The Odds Are Stacked Against Caldwell

There is an obvious reason why no mayor of Honolulu ever becomes governor of Hawaii.

Every voter on Oahu (where the most votes are) remembers if the mayor did not fix the big pothole on his or her street, even after several calls to City Hall.

Every Oahu voter remembers if the grass and the restrooms in his or her neighborhood park went into decline.

And then there is familiarity. The mayor deals with Neighborhood Boards and tries to tamp down neighborhood squabbles over beach access, unleashed dogs and district homelessness. City voters say “no way I gonna vote for for him [her]. He [she] is pilau.”

The late Frank Fasi kept a grip on the mayor’s office but was rejected for governor. He gave us great bus service but voters suspected he had taken Kukui Plaza kickbacks and was saved from prison only because developer Hal Hansen took an oath of silence and went to prison without saying to whom he gave the kickback money.

Linda Lingle was elected governor but she was Maui County’s mayor. We on Oahu knew little about what she’d done or not done. Besides, former Gov. John Waihee, a Democrat, had earlier been booed at the Waikiki Shell for blowing our rainy day fund and we had another Democrat governor, Ben Cayetano.  Lingle was a Republican. Voters were ready for a change.


Mayor Mufi Hannemann went for governor in 2010 but lost to Neil Abercrombie in the primary.  Was smashed by Tulsi Gabbard in his second go (after also  losing to Abercrombie) for Congress. People had started souring on the train project, Chinatown homeless, and some even said he was too tall!

I mention all this because I’m curious why Kirk Caldwell, Honolulu’s mayor and  announced governor candidate for 2022, would try to break the curse.

It’s not as if he’s wildly popular. He had to be community-wide-challenged before he’d go back on his Ala Moana Park playground project, his Waimanalo Park (Sherwood Forest) ballfields and parking lot project went south after image-damaging protests, and he remains haunted by the train costs and damage to merchants along Dillingham Boulevard. Now the virus damage to local business and our financial situation.

He would have to overcome the head-start of Lt. Gov. Josh Green in a race that sometimes sometimes has given our lieutenant governors  a leg up in  elections. But to for everyone. Those who did not rise to #1 are Jimmy Kealoha, Tom Gill, William Richardson, Nelson Doi, Jean King, Duke Aiona and Mazie Hirono.

In a reverse scenario of the usual movement, former Gov. Ben Cayetano ran for Honolulu mayor in 2012 after he was termed out of the State Capitol. He lost big time.

If there was ever a mayor who might have been a popularly-elected governor it was Neal Blaisdell, a Republican who played footsie with Hawaii’s rising Democratic leadership after statehood.

“Rusty” Blaisdell was extraordinarily popular from the start to his finish in politics in 1969. He beat out Frank Fasi in 1955. He built the Wilson Tunnel and the International Center at Ward and Kapiolani which now bears his name — Fasi promoted that name change.

But he died in 1975 without even thinking about running for governor. He’d had health problems for much of his late life, including pneumonia which sidelined him early in his political aspirations.

There’s a reasonable chance that Colleen Hanabusa could win this years mayor’s race. She has a history here as State Senate president and congresswoman.  If she were to win, would she dump out two years into City Hall to run for governor? That wouldn’t sit well with most voters. But …

“No,” she told me. “This [the mayor job] would be it for me.”

I should have replied: “Historically, a very wise decision.”



Published by Bob Jones

Journalist since age 19. St. Petersburg Times, Noticias y Viajes in Madrid, Overseas Weekly in Frankfurt and Paris, the Louisville Courier- Journal, the Honolulu Advertiser, KGMB-TV, NBC News foreign correspondent in Africa and Southeast Asia, and MidWeek columnist. LL.B LaSalle University Law. 3 years in the U.S. Air Force. Covered: Biafran War in Nigeria (1968) Vietnam War (1969-73), Iraq in 1991. George Foster Peabody Award for distinguished journalism for reporting in China. 2 Emmys for documentaries. Married to journalist Denby Fawcett; one daughter. Brett Jones, foreign service officer, State Department.

11 replies on “The Odds Are Stacked Against Caldwell”

  1. Correction: Linda Lingle did not run against Gov. John Waihee, as you implied. In fact, Lingle lost her first run for governor in 1998. She benefited from the defeat as the voters got to know her better. In her second try, Lingle beat Lt. Gov Mazie Hirono in 2002 and was re-elected four years later by beating a woefully underfunded Randy Iwase in 2006. Hirono would avenge her loss to Lingle by defeating her in the race for US Senate. As for Caldwell running for governor, I would not sell him short.

      1. A Hawai’i gubernatorial candidate cannot win the general election without winning the neighbor islands. First, a Democratic candidate cannot win all of Honolulu/O’ahu with its pockets of GOP Precincts. Second, the neighbor islands vote pretty lopsided for Dems. Caldwell lived on the Big Island but went the HPA, just like Ed Case. They both have no deep roots on the neighbor islands. They can talk the slang but look uncomfortable in rubbah slippahs eating beef stew or chili and rice.

    1. Wasn’t Lingle defeated in 1998 in part because her well-funded opponent received LOTS of illegal campaign contributions that were not discovered until long after the election?

        1. Additional information and concise summary:
          “The commission has levied fines against 75 companies for making illegal contributions to Democrats, such as Harris, former governor Ben Cayetano, former mayor James Apana of Maui County, and former lieutenant governor Mazie Hirono. As many as 40 more companies are being investigated.”

  2. Oh the way you think voters turn out. Ask the power brokers all Dems and not ever loosing except for Lingle. The unions could not stop her. The positives of a candidate were her and women pushing her over the top in ‘98 primary. Over 100,000 women did it. Best list of supporters ever.
    There is a dark horse but would Harry Kim ever run for Governor? His positives are two to one. Even Ige let him run the show.
    If the unions have to chose the candidate they help the one who will helps them.
    Not pot holes or traffic or Rail. Contractors and unions are a one big group now. Ask Pacific Resources who they like.

    1. Republicans should ask themselves why the Hawaii GOP is dysfunctional and why today it is considered an endangered political species. I suggest its demise began in 1988 when the GOP was taken over by the Religious Right and nominated evangelist Pat Robertson to run as its Favorite Son in the 1988 presidential election. The takeover caused an exodus of liberal and moderate republicans to the Democratic Party from which the GOP has never recovered. I served with some fine and skillful republicans. Sadly, today they are as rare as the Nene Goose.

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