Kirk Caldwell handed the keys to the third-floor corner office at Honolulu Hale to incoming Mayor Rick Blangiardi on Jan. 2 — with only a few regrets but not just a little reluctance.

And while Caldwell has made no secret that he is exploring a 2022 run for governor, the truth is he’d really rather have continued being your mayor another four years.

That stems partly from his wish to see rail and other large infrastructure projects completed, he said. But, in broader terms, he said, “Being mayor is the best public-service job I think you could have, because you can make a difference in people’s lives every single day in small ways and very, very, large ones.”

He pointed out that three of the 15 people to hold the title of Honolulu mayor left, and then returned for subsequent terms.

Caldwell, 68, said he wants his enduring legacies to be that he dreamed big and, to quote a phrase he’s used a lot over eight years, “always ran toward danger, not away from it.”

“From my first day I’ve been out in the trenches, I’ve been available to the public, I’ve had more press conferences than probably anybody in the history of the City and County of Honolulu, as mayor,” he said.

“I’ve not been afraid to answer every question that’s been asked. I make myself available and I go before the people,” Caldwell said in two far-ranging interviews with the Honolulu Star-Advertiser during the final weeks of his administration.

Count among the hot-potato issues Caldwell had to deal with the ever-controversial, now $11 billion rail project, his carrot- and-stick “compassionate disruption” approach to tackling homelessness and a climate crisis policy that included a plastics ban that’s riled the restaurant industry.

“But these are the kinds of thing you’re going to have to do if you’re going to dream big,” Caldwell said. “And big dreams, big projects generate controversy, and controversy is never popular.”

Too often, other politicians are reluctant to take chances and advocate for change, he said. “By playing it safe, they don’t get criticized and they can retire — no problems. I, on the other hand, seem to be in a controversy every other day. Not because I’m seeking them out, but because I’m holding the line and fighting for those big dreams that need to be done.”

Most recently, Caldwell placed a big target on his back by imposing a strict, pandemic-related tiered reopening policy that’s drawn the ire of many in the business community.

During his last two years, in particular, Caldwell’s popularity ratings dropped dramatically, and there appeared to be a growing sentiment that he wasn’t listening to the public. Projects including renovations to Ala Moana Regional Park, Neal Blaisdell Center and Sherwood’s in Waimanalo were cited as some of the examples.

After first refusing to yield on those three very different projects, Caldwell capitulated on each. The highly divisive plan for an inclusive playground at Ala Moana was redirected to Kakaako, Blaisdell will for now undergo a much smaller scale of improvement and the Waimanalo park improvements were halted altogether.

All three projects went through public vetting processes, although Caldwell acknowledged that more meetings could have been held in most instances.

Of the three projects, Caldwell said he’s most concerned about the future of Blaisdell, which was supposed to undergo an overhaul that would have cost nearly $800 million.

First opened in 1964, the former Honolulu International Center has never undergone extensive renovations. “It’s going to need to be rebuilt, and at whatever time, it’s going to cost more,” he said.

Caldwell said that at Ala Moana, plans for the inclusive playground and dog park may have been scrapped, but the city’s largest recreational area still received a major face-lift, including repaving of parking at Magic Island, new walking paths and a sand volleyball court.

“People don’t like change,” he said.

Deputy Managing Director Georgette Deemer said, “I think a lot of people feel they were not listened to because the mayor did not do what they wanted him to do. That’s not a fair assessment of the situation. He did listen, but at the end of the day, it’s his job to do what he feels is the right thing to do for everybody, not just a handful of people.”

But he also compromised at Ala Moana, Deemer said, removing plans for more makai parking. He also took out a proposal for an expanded promenade that had been pushed by planners.

Caldwell has had more success with his Kakou for the Parks program, which wound up renovating 119 comfort stations, resurfaced 393 play courts, refurbished playground equipment at 119 parks and put in new play apparatus at 21 others.

Another source of controversy involving city government was the federal corruption case that led to the convictions of former Honolulu Police Chief Louis Kealoha, wife and ex-Deputy Prosecutor Katherine Kealoha and several other police officers.

The chief is hired and fired by the Police Commission, whose members are appointed by the mayor and approved by the Council. As a result, Caldwell has been at the edge of the controversy. Critics have argued that he could have placed more pressure on the commission or spoken more critically against the police chief earlier on in the investigation.

He said it’s an issue that he’s played over in his mind many times. Ultimately, he said, he’s concluded, “How do you know something you don’t know until you know it?”

Caldwell insisted that all he could do was appoint new commissioners as vacancies opened up, and noted that he appointed independent and reform-minded people including attorney Loretta Sheehan and former Supreme Court Justice Steven Levinson to the panel.

Not surprisingly, the other thing that’s kept Caldwell up many nights is the problem-plagued rail project. When he entered office in January 2013, he promised to “build rail better.” The estimated cost at the time was about $5 billion with an estimated completion date of January 2020. Today the estimated cost is $12 billion with a completion date between 2027 and 2030.

Relations between the Caldwell administration and the Honolulu Authority for Rapid Transportation began to sour about halfway into the mayor’s first term. Caldwell said that he initially believed what details HART officials would provide him. “But within my first term I recognized what they were saying was not correct,” he said.

Looking back, he said he would have supported eliminating the semi-autonomous HART in favor of a rapid transit division within the Department of Transportation Services, an agency whose director reports to the mayor.

As things now stand, “I have the responsibility but none of the authority,” Caldwell said.

On housing and homelessness issues, Caldwell said he’s urged Blangiardi to continue with his “compassionate disruption” policy using “sit-lie” and “stored property” laws that make it easier for either the Honolulu Police Department or other city agencies to remove both those who call the streets their home and their belongings.

The American Civil Liberties Union’s Hawaii branch and others have raised strong objections to imposing the laws, as well as corona­virus-related citations, noting that it’s especially objectionable to roust people from city streets, sidewalks and parks in the midst of a pandemic. The critics note that the number of Oahu homeless has actually gone up during Caldwell’s eight years.

But Caldwell said detractors tend to forget the “compassionate” part of the compassionate-disruption policy and that under his administration the Hale Mauliola Navigation Center at Sand Island, the Kahauiki Village partnership with the state and business leaders, the Punawai Rest Stop in Iwilei and the Homeless Outreach and Navigation for Unsheltered Persons (HONU) initiative all began. The city’s Housing First initiative has provided vouchers for 625 families and individuals, including homeless veterans.

Caldwell said he’s also pleased that he did not have to raise the standard residential property tax rate, which remained at $3.50 per $1,000 of assessed value through his two terms. That claim comes with an asterisk, however, as he did raise rates for the hotel and resort class, and create the new and controversial Residential A tax class, which imposes a significantly higher tax rate on homes valued at $1 million or more and doesn’t have homeowner exemptions.

A long-running debate over enforcement and management of residential vacation rentals was resolved through legislation that cracks down on the advertising of illegal rentals. The ordinance allows for no unhosted transient vacation units, but several thousand hosted bed-and-breakfast establishments, although a permitting processing has not yet been established by the Department of Planning and Permitting. Major advertising platforms Airnbnb and Expedia agreed to help with the enforcement of the laws.

As for what’s next for Caldwell, he said he intends to spend time with his brother fishing at South Point on Hawaii island, visit some of the other islands with wife Donna Tanoue, and work on two books — one on people who’ve displayed courage during the pandemic. He also intends to ask the University of Hawaii Richardson School of Law whether they’d like him to teach a class there.

“And I will be looking to build a campaign infrastructure to run for governor,” Caldwell said. “As long as my health and energy holds.”

As for the idea of one day making another run for mayor, Caldwell said he is rooting for Blangiardi to be successful and has met with him several times since his election in November.