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When Mayor Kirk Caldwell was running for mayor in 2012, he promised to help the homeless, “build rail better” and be a dependable leader for Honolulu.��

Eight years later, as the mayor eyes a run for governor, the island is in much the same place as it was when Caldwell took office, political observers say.��

Some areas have gotten better. There are fewer potholes and sewage spills, for instance. Honolulu also gained bike lanes and finally took action on illegal short-term rentals, which neighbors had complained about for years.��

But Caldwell’s leadership did not cause the island to make a quantum leap. Honolulu has not been transformed by his efforts.����

And some areas have gotten much worse – most notably two that Caldwell promised to improve: the rail project and homelessness.��

“He tends to try to do so much at the same time instead of being singularly focused on big things and accomplishing those big things,” said outgoing Honolulu Councilwoman Kym Pine.��

Of course, the island is also in the throes of the COVID-19 pandemic to which the mayor has delivered a mixed performance.��

While the island fared much better than many mainland jurisdictions in terms of case counts and deaths, many people found the mayor’s pandemic response to be chaotic and, at times, ill-conceived.��

People who worked with Caldwell throughout his term said he was a dedicated, hardworking and hands-on mayor who genuinely loved the nuts and bolts of the job.

They said he cared deeply about how his decisions would impact people, that he was an attentive and encouraging boss who advocated for his staff and that he took criticism seriously, sometimes personally.����

In the end, Caldwell is handing off a lot of big problems to Mayor-Elect Rick Blangiardi, who will be sworn in on Saturday. The retired television executive, who has never held elected office, will be tasked with picking up where Caldwell left off.��

That includes pursuing the long delayed and far over-budget rail project, addressing homelessness that worsened under Caldwell and is only expected to increase, and rebuilding Oahu’s economy while also keeping people safe from COVID-19.��

While Caldwell started his tenure with relatively high approval ratings above 50%, they sank to around 30% in 2017 and have stayed there.��

Caldwell recently sat down with Civil Beat for an interview to talk about his tenure as mayor.

In his view, his administration embraced change.��

“We have not played it safe,” he said. “We have not looked for parades and then got behind the parade that is marching in front of us.”��

‘Build Rail Better’?

When history judges the Caldwell era, all other issues may be eclipsed by the rail, according to Colleen Hanabusa, the former congresswoman and Caldwell appointee to the Honolulu Authority for Rapid Transportation.��

“For an elected official, as far as the people are concerned, the bucks stops there,” she said.��

Caldwell was former Mayor Mufi Hannemann’s managing director in 2009 when the project took off prematurely, according to , costing millions of dollars in cost overruns.

And when Caldwell ran for mayor in 2012, he pledged to “build rail better.” At the time, rail was projected to cost about $5 billion, less than half the current estimate.��

Caldwell now says his promise to “build rail better” wasn’t realistic.��

“After getting over here and living through the ups and downs, it became clear that it’s very difficult for me to actually build rail better,” Caldwell said.��

Today, he often says that the mayor has all of the responsibility but none of the authority for rail, which lies with HART. Beyond appointing board members to oversee HART, Caldwell said all he can do is make his opinion known.��

He said he doesn’t have influence over HART’s decision-making or even access to its inside information. Several times, HART has given him information that turned out to be wrong, he said.��

“So the trust has disappeared,” he said. “Every number they’ve said has been too low and every schedule they’ve given has not been met.”��

As the mayor’s confidence in HART has declined, so has the public’s confidence in the mayor, who has gone from rail’s biggest cheerleader to backing out of the public private partnership that was supposed to get it built.����

Natalie Iwasa, a Hawaii Kai resident and city watchdog, said Caldwell should’ve been more candid about the project’s problems earlier.��

“He kept telling people, ‘We’re not going to have any debt when this is done,’” she said. “It sounded like it was all hunky dory. It was only in the last year or so he’s been bringing up concerns about the cost.”

As the city’s managing director under Hannemann, Caldwell supported the creation of HART to “get politics out of it.” If he could do it over, he said he would have kept rail under the city’s Department of Transportation Services. And if he had a third term as mayor, he said he would try to dissolve HART.��

Ernie Martin, an adversary of Caldwell as chair of the City Council, had advocated for dissolving HART years ago. He said the mayor should have gotten on board.��

“If we were more closely aligned back then, we would be in a better position,” he said.��

Now the project has an $11 billion price tag and an estimated completion date 13 years in the future – a timeline that would extend past even two consecutive Blangiardi terms.��

Despite all the project’s woes, Caldwell said that if he could do it all again, he would still pursue the rail.��

“I think it’s absolutely the right thing. If I didn’t, I wouldn’t be fighting for it my last three weeks, two weeks, one week, last day,” he said.��

“Every great city on this planet, it has a rail system and has grown inward instead of outward. And I believe for the sake of our island, for the sake of our state and our planet, we need to do that.”��

Homelessness Worsened Under Caldwell

Among Mayor Caldwell’s most controversial stances was his criminalization of homelessness. As for its effectiveness, the data speaks for itself.��

There are more people living on the streets of Honolulu today than there were when Caldwell took office.��

In 2013, the beginning of Caldwell’s first term, the annual point-in-time count identified 1,465 unsheltered people.��

In January of this year, that number was 2,346 – a 60% increase. That does not match up with downward trends on or .

Homelessness overall – both sheltered and unsheltered – is virtually unchanged since 2013: approximately 4,500 people.

“They have utterly failed at addressing homelessness on Oahu,” said Mateo Caballero, an attorney with the American Civil Liberties Union, which sued the city over its homeless sweeps.��

Throughout his tenure, the mayor supported the sweeping, or forced displacement, of homeless encampments – even during the pandemic, which the CDC advises against. His use of the term “compassionate disruption” for this practice struck many as Orwellian.��

Caldwell also backed criminalization measures like the sit-lie ban and sidewalk nuisance laws through which unhoused people receive criminal citations that cycle them in and out of the criminal justice system.��

To this day, he stands by that strategy despite academic evidence that it is counterproductive, criticism from advocates who say it is cruel and a Supreme Court decision that states it’s unconstitutional to punish someone for being homeless if there’s nowhere else to go.��

Caldwell noted that the city has acquired 2,508 housing units during his tenure for affordable housing and supported projects like Hale Mauliola Navigation Center, a transitional housing complex at Sand Island, and the Punawai Rest Stop in Iwilei where people can wash up, do laundry and get connected to services.��

The Caldwell administration and the City Council also passed affordable housing legislation in 2017 to incentivize developers to build more affordable housing. Pine, who was the zoning chair at the time Bills 58 and 59 passed, said the legislation made a material difference in creating more units.��

“If we had not done what we did, I think the numbers of homeless would be much greater,” Caldwell said.��

Caldwell did fund housing and homelessness resources in a way that previous Honolulu mayors did not. And Honolulu did make ��

But it’s clear that the city could have done much more.��

When the Caldwell administration from its own Housing First program, it found that the overwhelming majority stay housed and were less likely to use drugs or alcohol, get arrested or visit emergency rooms for health care.��

Despite these encouraging results, Honolulu funds only 315 Housing First vouchers, enough to cover only 7% of Oahu’s homeless population.

Overall, funding for housing and homelessness programs represent only a drop in the budget of the city’s nearly $3 billion operating budget.����

Caldwell-appointed Housing Director Marc Alexander has said that the city has done a lot to address homelessness but that the state needs to step up in the areas that the city, which lacks a health department, cannot: mental health and addiction treatment services.

Still, observers like Hawaii Sen. Stanley Chang, who chairs the Senate committee on housing, think the city could’ve done more.

“The solution is relatively clear: Building more housing and then subsidizing the homes for the people who can’t afford it,” he said.��

Caldwell “did increase the amount of resources going into programs like Housing First, but not enough to reverse the trend of increasing homelessness.”��

Pine said the mayor also missed a big opportunity to use federal CARES funds to build thousands of tiny homes to shelter homeless people and an expected influx of those who lose their housing because of the pandemic.��

That failure will have dire consequences when eviction moratoriums lift, she said.��

“You’re going to have entire families living out of their cars,” she said.��

‘Living With The Virus’

Caldwell’s last year in office has been dominated by the COVID-19 pandemic.��

The results have been mixed.��

The island shut down earlier than some other places, including the state of Hawaii, which appeared to pay off in the first half of the year when Oahu’s reported cases were in the single digits for weeks in April, May and early June.��

In the absence of state leadership in the areas of testing, contact tracing and providing isolation and quarantine facilities, Caldwell stepped up.��

Regarding testing, the mayor tried to strike a deal with a company called Everlywell. When that didn’t work out, he partnered with the University of Hawaii to launch a new lab that is, after some delays, processing COVID-19 tests.��

When a whistleblower revealed that Hawaii’s contact tracing system was insufficient, Caldwell endeavored to hire his own with the city’s CARES funds. He said a team of 130 city contact tracers is helping the state track the virus.��

The mayor has also secured rooms in hotels and other buildings so that first responders, homeless people and anyone else can quarantine if they’ve been exposed, or isolate if they’re COVID-19 positive.��

“We took strong initiative,” Caldwell said. “We fought hard. We didn’t give up, and we got them in place. And I think it’s made a difference.”��

Political observers, including doctors, agreed that Caldwell deserves credit for that.��

“I am grateful that we had a mayor who saw it as his responsibility to stop the spread of the virus, especially when the state effort faltered,” said Jonathan Dworkin, a clinical infectious diseases doctor who served on the mayor’s advisory panel. “That saved a lot of lives.”

However, many of the mayor’s pandemic rules felt nonsensical to the public and to scientists.��

At one point, public outdoor spaces – beaches, parks and hiking trails – were shut down. But indoor businesses including retail stores, restaurants and gyms that provide more person-to-person contact and less ventilation were open.��

Public health experts said the absurdity of it all eroded public trust, an essential element in any public health response.��

To enforce his mandates, Caldwell used the same approach on the general public that he had used on the island’s homeless population for years: He had the Honolulu Police Department cite people for minor infractions.

It didn’t go well.��

The ticketing spree put an added emotional burden on thousands of people and in the end, the city had nothing to show for it. Prosecutors dismissed tens of thousands of citations.��

Meanwhile, HPD officers have raked in thousands of dollars in overtime, a situation that resulted in some officers being criminally investigated.��

Notably, Caldwell allocated more federal money to the police than to providing relief to struggling individuals and families in the form of rent, utility and child care payments.��

While HPD officers now have brand new ATVs and trucks, as of mid-December, the city had not distributed all $25 million in the Household Hardship Relief Fund.

Overall, Caldwell said he made an effort to prioritize public health over all else, even if it meant tickets from the police or keeping businesses shut down.��

“Yes, there is this feeling of, we’ve got to take care of the economy,” he said.�� “But if you do it without a lot of forethought, you end up in the same place, and you end up in a worse place. We had 350 cases in one day.”��

In recent months, the mayor assembled a panel of medical experts. Along with the Department of Health, they helped him establish the existing tier system in which the island’s restrictions are predetermined based on the number of COVID-19 cases and the test positivity rate.����

The system, while imperfect, has brought some level of stability and predictability to the island’s pandemic response.

“I think the model we have actually is working because we are living with the virus now,” Caldwell said. “The public is, for the most part, compliant and being careful.”��

Caldwell’s Next Chapter

Caldwell leaves a lot of work unfinished, but there were notable positive developments on his watch too.��

The administration has paved 2,176 miles of roadway, according to the city.��

When the mayor came into office, road maintenance was a top complaint of residents. Chang recalls someone with a bumper sticker that said: “I’m not drunk, just dodging potholes.”��

“Today, road maintenance is not one of the top issues we get,” Chang said.��

At the beginning of the mayor’s tenure, Honolulu had over 100 sewage spills a year, he said. Last year, there were 31, according to the mayor.��

His administration restored bus routes that had been cut and began the process of converting the bus fleet to all-electric vehicles to reduce the city’s reliance on fossil fuels. He added protected bike lanes – despite much controversy – and partnered with Biki to provide accessible bike rentals on city streets.��

“There is no doubt that we’ve dreamed big in this administration,” Caldwell said.

The mayor never raised property taxes on single family homeowners and he is leaving the city with a strong bond rating. Under his leadership, the Honolulu Zoo got reaccredited, the city gained a nationally certified medical examiner and the police department got its first female chief.��

The city also cracked down on an issue that was, for many years, politically untouchable: short-term vacation rentals. Caldwell signed a new law last year that aims to return what were in-home hotels to the local housing stock.��

“Things that we’ve done, at times, were very unpopular,” Caldwell said. “But I think it’s for the long-term future of our island, our city, our country and our planet.”��

In his final weeks in office, Mayor Caldwell said he doesn’t want to leave. He wishes he could have a third term as Honolulu’s mayor, but the law limits him to two.��

“For me, I think the job of being mayor is probably the greatest job you can do in public service,” Caldwell said. “You can make a difference quickly and have lasting impact. I wish I could keep doing it. It’s a bittersweet time.”��

Former Council Chair Ikaika Anderson, a close friend of the mayor, said Caldwell did the best job he could.

“Like anyone else he has faults,” Anderson said. “But when people ask for help and he’s able to help, he does.”��

The outgoing mayor said he doesn’t have a job lined up, but he’ll stay busy.

He will continue to serve as a paid member of the board of Territorial Savings Bank. The mayor’s side gig has been a point of contention and ethical concern over the years, but he says it just gave him an opportunity to stay sharp in the area of banking and finance, which used to be part of his law practice.

“It’s a break from everything else I do,” he said.��

He’s thought about writing a book or two. One idea is a book about the rail project.��

“Large infrastructure projects are something I’m very passionate about,” he said.��

Caldwell is also thinking about writing a book that would highlight “people showing incredible courage during the pandemic.”��

The mayor has considered teaching too, either at the University of Hawaii law school or college-level public policy courses. He may also return to the island of Hawaii, where he grew up, to visit with his brother and sister and camp and fish at South Point. He also wants to fly to Maui to see friends and hike.��

He also has unfinished business at his home, which he shares with his wife Donna Tanoue. And of course, he’s considering that run for governor in 2022.��

“But first, I’m going to decompress. Take a breath,” he said. “We’ll see. One step at a time.”��