Charlie Hales had been on the job less than 48 hours. His inaugural act of power was already reverberating.

Portland's 52nd mayor opened his first City Council meeting in January 2013 by resisting $395,000 for a nonprofit helping at-risk youth. It was the type of painful choice Hales promised as a back-to-basics mayor focused on necessities.

But he miscalculated.

First, Hales had suggested growing the same program during his campaign. He never sought support from city commissioners, who'd already approved the spending. And Hales wasn't ready for a fight from angry advocates.

Hales buckled and restored half the money. And, in a telling move, he doubled down by supporting similar efforts over the years.

The episode marked the first sign of the tension that would mark Hales' tenure -- and his struggle to chart a consensus course for a city overtaken by rapid change.

Hales led Portland during one of its most prosperous eras, with people flocking to the city to live in dense apartments near streetcar lines Hales championed as a city commissioner in the 1990s and early 2000s. But the Rose City's rise also brought trouble Hales wasn't prepared to handle.

Housing and rental prices have skyrocketed. And Portland shared in national struggles to address homelessness, restore confidence in police and control gang violence. Too often in the face of those problems, according to interviews with two dozen government insiders, community activists and business leaders, Hales seemed reactive, combative or adrift.

Next month, he'll become Portland's third consecutive mayor to leave after one term -- four years marked by a propensity for diving into contentious topics without a clear path forward, zig-zagging on policies and ignoring his own "measure twice, cut once" mantra.

Hales arrived as a self-styled City Hall savior who would govern with a steady hand and avoid the scandal and breathlessness of his predecessor, Sam Adams. He thrived early, relishing the nuts and bolts of planning, budgeting and inking game-changing development deals.

Charlie Hales

Who:

Portland mayor, 2013-2016; city commissioner, 1993-2002

Age:

60

Wife:

Nancy, director of First Stop Portland, dubbed the "first lady"

Known for:

Streetcar, dense development, back-to-basics services

What's next:

Plans to fight climate change

Self-reflection:

"If I had everything to over again, I would lay more groundwork and spend more time upfront bringing people along."

Fondest memories:

Hosting USA Track & Field Indoor Championships, talking to president about livable cities, inspiring youth. "The who-gets-to-do-this moments in city government. Having lunch with the Dalai Lama and having him talk with Nancy about her program at Portland State. I mean, pinch me."

But he soon struggled to shape a broader vision. He sparred with colleagues and the media as fights over street fees and homeless camping entangled him. It wasn't until late in his term that Hales found footing, branding himself as a voice against climate change.

"He really excelled in putting foundational stuff in place that will give major dividends later on," said Zari Santner, the city's former parks director and a longtime Hales supporter and friend. But on Portland's most pressing issues, "people wanted immediate response and immediate results," she said, "which is not possible."

In a surprising move last year, Hales dropped his re-election bid two weeks after the city's past three mayors endorsed his challenger, Oregon Treasurer Ted Wheeler. The biggest blow came from Vera Katz, Portland's last multi-term mayor, who had supported Hales' first mayoral run.

"I'm not satisfied" with his performance, Katz, who left office in 2004 after three terms, told The Oregonian/OregonLive this month. "I don't think he's taken the job seriously enough. There are a lot of challenges in the city, and you've got to take each one of them on and find solutions or begin to find solutions. And he hasn't done that."

Hales dismisses the critique -- and once more punched at the press.

"I suspect Vera does not know all that has been accomplished here," he said in a nearly 90-minute interview in his mayoral suite, pointing to a seven-page checklist created by aides. "It's difficult for people to keep track of what's happening in City Hall with the news environment that we're in today."

Hales highlights his work overseeing federally mandated police reforms, restoring trust in city spending and expanding opportunities for kids to keep them away from gangs, including $2 million a year for community centers, even if those results aren't immediately tangible.

"I've been on a mission to get a lot of stuff done. I would submit that we have," Hales said. "Probably more than in any other four years of any administration," he continued, pausing for effect, "in terms of actual ... things ... done."

Introducing Mr. Fix It

PORTLAND, OREGON - Nov 6, 2012 - Charlie Hales and his wife Nancy take the podium during his election night party at the Holocene night club in Southeast Portland. Propped on the lectern: a tool belt.

Hales fully embraced his Mr. Fix It persona on Election Day 2012. Propping a tool belt on the lectern at his victory party, he pledged to minimize drama and maximize results - a not so subtle shot at Adams.

He'd campaigned as an experienced leader who would pave streets and build sidewalks, curb runaway water and sewer bills, and fight for a high-quality school in every neighborhood.

Four years later, Hales remains in character.

Unprompted, he walked toward his City Hall desk on a recent Friday to once again grab his tool belt, beginning a wide-ranging interview with The Oregonian/OregonLive by plopping it down in front of a reporter. He then offered a hand-written note with 10 things he's "fixed" and proceeded to speak for 13 minutes without being asked a question.

Portland Mayor Charlie Hales crafted a Mr. Fix It persona, complete with a tool belt. Here's his hand-written list of fixes.

"I think I can rightly claim that my billing as a fix-it guy was accurate," he said.

Hales' first task was Portland's woebegone budget and an unprecedented $21 million shortfall. All things considered, he made it look easy.

He pressed city bureaus and politicians for unpopular cuts, including to police and fire, which typically had been spared. He forced the City Council to stop paying for annual programs with one-time money. The next year when the economy improved, he showed discipline by paying off old debts.

"These are decisions that no mayor, since I've been here, has been willing to make," said the city's budget director, Andrew Scott, who has worked under four mayors.

Hales scored a string of victories, many predicated on reversing political decisions from Adams' administration.

He pushed the city's transportation bureau in 2013 to resume preventive maintenance on crumbling neighborhood streets, claiming 100 miles a year of paving and sealing work.

He partnered with Commissioner Nick Fish in 2014 to defeat a ballot measure that would have stripped water and sewer oversight from the City Council. And Hales shut down two urban renewal districts a year later while keeping a promise to help Portland State University redevelop.

Hales also succeeded as the city's planner-in-chief. He shepherded through a years-long effort to lock in where and how development will happen over the next 20 years.

"That's huge," Commissioner Amanda Fritz said. "I don't think people realize how much work Charlie himself put in."

Meanwhile, the city's urban renewal agency signed a long-sought deal to buy the Pearl District post office for redevelopment - something that escaped a generation of mayors. Hales also pushed for action in east Portland's neglected Lents neighborhood, where four projects are in the pipeline.

"It was unconscionable that we owned all this property in Lents yet no dirt was turning over," Hales said.

In Lents, as with other deals, obstacles emerged that could have prompted Hales to abandon ship. He didn't.

"He's not as political as maybe he ultimately could be in the job," said Patrick Quinton, former director of the Portland Development Commission. "He believes in certain things, and so he follows through."

Making mistakes

June 3, 2014 - Portland Mayor Charlie Hales and Commissioner Steve Novick spoke to the media Thursday morning about a proposed street fee to pay for maintenance and safety improvements across the city. Beth Nakamura/ The Oregonian

But once Hales no longer had Adams' ghost to challenge, his image as a get-it-done mayor seemingly unraveled in the span of 50 weeks.

Remembering Mayor Charlie Hales

Police contract:

Hales passed a new police contract this year with higher pay to help recruit and retain officers. He showed perseverance, winning unlikely political support. "The need to do it got clearer and clearer," he said.

Street fee:

A plan to pay for street repairs in 2014 imploded, prompting an unsuccessful recall attempt against Hales. Hales said he wished he could do it over, but added, "I'm willing to raise those uncomfortable questions, often about taxes."

Community centers:

Hales set aside $2 million to provide free access at community centers, hoping to curb gang activity. Parks officials tallied about 6,000 visits in summer 2015 and 9,000 this summer. Gang-violence calls hit their highest levels in 2015 since tracking began in 1998, and this year was second-highest.

"Can I show you an analysis that proves that we have less gang violence than we would have had because we have thousands of kids in community centers?" he said. "No. But I think it passes the common-sense test."

Old Town/Chinatown:

Led by Hales, the City Council in 2014 approved a five-year plan pledging $57 million in urban renewal money. So far, just $2.7 million has been spent. "With or without public money," Hales said, "there's a renaissance happening there."

Housing emergency:

Hales declared a housing emergency in September 2015 and committed $20 million in city money, a major investment. Although Multnomah County is a necessary partner, the chairwoman didn't receive a call from Hales until the morning of the announcement. "There have been some cases where I have led quickly and early," Hales said. "I will admit, sometimes not with as much collaboration as I should have."

Sidewalks:

During his campaign, Hales called specific attention to Southeast 117th Avenue for not having a sidewalk, saying, "That's not OK." Today, there's still no sidewalk. Hales said he's pushed for sidewalks in other areas of east Portland but, because he owns a rental home near 117th, it would be inappropriate to advocate there.

Fossil fuel ban:

After reversing support for propane export plant, Hales doubled down and banned new fossil fuel storage facilities larger than 2 million gallons. "This is good work," he told supporters last week, "and it will make a difference."

Problems began in late May 2014, when Hales and Commissioner Steve Novick proposed new fees to pay for street improvements. Hales offered no public process and wanted the City Council to say yes two weeks later.

Residents flipped out. Business leaders vowed to fight. The effort imploded. Hales and Novick offered five different plans before dropping it - a theme for the mayor, who later pitched then punted taxes on businesses and home demolitions.

Flash forward a year. Though Hales had welcomed a new propane export facility on the Columbia River, he rescinded support for Pembina Pipeline Corporation in May 2015.

He said Pembina "failed to make the case" environmentally, eight months after declaring it would help the economy while meeting the city's high environmental standards.

He never recovered, especially with the business community. Discontent with Hales opened the door for Wheeler's challenge. Political support waned by summer 2015, with polling for Wheeler showing Hales trailing. More than half of surveyed Portlanders felt Hales' performance was fair or poor.

Tim Boyle, Columbia Sportswear's chief executive, was among some two-dozen donors who supported Hales' 2012 mayoral bid before switching to Wheeler.

Boyle recalled having "fairly heated arguments" with Hales, including about the street fee. Boyle said Hales too often shut out Portlanders' opinions.

"Some people can handle criticism and some people can take it as constructive opportunities to at least hear another opinion," Boyle said. "But when we had a few screaming matches, I was concerned my particular opinion ... wasn't going to get much traction."

Hales said he's not a yeller. Speaking generally, he said, "I think that is somebody perceiving hard words as loud words."

No one disputes that Hales' relationships inside and outside City Hall were less than ideal.

Hales began his term by flexing one of his only powers in Portland's commission-style government, sidelining the council by taking over every city bureau for four of his first five months. He then asked commissioners which assignments they'd like, only to hand out duties without necessarily catering to those desires.

Novick, a Hales ally, said the move created enmity with Fish, who lost the city's parks and housing bureaus. Novick said Fish's underlying instinct was to oppose Hales whenever an opportunity presented itself.

"He did make some mistakes in relationships as mayor," said Novick, who lost his own re-election bid last month. "The biggest one was taking away Nick Fish's bureau assignments, which made Nick into a permanent enemy." In that way, Hales wasn't as sensitive to mayor/commissioner dynamics "as I would have expected."

Fish said he "started strong" with Hales but then "kind of drifted," taking some of the blame. But he vehemently denied being an enemy or targeting Hales for opposition.

"In retrospect, I wish we had talked more, and I wish we carved out more time for one-on-one meetings," Fish said. "Because I've found with Charlie, those are always the most productive."

Council relationships got so bad that Hales and commissioners essentially held a therapy session in April 2015, using a daylong "retreat" to privately hash out differences.

Hales' relationship with the city's influential chamber of commerce was also left in tatters.

For years, the Portland Business Alliance has typically met with Portland's mayor on a monthly basis. But under Hales, meetings frequently were canceled, said Sandra McDonough, the group's chief executive and president. Then, in fall 2015, Hales decided to meet only as-needed.

"In our view, the signal was pretty clear," McDonough said, with Hales "basically saying we don't need to meet."

And so they didn't.

Hales, meanwhile, countered that the business group "has opposed almost every progressive thing that the city of Portland has done in the last four years, and offered few constructive alternatives to progress." Meeting with business leaders "hasn't been productive."

Hales also had a rollercoaster relationship with the media, offering thoughtful answers during interviews but also prone to publicly condemning the media for problems he helped create.

He blamed a "slow news week" in 2013 when The Oregonian/OregonLive revealed questionable financial moves that pushed Hales to fire the city's top administrator, Jack Graham. And this year, he again charged a "trial by media" over revelations that then-Police Chief Larry O'Dea accidentally shot a friend during a camping trip in eastern Oregon.

Hales said assailing the media hasn't served him well.

"No, because it made people in the news media mad at me," he said. "I tried to call things like I see them."

Evolving leadership

Portland Mayor Charlie Hales announces details of a declared housing emergency. Kristyna Wentz-Graff/Staff

Hales' evolving priorities left him open to criticism and praise.

In 2013, when negotiating a police contract, Hales claimed the rank-and-file Portland Police Association was trying to shut out the public with "backroom bargaining (sessions) at the very time transparency is most needed."

But this year, Hales made no such push as he worked behind closed doors to deliver higher pay in hopes of recruiting and retaining more officers.

Protesters decried the secrecy and stormed City Council the day of the contract vote. The hearing moved to a private room, with activists pepper-sprayed on the steps of City Hall.

Hales said neither side figured out how to make a public process work in 2013. "It turned out to be theater," he said. "My regret is thinking it could be done in public."

Portland's elected auditor, Mary Hull Caballero, said Hales resisted oversight and accountability measures. She said he showed little urgency over a leak to the police union that undercut a civilian police investigator. The leak disclosed past behavior reported in a confidential background check.

She also cited Hales' lack of disclosure to her Independent Police Review Division about O'Dea's shooting.

"The ethical tone of an organization is set from the top," said Hull Caballero, who serves as the city's watchdog. "The city is in a worse place because of his lack of leadership."

Hales declined to directly address the auditor's comments, saying he wouldn't publicly slam a colleague. But he insisted he's made top-to-bottom reforms.

"We have fixed the police bureau," he said, pointing to a 32 percent drop in officers' reported use-of-force cases against individuals since 2012.

Hales' response to housing and homelessness was another flashpoint.

Affordable housing advocates pressed for extra funding last year, but Hales was reluctant to dedicate more money from urban renewal. He worried that might limit future redevelopment opportunities. In the end, Hales and the City Council approved $67 million more for housing over the the next decade.

"Urban renewal, I think, speaks to the old Charlie very well," said Commissioner Dan Saltzman, who oversees the housing bureau. "It was part of his transformation, and part of his journey. He ultimately got there."

In September 2015, Hales declared a hastily conceived housing emergency, setting off a months-long debate about tent camping and shelter beds. His chief of staff at the time, Josh Alpert, devised it one Sunday night while poring over city regulations, a glass of scotch in hand.

Hales announced it three days later.

"It absolutely was a rush job, and I don't regret that," Alpert said. "We were trying everything we could."

Tents soon sprouted across the city, emboldened by Hales' lax enforcement and a "safe sleep" policy allowing some overnight camping. Most tents never came down at daybreak.

It was a remarkable turnabout for Hales, who in his first year had shooed campers from City Hall and talked about an "epidemic of panhandling and homelessness."

Business groups sued, and Hales retreated, saying the policy was misunderstood.

Jim Mark, chief executive of the Melvin Mark real estate companies, said the uncertainty caused by Hales' policies has been "disastrous." Of Hales in general, he said: "I think he's been a fairly poor mayor."

But Deborah Kafoury, Multnomah County's chairwoman, defended Hales.

Homelessness hadn't been a central theme when he ran for mayor, she said, but he responded. Through a partnership with the city, Multnomah County has expanded its shelter capacity over the past year by 550 permanent beds.

"I would argue he's done more for the issue of homelessness than any mayor," she said.

Hales said he's felt more free to focus on volatile issues since dropping his re-election bid.

"People may not like some of the things I'm doing, but they have to come up with another reason not to like it, other than, 'He's just running for re-election,'" Hales said. "And that's been delicious."

Sailing away

Portland Mayor Charlie Hales with activists and students who supported the city's vote to ban new new bulk fossil fuel storage terminals on Wednesday at City Hall.

As Hales prepares to exit, he's found a new calling: fighting climate change.

After flip-flopping on Pembina last year, Hales traveled to Rome and heard Pope Francis speak about the need for environmental action. Hales read the pope's nearly 200-page encyclical and came away with "a reawakening."

Environmental advocates saw a difference. Bob Sallinger, conservation director for the Audubon Society of Portland, said Hales was generally "more effective at stopping bad things" than "putting forward a positive vision."

But Sallinger credits Hales for recent efforts. Last Wednesday alone, Hales celebrated a policy trifecta: new rules to disclose energy scores for homes, a plan for government to add electric vehicles, and the nation's first ban on new fossil fuel storage facilities.

"That was a courageous step," Sallinger said. "He showed a lot of growth."

Hales, who turns 61 next month, said he's not ready to retire. His next chapter, he said, will focus on "the intersection of climate action and local quality of life." It's an ironic coda, given that Adams, whom Hales used as a foil, became U.S. director of the climate-focused World Resources Institute.

Hales didn't rule out a job with C40, a climate change group focused on big cities. That's where his former top aide, Alpert, now works.

No matter. Hales has time to decide.

He's leaving Portland on Jan. 2, less than 48 hours after Wheeler takes over, for a sailing excursion spanning 18 months. He'll hit the Panama Canal on his 44-foot boat in March, the Western Caribbean in April, leave Miami in May for the Atlantic Ocean, then stay in the Mediterranean through November with his wife, Nancy.

He's expecting stops in 25 countries as far east as Italy, and as far from today's go-go news-and-social media scene as possible.

"It's something I've always wanted to do," he said of the trip. "And you don't get too many points in your life where you can say, 'I've got a clean break between one job and the next.'"

-- Brad Schmidt

503-294-7628

@_brad_schmidt