FIRST IN A SERIES

It was two years ago when Kirk Caldwell found himself a politician without a campaign.

Having been disqualified from running for City Council — a blunder caused by timing and a decision to challenge his own candidacy — he was forced to sit out the 2008 campaign season.

But he learned something.

First and foremost was to not leave things until the last minute, as he did with his filing.

He also learned something about himself: "that I loved public service, that I missed not serving," he says. "There was a period of time when I was back practicing law full time. And while I loved the intellectual challenge of practicing law, I missed not serving the public.

"For me, going home every night and knowing that I helped people in my community was something that I missed tremendously."

And he vowed to get back in the game.

"You learn a lot about people by the way they manage hardship," says Georgette Deemer, communications director for the House majority caucus, who worked closely with Caldwell during his two years as majority leader. "He turned it into a positive. It made him focus on the fact that public service was really important to him, and I’m not surprised at all that he would want to continue contributing to the community in some way.

"At that point he didn’t know what it was going to be, but it’s not surprising that this is the direction he would go in."

Today, Caldwell finds himself as the city’s acting mayor and one of four major candidates seeking the job permanently in the special election to fill the final two years of the term vacated by Mufi Hannemann, who resigned in July to run for governor.

It was Hannemann who rescued Caldwell from his political purgatory.

After winning re-election in 2008, the mayor was putting his Cabinet together for his second term and phoned Caldwell to see whether he was interested in being managing director, the city’s No. 2 executive.

"I was interested, obviously, because here was a way to get back in and serve and work on the two issues I was passionate about: rail and work-force housing," Caldwell says. "We talked and I jumped at the offer."

For the past 18 months he has been on the job as Hannemann’s second-in-command, working on the administration’s $1.82 billion budget and managing a work force of about 10,000 employees.

He has been the administration’s mouthpiece in City Council meetings, and since taking over July 20 as acting mayor, he has been a visible presence in and out of Honolulu Hale with frequent news conferences and recognition ceremonies.

Among his first announcements was an initiative to provide bus service to people in homeless shelters and transitional housing in West Oahu to help connect them to job opportunities and the community in Kapolei. More recently he rushed out proposed legislation to help provide tax credits for a "gap group" of about 250 people who saw their property tax rates soar after the city reclassified their properties from residential to commercial/ industrial.

Critics, mostly his opponents, continue to point out that roads need fixing and parks need long-overdue repair and maintenance. The issue of homelessness continues to weigh on the city as well.

The next mayor stands to inherit the task of implementing — or killing — the city’s planned $5.5 billion rail transit system, as well as a settlement with the U.S. Environmental Protection Agency to improve the city’s sewage collection and waste-water treatment systems.

Caldwell welcomes the challenges. He promises a collaborative leadership style to tackle the problems facing the city.

"Mine is one of letting everyone have a voice, hearing what they think, and once everyone has weighed in, we make a decision and we implement, and I think it is a style of working together," he says.

"You can fill in a pothole. You can improve a bus stop. You can get rid of graffiti. You can deal with the homeless issue," he says. "The thing is, you can make a difference immediately to improve people’s lives. That’s why I accepted the offer to be the managing director. That’s why I think it’s important. That’s why I’m running now for mayor."

Caldwell plans to move full steam ahead on the rail project — one of the key issues that prompted his planned jump to city government two years ago. Another was trying to develop affordable housing in urban centers to help people live closer to where they work.

While working on the majority legislative package, Caldwell says he kept stumbling over how he could advance those issues from a state perspective.

That’s when Ann Kobayashi resigned her City Council seat to run for mayor.

"I thought: There’s a perfect opportunity. I’ll run for the Council, and I’ll do it from that side," he says.

But Kobayashi resigned on the day of the candidate filing deadline for office.

"By the time I could confirm there was an opening, I had about four hours," Caldwell says.

Caldwell furiously tried to get the required 15 signatures for his filing papers, and he submitted his paperwork with one minute to spare before the 4:30 p.m. deadline. But in the last-minute scramble, his application came up one signature short, and Caldwell wound up getting the signature of a Manoa resident working in the City Clerk’s office to get the required 15.

Questions were raised, and opponents threatened to contest his candidacy but Caldwell ultimately decided to settle the matter by filing his own challenge.

"Here I am, a trained lawyer, a professional lawyer practiced 30 years in litigation, yet I said I will bring this challenge and live with whatever the result is," Caldwell says. "I said I’m not going to play lawyer and appeal it. I’ll accept it, respect it and move on. And that’s what I did."

The challenge did not go in his favor, and Caldwell was disqualified from the race for failing to withdraw from his House race prior to filing for the Council vacancy.

"I think, personally, he was deeply affected by it because he truly and sincerely enjoys the privilege of public service," said Rep. Marcus Oshiro, who preceded Caldwell as majority leader in the House. "He’s one of those folks that get up each morning ready to face the challenges to work toward a better future for all of us."

But it’s not all work all the time for Caldwell, particularly if he finds himself at "Pops" in Waikiki with his surfboard on an early Sunday morning.

The peace and tranquility he feels from surfing momentarily take him away from the pressures of the mayor’s office and the campaign, until someone recognizes him and wants to talk politics.

"I try to change the subject — quickly," he says.

He would rather talk about catching the perfect wave.

"A nice, long white going toward Diamond Head — and you can go a long time on some of those waves at Pops," he says. "You see Diamond Head. You see Waikiki. I feel alive. I feel connected.

"That kind of wave, no matter how I go into the water, I come out healed."