Ted Wheeler's Second Act

In his second term, Portland's mayor tacks to the center in an attempt to save his city

Since choking on tear gas and nearly losing his job in 2020, Portland Mayor Ted Wheeler has broken with progressive orthodoxy in an attempt to restore order to his city. (Photo courtesy New York Times).

The night of July 22, 2020, found Portland, Oregon mayor Ted Wheeler choking on tear gas in a crowd of protesters outside a federal courthouse in downtown Portland. He had come to show solidarity with the protesters in their standoff with federal law enforcement officers, but Wheeler was mostly on the receiving end of insults. They asked how he liked being tear gassed, and called him “Tear Gas Teddie” on account of Portland police having used tear gas on them previously. Wheeler observed, “A lot of these people hate my guts.”

That they did. On his birthday in August 2020, a group of 200 vandals gathered at the building housing Wheeler’s apartment, sprayed graffiti, broke windows and threw a burning newspaper into the ground floor of the structure. Wheeler moved out later that week, apologizing to his neighbors for the damage to their homes.

It’s not as though Wheeler had governed Portland, either before or during the protests and riots that plagued the city for months, like a law and order Republican. He had in fact indulged protesters and their anti-police rhetoric, speaking, for instance, about what he saw as a “transformational moment” at a protest at which a “Disband the PPB (Portland Police Bureau)” banner was displayed. In June 2020, Wheeler voted to defund the Portland police to the tune of $15 million, and disband a unit dedicated to reducing gun violence. Many progressive politicians played footsie with defunding the police in 2020. Wheeler actually did it.

Those anti-police bona fides earned Wheeler not only the aforementioned personal attacks from anti-police activists and anarchists but also a serious opponent in his 2020 re-election campaign. Sarah Iannarone, who described herself as a communist, refused to condemn violence and property damage in support of left-wing causes like that which was consuming Portland on a nightly basis.

In part because Portland does not lack for espoused communists blessed by the fruits of capitalism, Iannarone outraised Wheeler through the mayor’s summer of discontent. As the election approached some polls showed her beating the incumbent, one by 11 points. Faced with the prospect of a mayor who just might welcome even more chaos, the Portland business community swung into action, leading an independent expenditure campaign that tipped the contest in Wheeler’s favor. When all the votes were counted, Wheeler bested Iannarone by only 5.5%, with 13% of voters supporting a write-in candidate. A solid majority of Portland voters didn’t want Wheeler to continue to be mayor, but he had survived.

Wheeler entered his second term determined to govern differently. Some combination of the heckling and the tear gassing and the growing violent crime and the rampant homelessness plaguing Portland and, perhaps most importantly, the nearly losing drew Wheeler to the center (by Portland standards, to the right) on crime, policing and homelessness. In his second term, and in marked contrast to his first, Wheeler has shown a surprising willingness to butcher the sacred cows of proper-thinking Rose City progressives. Consider:

Echoing New York Mayor Eric Adams, Wheeler wants the state to make it easier to involuntarily commit the mentally ill, who make up a large percentage of the homeless population.

Wheeler is pushing a proposal to ban outdoor homeless camping, a bold move in a progressive west coast city. Although the outright camping ban is not yet in place, and faces strong opposition from partner agencies, Wheeler is using existing legal authority to conduct massive and frequent sweeps of homeless camps in Portland’s Old Town and Central Eastside industrial areas, home to some of the city’s largest concentrations of homeless camps.

In an attempt to revitalize the downtown core rocked by protests, riots and homelessness, Wheeler is forcing city employees to work at least half-time in person (they have mostly worked remotely since the COVID outbreak). He has issued an executive order to clean up trash and graffiti to make downtown more appealing to suburban (privileged in 2020 parlance) shoppers, diners and workers.

In a recent appearance on regional conservative radio host Lars Larson’s show, Wheeler celebrated Portland hiring more police officers, working with the FBI to address the city’s spiraling murder crisis, and generally downplayed his and Portland’s adventure in defunding the police. Wheeler now supports putting police school resource officers back in Portland public schools, after the city yanked them out in 2020.

The reforms favored by Wheeler, and more, are needed to stabilize Portland, stop the flight of small businesses from the city, and revitalize the swaths of the city gutted by the turmoil of recent years. Even if he accomplished all of them, Portland would continue to rank, nationally, as a very, very progressive city. But Wheeler now wants Portland governed like the very progressive city it was a decade ago, not the anarchical city it has been trending toward, at times and in places, since 2020.

Wheeler’s second-term rebirth as a relative moderate has made him into the most moderate high-profile elected Democrat in the State of Oregon, and it’s not even close. Wheeler, mayor of Oregon’s biggest, bluest city, is well to the right of newly-elected governor Tina Kotek, for example, on crime, policing, homelessness and a host of other issues.

Kotek’s constituency includes not only Portland but the rest of the state, all of which is more conservative, in some cases much more conservative, than Portland. Wheeler has clearly bet his political future on the return of a semblance of order to Portland via traditional methods like stepped up policing; Kotek prefers the softer harm reduction and social spending approach that many Oregonians blame for the state’s drug, homelessness and crime crises.

The conflict between the approaches favored by Wheeler and Kotek is sure to create fireworks for the next two years, and possibly beyond. If Wheeler succeeds in turning Portland around and wins a third term in 2024, a showdown between the relative moderate mayor and the dyed-in-the-wool progressive incumbent would make for an entertaining Democratic gubernatorial primary in 2026.

More broadly, Wheeler is testing the willingness of progressive urban voters to scrap some of the more extravagant plays in their 2020-2021 game-plan in exchange for order, cleanliness and safety. Wheeler’s governance asks, can a really progressive big city govern itself in this immediate post-COVID, post-George Floyd world? The answer to that question will have implications for big, progressive cities throughout the country.