Can a progressive mayor survive in Pittsburgh?

Pittsburgh has not seen the sort of capital flight or high-profile crime surge that weakened progressive mayors in other cities since 2020. The city’s population is stable, and its homicide rate fell last year, despite an ongoing struggle to find a permanent police chief that’s been a source of bad headlines for Gainey.

But in very different places, the same story has played out: Voters who demanded police reform and fair housing have soured quickly on progressive mayors and questioned their competence.

In St. Louis, voters tossed out Mayor Tishaura Jones, who’d won her single term as a champion of the Black Lives Matter movement. In Oakland, scandal-plagued mayor Sheng Thao was recalled on the same day that a reform prosecutor was recalled; former Rep. Barbara Lee, a progressive who entered the replacement election as a heavy favorite, appears to have lost it. If the final count of ranked-choice voters holds up, the mayor of one of America’s most liberal cities will be Loren Taylor, a former city council member who ran on hiring more police and using drones to pursue more criminals.

Gainey has a unique challenge in Pittsburgh, where he and other Democrats have refused to speak with the city’s biggest newspaper, the Post-Gazette, until it settles a labor dispute that began early in his term. “I’m the one that’s been their lightning rod,” Gainey said, pointing to the paper’s steadily negative coverage.

He’s also lost some Democratic organization and union endorsements to O’Connor, and Democrats who want change say they will simply get better leadership — still progressive — if he’s gone. “There’s a continuing sense of frustration about opportunity,” said DeWitt Walton, an Allegheny County Council member who supports the challenger. “We’re faced with increasing downward economic pressures and he hasn’t provided some kind of leadership.”

The mayor’s progressive allies say that the city’s old guard and the developers who typically hold influence on urban politics are trying to wrestle back control. They do not say that everything has gone right under Gainey; they say that he’s been lied about, and not given the time and space to succeed.

“We’re seeing an attack on progressives. We’re seeing an attack on black politics,” said Rep. Summer Lee. “It’s important to note that these are the very same people who have had control over our government for decades upon decades upon decades, who are now trying to convince you that progressives being in office for two years have somehow done damage. They’re saying: Listen, we gave you two years, and you weren’t able to undo the damage that we’ve done generationally. But that’s just not the narrative that’s getting out.”

To counter that, Gainey has worked to nationalize the race, portraying O’Connor as a “MAGA money” candidate, based on donations from people who’ve also given to Republicans. “My opponent knows that these are lies,” O’Connor shot back at Thursday’s debate. “He’s known me for 30 years.”

The two men haven’t disagreed on opposing the Trump administration, at every possible level. Both say they would refuse to cooperate with ICE; both oppose the new president’s orders on gender and race that have already forced policy reversals on Pittsburgh hospitals. On Wednesday, Gainey joined activists at an SEIU office downtown for a town hall on how he was resisting the administration.

“I’m not concerned about what they do in DC,” Gainey told his audience. “I’m concerned that they understand that if you want to do business with me, that you have to adhere to the anti-discrimination policies that we put in place.” It was ironic, he added, that a president who had questioned Barack Obama’s citizenship “put a man from South Africa” into a position where he can “bring terror on America.”

I heard a common goal from Gainey and O’Connor this week, in between the disagreements. Both wanted Pittsburgh to thrive in a way that changed how people looked at the city, and at progressive governance. Both wanted to show that Democrats could fight crime, build housing, and make cities livable in a way that refuted MAGA and Republican attacks.

Gainey said that project was underway, and he acknowledged that there had been a backlash to the progressive energy that swept people like him and Lee into office. That was visible as early as 2023, when Sara Innamorato, who like Lee had beaten an incumbent state legislator with an unapologetically democratic socialist campaign, barely won the race for Allegheny County executive. (During the campaign, she rejected the “democratic socialist” label.)

“I think that justice is always going to be at the forefront of how we advance society,” said Gainey. “You will always have the contrast to that of people of power who are comfortable with the way society is, because it’s in their best interest. Sometimes the power can feel too heavy, and people may weary for a moment. But I’ve never seen a people stay down when oppression is rising.”

O’Connor saw a different way to the goal of Democratic credibility: Getting rid of Gainey, adding more public safety resources, and spending money more wisely. “You look at how they managed the COVID relief money,” he said. “We’ve seen other cities buy new ambulances — which we need, they’re breaking down. Buy new plow trucks, update your fleet, update your technology. Instead, we went out and hired 100 employees, who next year we can’t pay.”

He was talking about a new administration in DC that saw progressive governance as a disaster, and would be working to undermine and defund it. Mayors elected in Trump’s first term could mobilize against him; mayors elected under Biden could talk about the resources they might get from a friendly administration. This is new territory and no incumbent has crossed it yet.