Josh Alpert, Charlie Hales' Chief of Staff, Is Leaving City Hall

Josh Alpert—Heading out of City Hall.

Josh Alpert— Mayor Charlie Hales' chief of staff and the central architect of the city's new strategies around homelessness—is leaving City Hall next month.

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After 11 months as Hales' top deputy, Alpert tells the Mercury he's accepted a job with London-based C40 Cities Climate Leadership Group, a nonprofit coalition working to curb greenhouse gas emissions in cities worldwide. He's leaving July 1.

"Not under a cloud, I hope," Alpert joked in an interview on Thursday, hours after he'd informed the mayor's office staff of his decision. Hales has known about the departure since last week, and is supportive, Alpert says..

The departure means Hales—like Sam Adams before him—will have at least three chiefs of staff during his four-year term. Former chief Gail Shibley left last July for a position with the state. Tera Pierce, Alpert's deputy, will succeed him for Hales' final six months in office.

But Alpert's departure has the potential to be more acutely felt than Shibley's. No member of Hales' staff has haunted City Hall quite as thoroughly (we named Alpert the most underrated City Hall staffer not long ago. It's difficult to find people who'll speak ill of him in that building, even if they have beefs with how the office conducts business.)

More importantly, Alpert has been the point person for a homelessness strategy that has earned Hales the ire of business interests and some neighborhood organizations, even while cheered by advocates and watched closely by other cities.

That strategy—which includes allowing people to sleep on the sidewalk and erect tents on some lots, as well as providing for more organized homeless camps—is still seriously in flux. Not only that, but Mayor-elect Ted Wheeler has been promising to undo at least part of it when he takes office.

Alpert vows that his departure doesn't mean Hales is abandoning the controversial effort.

"I wouldn't leave if I didn't feel like our team has this," he said. "They're moving forward. We're not giving up on any of the big ideas."

Central to Alpert's view of the homelessness issue—and therefore Hales'—is the fact that the city has no options for thousands of people who are without shelter on a nightly basis. Given that, he says, it's wrong for Portland to outlaw camping in every form. And with recent hints that the US Department of Justice agrees, Alpert says federal court opinion is headed toward the same conclusion.

"Nobody other than our office has put forward a plan about: What do we do tonight?" he says. "I will not stop singing that song."

Alpert's relatively short time as chief of staff has been eventful to say the least. In October, Hales shocked the city by announcing he wouldn't run for a second term. That followed a break with business interests, who'd been quietly encouraging Wheeler to pose a stern challenge.

The months since that announcement have been Hales' most dynamic in office—largely due to the homelessness policy and the declaration of a housing state of emergency (which kicked in a few weeks before Hales said he wouldn't run).

Alpert, one of three remaining staffers who've been with Hales since he took office in January 2013, makes no secret of the fact he's "burned out." But he insists he'd have stayed on with Hales if his new employers hadn't asked him to start sooner. Still he's giving himself a month-long break between gigs—he starts August 8.

"I wanted my deputy to have meaningful time as chief," he says of Pierce. "There is stuff for her to do as chief before we leave that’s big."

Besides, "I've been working for a really long time without a break."

Alpert will remain in Portland, making more money and working on limiting inequities in how global climate change is felt. He says he will not have any business before City Council.