On December 10, exactly three weeks from Mayor Charlie Hales’ last day in office, Portland solved veterans’ homelessness.

Sort of.

Thanks to years of work (and millions in federal dollars), officials announced December 10 that no veteran who needs a home in Multnomah County these days has to wait more than three months for housing. Portland’s the only West Coast city that can say that.

The accomplishment belongs to many people, but for a late-term mayor who’s been battered by homelessness like no other issue, it was a very big deal. Hales recently told the Mercury that the announcement is a high point of his four years in office. “Not just because it’s cool we got the national recognition,” he said, “but the sheer human impact.”

It’s not hard to imagine a vast segment of the city rolling its eyes at that statement—and for starkly different reasons.

Depending on your point of view, Hales might be a weakling who laid out a red carpet for the homeless and coddled illegal encampments sprouting up around town. Or he might be a double-dealing tyrant who allowed his cops to arrest people for merely trying to live, and who ordered up the largest camp sweep in the city’s history.

Either way, there’s a good chance you’ll remember Hales for how he addressed the homelessness crisis that Portland will be grappling with for years to come.

So as the mayor prepares to literally sail off into the sunset next year (he’s planning to pilot his boat to the Caribbean and Mediterranean), the Mercury decided to look back at how Hales handled the problem—and whether he helped or hurt.

Hales beat out a crowded field in 2012 by hoisting a tool belt.

The gimmick had roots in his background as a builders’ lobbyist, but its appeal had nothing to do with the frantic push for new homes, shelter space, and houseless villages that would dominate the second half of Hales’ term.

Instead, it was a nod to the humdrum promises of competent stewardship Hales said he’d bring. In those days, he preached the reliable gospel of “schools” and “police” and “roads.”

An early Hales mantra—“Minimize the drama and maximize the results”—might be easy joke fodder these days. But in 2012, no one giggled.

Meanwhile, homelessness was a nonfactor during the campaign. Hales ascended to the third floor of City Hall in January 2013 every bit the business-backed mayor he’d appeared to be. And for the first half of his tenure, the transportation wonk nicknamed “Choo Choo Charlie” might just as well have been called “Shoo Shoo Charlie.”

“Hales took office with a mission to sweep the downtown,” says Vahid Brown, a homeless advocate who would work closely with Hales’ staff in the years to come. “That was how he began his relationship with this issue—as a very traditional, conservative mayor.”

Hales first went to war with the group of campers who’d been staying outside of City Hall in protest of the city’s anti-camping ordinance—some of them holdouts of the Occupy Portland protests of 2011. He used pressure washers to clean the sidewalks, put restrictions on the hours people could sit in front of the building, and stood before news cameras to talk up the sweeps surrounded by high-ranking cops, not housing officials.

“We’re not going to wait until homelessness is solved to start working on lawlessness,” he said. “Or else we’ll wait a very long time.”

Hales didn’t stop there. While complaints over homeless camping poured into his office, he oversaw the police bureau as it rolled out a controversial effort that aimed to more easily arrest people committing nuisance crimes like urinating in public. The plan was ultimately scrapped after it turned out cops were using it to arrest people merely for sitting on the sidewalk, but a similar policy would later be used to justify the arrests of Portland campers.

All that enforcement, of course, wasn’t doing anything to abate Portland’s fast approaching homelessness crisis.

In early June 2015—nearly a week after Hales authorized a massive push by police to clear “entrenched” campers out of the Central Eastside—officials released their latest “point-in-time” homeless count.

It showed homelessness had increased by roughly four percent in the last two years. The number of unsheltered Portlanders detected by the count had remained static at about 1,890, but officials noted an alarming increase in unsheltered women and African Americans.

The report also suggested that as many as 16,344 people might be doubled up on the couches and floors of supportive family or friends—a sign that an immense issue was lurking below the staid surface.

Today, Hales readily acknowledges having a skewed view of the homelessness problem during the first part of his term.

“My working assumption was it was a livability problem to be managed, as opposed to an affordability and humanitarian crisis that I had to run toward,” he says.

The first major shift in that stance—and undoubtedly one of the most important moments of his time as mayor—came roughly 20 months into Hales’ tenure, as public outcry over ever-more-visible homeless camps was increasing.

On September 23, 2015, shortly before city council was scheduled to meet, Hales and his then-chief of staff Josh Alpert could be seen popping into city commissioners’ offices, briefing the council members on something urgent.

The subject soon became clear. Hales abruptly announced at the beginning of the meeting his intention to declare a “state of emergency” around housing and homelessness.

“When I came into office, the single-night count of homeless told us we had 1,800 Portlanders sleeping unsheltered. That same count, two years later, barely budged,” Hales said at the time. “We’ve tried slow-and-steady. We’ve tried by-the-book. It’s time to add the tools we currently lack.”

The idea for an emergency—like many ideas to come—was hatched by Alpert, who says he’d spent part of the previous weekend sipping a Scotch and going over the city code to seek out new ways Portland could battle homelessness. Under an “emergency” declaration, he learned, the city’s steep zoning regulations could be shrunk to nothing, in theory making it easier than ever to ramp up homeless shelter space.

“It was clear the emergency provisions would allow us massive amounts of flexibility,” Alpert says today.

The declaration proved a rare beast for Hales.

“When you cut corners, it sometimes bites you in the ass.’” —City Commissioner Nick Fish

Often when the mayor attempted a big shift without giving his council colleagues much warning, he faced pushback.

As Commissioner Nick Fish puts it, “The time you spend vetting things with your colleagues is time well spent. When you cut corners, it sometimes bites you in the ass.”

Not so in this case. Hales had widespread support by the time his pronouncement was a week old.

In a news conference presided over by the mayor, Multnomah County Chair Deborah Kafoury, and an array of other elected officials and housing advocates, a loose plan was offered up. Officials pledged to put $30 million into a new strategy crafted by A Home for Everyone, a coalition Hales, Kafoury, and others created to tackle the problem.

Officials said their plan could cut the city’s homelessness crisis in half by 2017—largely by creating more housing opportunity and boosting rent assistance and services for people on the margins.

“The world shifted when we declared a housing emergency,” says Fish, who has clashed with Hales more publicly than any other member of council. “It had the benefit of focusing our attention on the number one problem facing the community. And it gave us license to try new things.”

Even Hales’ staunchest critics point to the emergency as a bright spot. More than a year after that press conference, it’s helped pave the way for roughly 550 new shelter beds, unprecedented public money for affordable housing (including the passage of the city’s first-ever housing bond in November), renewed commitments of at least $30 million a year to battle homelessness, and more.

It appears highly unlikely that homelessness has been “cut in half,” as officials pledged—or anything close. The first point-in-time homeless count since 2015 is scheduled next month, and most people the Mercury spoke with expect the number of homeless people in Multnomah County to have risen.

“They opened up some shelter beds—the city and county deserve credit for that,” says Chris Trejbal, chair of the Overlook Neighborhood Association, who’s repeatedly criticized Hales’ lenience with homeless camps. Otherwise, Trejbal says, “I think he was a failure.”

If the emergency declaration was one fulcrum that helped shift Hales’ policies, a potentially more important one emerged on the edges of North Greeley, just after Thanksgiving 2015.  

That’s the date Hales and his wife, Nancy, visited Hazelnut Grove, a community of homeless Portlanders who’d been pushed around in previous sweeps but were now making a stand. Since the housing emergency declaration, the group had grown bolder—increasing in size and organizing into a community with a governing body and a code of conduct.

The city had already scrapped plans to sweep Hazelnut Grove once by the time Hales made this pilgrimage (officials would later acquire land from the state in order to allow campers to remain). And when a reporter showed up and asked Hales what he thought, he sounded excited.

“I’m impressed by how it is working,” he said.

It might have wound up being a hollow statement, but Hales had company that day. Alpert had previously visited Hazelnut Grove, and was inspired by this new model for short-term living. Now, his boss was voicing public support.

“That was the first time he saw what the community could do,” Alpert says. “I felt like I had backing from him to be somewhat politically bold.”

That boldness came on quickly.

In late October 2015, after Oregon Treasurer Ted Wheeler began campaigning aggressively for Hales’ seat, the mayor reversed course and decided not to run for re-election. Released from the burden of appeasing voters and donors, he got to work (or at least gave Alpert the green light).

Hales’ office ordered the purchase of two shipping containers, retrofitting them into storage spaces where homeless people could drop their things during the day (a first). It opened a shelter near Multnomah Village, in an unused Army Reserve building—transporting homeless people there and back in shuttles (another first). It spent money providing portable toilets and trash services to Hazelnut Grove and a similar camp, Forgotten Realms.

It did these atypical things in atypical fashion.

Rather than pushing the initiatives through the Portland Housing Bureau—which had coordinated homeless services since its inception, but which Hales did not control—Hales and Alpert ran them through the city’s Office of Management and Finance. That ensured they had day-to-day oversight of their experiments. It also rubbed some people the wrong way.

“It was a mistake to create a kind of shadow housing bureau in the mayor’s office,” Fish says today. “It essentially meant that people were playing out of position.”

Those early efforts paled in comparison to the bombshell Hales and Alpert dropped on February 8 of this year. That day, showing little interest in his colleagues’ opinion on the matter, Hales announced he was upending the city’s stance on homeless camping.

Under a new set of “safe sleep guidelines,” homeless Portlanders would be assured they could spend the night on sidewalks and certain “remnant” pieces of city property as long as they abided by some rules. They had to remain in groups of six or fewer, for instance, and they had to clean up their tents or sleeping bags in the morning.

“They were an attempt to have a common sense understanding that while we have more people camping than we have shelter, we need to accommodate the reality that they’re there,” Hales says. “We have no place for them to come inside.”

Homeless advocates, who’d been making the same point for years, were elated.

Monica Goracke, an attorney for the Oregon Law Center who frequently represents homeless people, called it “the most comprehensive, progressive, and deeply rational proposal that has ever come from City Hall on this issue.” The National Law Center on Homelessness and Poverty considered highlighting the policy at conferences.

But trouble quickly arose, with Hales’ office struggling to communicate its rationale to a public that began to view every tent that sprang up as evidence Hales had completely legalized camping.

“For some it meant ‘camp anywhere you want,’” Hales says. “For others, it was ‘you have to be out by morning.’ There was never a consistent or shared understanding.”

At the same time, the policy fell far short of its promises to move people who weren’t following the rules. Privately, mayoral staffers groused that city cops had thrown up their hands and weren’t especially helpful.

It all came to a head on the Springwater Corridor, the Southeast Portland multi-use path that’s played host to homeless campers for years.

In short order, large numbers of campers who’d been spread out on the trail began congregating near where the path crosses SE 82nd—not far from the Clackamas Service Center, where many got daily meals.

“People, I think, felt like they’d been given the green light to be open in their camping,” says homeless advocate Brown, who’s worked extensively with people living off the trail. “It exploded.”

By April, a coalition of business groups had filed suit to stop Hales’ safe sleep policy, citing the situation on the Springwater. The mayor formally rescinded it in early August, acknowledging it had backfired—an opinion Hales still holds today, and with which many agree.

Others see good in the mayor’s unpopular gambit.

“People can look back and say, ‘It’s a disaster’ or ‘he flip-flopped,’” says Israel Bayer, executive director of

Street Roots. “But it made people care enough to think about housing.”

Then, in September, Hales showed a little of his old self.

Not long after a high-profile fire and shooting at Springwater encampments, he marshaled forces to clear out the trail, in what is almost certainly the largest homeless sweep in city history.

“It got to the point where it was untenable, unsafe, and therefore unsustainable,” Hales says.

Still, some took the sweep as inconsistent with the mayor’s recent liberal policies. Activist groups vowed to help the homeless remain in place, if they wanted. Goracke, the attorney who’d praised Hales’ safe sleep policy, threatened to sue if the city didn’t give people more time to clear out.

Once again, the mayor was facing furious accusations that he didn’t care about the city’s homeless.

“It was not helpful and it has not made things better,” says Lisa Lake, a local homeless advocate who helped found the group Boots On the Ground PDX.

For many, the safe sleep experiment might be what Hales is most remembered for. That’s fitting, since the policy was emblematic of his high-profile efforts: experimental, concocted with little input from his council colleagues, forcefully pushed, and pulled back amid controversy.

“I think he did it with the best of intentions,” Lake says. “But I don’t think he did it with the intention of full follow-through.”

Alpert, the architect of the policy, admits it had flaws. But his take is different.

At a time when much of the nation—and especially the West Coast—is floundering on the homelessness fight, Alpert says, “it is the mayors who are willing to push forward, try new things, and aren’t afraid to fail who are going to find success. Mayor Hales is absolutely at the head of that pack.”

Here's something no one remembers about the safe sleep policy: It was introduced with a bunch of other provisions.

Also included were proposals to make it easier for people to live in RVs. And maybe the oddest bit was a plan to mass-produce “sleeping pods” that could be sprinkled on parcels of land throughout the city, creating small villages for the homeless.

And those pods? They might outlast Hales’ term, taking root as he sails the globe.

On December 14, homeless advocates with the city and county trudged through a snowstorm to a historic firehouse in Kenton. There they pitched skeptical neighbors on “Argyle Village,” a cluster of 14 professionally designed tiny homes that officials hope to relocate to a disused lot near Kenton Park.

Kenton residents met the sales pitch with skepticism—but also with, apparently, open minds. If the city can convince them, it’s likely Mayor-elect Ted Wheeler—once Hales’ bitter political foe—could oversee the creation of a first-of-its-kind Portland community largely attributable to his predecessor’s willingness to fail.

Asked about that failing, Hales isn’t shy. At one point in a recent interview, he launched into a story about a friend of his, who was staying at a Warm Springs resort some years ago when a grass fire broke out and began to rage.

“Some people tried to run away from it and died, and my friend ran toward it to help, and lived,” Hales said. “To me the homelessness issue has been a bit like that. It’s a case of running toward the fire, knowing that it’s going to hurt, but knowing that’s the only way.”

Hales' office has been circulating a list of his accomplishments. You can read it here. [PDF]

Grading Hales On Homelessness

Israel Bayer, Street Roots executive director: “Solid B , B+ ”

“An A for effort and a C for planning. There were good intentions there. You’re talking about a systemic problem that the smartest people in our community have no clear solution for. Overall he’s done more for people on the streets in the context of moving the issue forward than the vast majority of mayors in America.”

Shannon Singleton, JOIN executive director: “Probably B-, C+ ”

“There are some policies that have been an A, and there are some that have been a D. I do think that the unprecedented funding was really amazing. That allowed us to do and start some new things in the community.”

Deborah Kafoury, Multnomah County chair: B

“It’s hard to say overall. There are some areas that have been really good, and there are some areas that have needed work.... I didn’t always agree with every decision the mayor made, but to his credit he was willing to try new things. He was willing to admit when he was wrong.”

Vahid Brown, homeless advocate, Clackamas County housing policy coordinator: Declined to give a grade

For Brown, many of the positive initiatives from Hales’ tenure came from his former chief of staff, Josh Alpert. He notes: “It’s not like Josh was an autonomous agent. The mayor gave him the latitude to do that.”

Nick Fish, city commissioner: “I don’t give grades.”

“It wasn’t a big challenge for us during the recession to use Section 8 vouchers and put people in emergency shelters. What Charlie dealt with was the next wave of the problem, which was a set of market forces that acted with a vengeance.... For the things that have gone well, Charlie deserves his fair share of the credit. For the things that didn’t go well, he’s the mayor—he deserves his unfair share of the blame.”

Michelle Cardinal, CEO of R2C Group and a past critic of lax camping enforcement: C+

“But I think his heart’s in the right place. I would have loved to see him really rally the city council to get something done. It would be unfair to say he was a flop.”

Chris Trejbal, chair, Overlook Neighborhood Association: D

“They opened up some shelter beds. That’ll get you out of F territory... I think he was a failure. What we saw was an autocratic approach from the mayor’s office that didn’t want to engage the community writ large.”

Josh Alpert, former chief of staff: “I’m not going to give a grade.”

“He said, ‘Go out and try to figure this out, and when you need me come get me.’ For any politico working in any office, that’s the dream.... At a time when almost all mayors, not just in the US, but around the world, are struggling on these issues, it’s the mayors who are willing to push forward, try new things, and aren’t afraid to fail who are going to find success. Mayor Hales was absolutely ahead of that pack.”

Dan Saltzman, city commissioner: A-

“I think he became a champion sort of unwillingly, or certainly not knowing that was going to be a hallmark.... When Hales came into office, he was pretty much in my opinion a transportation and infrastructure guy. He quickly became ensconced in housing and homelessness, and rose to the challenge.”

Jeff Woodward, homeless advocate: F

“It’s nothing personal. He gets his F from his lack of transparency, his inability or unwillingness to meet with the community. He made these huge unilateral decisions like legalizing the safe sleep policy.”

Ted Wheeler, mayor-elect: "Absolutely will not" give a grade.

“I believe Charlie's intentions were good... I think it's okay that the mayor went down a couple roads only to find they were dead ends. It was a learning process. My administration benefits from that.”

Charlie Hales, mayor: C- for the first semester, A- for the second semester”

“During the campaign, I think my working assumption was it was a livability problem to be managed, as opposed to an affordability and humanitarian crisis that I had to run towards.... I’ve been shouted at from both sides. What I’ve really done is forged ahead hard.”