Former Mayor Kirk Caldwell's gubernatorial campaign faces early fundraising challenge

Aug. 4—Former Mayor Kirk Caldwell's gubernatorial hopes suffered a serious blow when he struggled to raise just $9, 760 in campaign contributions over the past six months.

"People don't think he can win, " said Colin Moore, director of the University of Hawaii's Public Policy Center. "I think it's that simple."

The Democratic Primary for governor is still a year away, but Moore said Caldwell's latest fundraising numbers show that his gubernatorial ambitious are in political peril.

Only six individuals and one company donated to his campaign since February, according to the latest financial disclosure information that Caldwell's campaign reported Monday night to the Campaign Spending Commission.

By comparison, Lt. Gov. Josh Green raised $424, 212 during the same period through more than 230 donations, including well-known names in the community and health officials, who sometimes donated more than once.

If Caldwell fails to make it out of the primary, he would join a list of Honolulu mayors who could not win the governorship, including Mufi Hannemann and the late Frank Fasi. Former Maui Mayor Linda Lingle did become governor after branding herself as a moderate Republican neighbor island outsider and served two terms starting in 2002.

Hannemann served as mayor from 2005 to 2010 and remains chief executive officer and president of the Hawaii Lodging &Tourism Association. He ran for governor in 2010, Congress in 2012 and governor in 2014.

Fasi, who died in 2010, won election to the mayor's office six times and lost five times but failed to win the gubernatorial race in each of his four attempts.

Big-city mayors around the country get both credit and blame, sometimes for issues they're not even responsible for, said political analyst Neal Milner.

Locally, both Hannemann and Caldwell are blamed for the city's troubled rail project, which faces a $3 billion shortfall and no plan to complete the system to Ala Moana Center.

"Caldwell has rail hanging over him, for sure, " Milner said.

Caldwell's campaign Tuesday issued a statement to the Honolulu Star-Advertiser that said, "Kirk thought it was important to start his campaign for governor by connecting first with the community leaders on Oahu and all the neighbor islands, not on raising money. That was his major focus in the first part of the year. He held his first major fundraiser, via Zoom, at the end of July. Kirk looks forward to a vigorous campaign, and to debating all of the many issues facing the entire state."

During a July appearance on the Star-Advertiser's Spotlight Hawaii livestream show, Caldwell was asked about his political future after serving as state House majority leader and two terms as mayor.

"I liked elected office, " Caldwell told Spotlight Hawaii. "It's in my blood and I'm not ready to retire. I want to run for higher office. As you know, I've had some fundraisers running for governor, and I'm working very hard reaching out to the community, to the people of Hawaii, to get their support in a race for governor. It's just begun."

Since leaving the mayor's office because of term limits, Caldwell said he has been traveling to the neighbor islands "talking story " and "basically listening more than talking and feeling their concerns and their joy."

Unlike other potential gubernatorial candidates, Caldwell told Spotlight Hawaii that he is the only one who has had to make tough decisions as an elected official.

And that may be part of the reason for Caldwell's low fundraising numbers so far.

"That's why no (Honolulu ) mayor has ever become governor, " Moore said. "You make a lot of hard decisions, you make a lot of enemies compared to being Lt. Gov. Green. Being L.G., you're sort of in the sweet spot. That's why it's always been a great position. You get a lot of publicity without a lot of responsibility. The COVID crisis was perfect for someone like Josh Green, who's a physician. It's a very different situation than being mayor. You can pick your battles, but you're not really responsible for anything."

Green, a Big Island emergency room physician, has been a leading voice during the COVID-19 pandemic, sometimes offering different perspectives from Gov. David Ige.

Former Hawaii first lady Vicky Cayetano told the Star-Advertiser last month that she is considering a gubernatorial run, but did not file a campaign spending report by Monday night's deadline.

Even if Cayetano mounts a campaign, Moore said that she would not represent a challenge to Green.

"She's a very credible candidate and a candidate to take seriously, " Moore said. "In a Democratic primary a wealthy businesswoman like Vicky Cayetano will do OK, but she won't get more than 25 % or 30 % of the vote. It's not going to be enough."

Caldwell's fundraising report is certain to get attention and raise questions about his chances that could further jeopardize his campaign, Milner said.

"It certainly suggests to me that Mayor Caldwell has a much rougher road, " Milner said. "You would think because he's raised big money in the past that he had a pretty strong network of people who would give money."

Moore was more blunt.

He believes Caldwell's latest fundraising figures show a campaign in early trouble.

"One of the mayor's advantages has been that he's always been able to raise money, " Moore said. "He's from finance. He has money. In the past that was always something Kirk Caldwell could deliver : money. Being mayor of the City and County of Honolulu, you have a lot of baggage. Donors like to invest in a candidate they think can win."