a lot of people in Hawaii.”

That internal poll by the Green camp in late March showed Green with a large lead in a primary race that included Green, Kahele, Cayetano and Caldwell.

Now that Caldwell has quit the race, the dynamic of a three-way Democratic primary between Green, Kahele and Cayetano may turn out to be important. Last weekend a political action committee funded in part by donors to Cayetano’s campaign fielded a political ad that questioned Green’s credentials as a physician, pointing out that he is not board certified.

Green does not need to be board certified to practice medicine in Hawaii, and some of his union supporters denounced the ad as a “smear campaign.” But it raised the possibility that cross-fire criticism from both Kahele and Cayetano supporters could chip away at Green’s image and political standing over time.

Observers who believe a primary upset is still possible this year sometimes point to 1986, when a poll by The Honolulu Advertiser had John Waihee trailing wealthy broadcast executive Cec Heftel by 36 percentage points just six weeks before the primary election. That poll had Heftel at 54%, while Waihee had 18% and Patsy Mink had 10%.

Heftel had been elected to five terms in the U.S. House representing Hawaii, and was also the best-funded candidate in the race, outspending Waihee and Mink by more than two-to-one. He resigned from office in July, 1986 to return to Hawaii to campaign.

As it turned out, Hawaii voters decided Heftel looked better “from far away,” Freedman said. Waihee was lieutenant governor at the time, and after the candidates debated “people started to believe that Waihee had more resonance with them than Heftel did,” Freedman recalled.

Waihee finally won on primary election day with 45% of the vote, while Heftel had 36%, and Mink had 16%. Heftel blamed his loss on an anonymous “smear campaign.”

Hawaii’s former First Lady Vicky Cayetano during News conference at Hawai‘i State Capitol grounds on Monday August 30, 2021. Ronen Zilberman Civil Beat.
Former Hawaii First Lady Vicky Cayetano at a news conference at Hawaii Capitol grounds on Aug. 30, with former Gov. Ben Cayetano to her right. “You never know what will happen,” she said. Ronen Zilberman/Civil Beat/2021

Freedman said televised debates may turn out to be the pivot points in the campaign this year. “I can tell you that debates really change things when you get a side-by-side look at the candidates,” he said. “If Kai is really ready, he can change the energy somewhat.”

Viewers will be influenced by the candidates’ demeanor as well as signs they understand important pocketbook issues, can handle pressure and can connect with the public on some meaningful level, he said.

“Clearly, Kai is going to want to debate,” Freedman said. “I think that people who, generally speaking, are underdogs, which would be Vicky and Kai, who both I think are good articulators of their message, will want to see debates, and that could make a difference.

“It’s not just the debates but how the debates are covered, and what Mrs. Oshiro tells Mrs. Fukunaga over the fence.”

Kahele insisted in a written statement that “our campaign is not worried — in the slightest — about these alleged barriers to winning.”

“Rather, we are inspired by the momentum our campaign is generating across Hawai’i. We remain confident that our campaign resonates with Hawai’i’s working families and those struggling every day to live and thrive here at home in a way that has been missing from Hawai’i for decades,” he wrote.

Cayetano for her part declined to handicap Kahele’s chances, saying only that “You never know what will happen in a political race, as seen from past outcomes. It is a cliché, but you just never know until the election is over.”

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