Pittsburgh Loses Gainey. Will O'Connor Honor His Promises?
Corey O'Connor's victory over Ed Gainey on Tuesday was arguably the most decisive primary upset of my four-decade lifetime, a triumph so unequivocal that it matters even more than the breathless election-night coverage suggested. When Gainey knocked off Bill Peduto four years ago, he needed current Republican nominee Tony Moreno in that race to split the anti-incumbent vote and claim a 46% plurality. O'Connor did what challengers almost never manage in Pittsburgh: he beat a sitting mayor straight-up, 53% to 47%.
The mathematics tell a story about coalition-building that the outgoing mayor never mastered. Gainey's 2021 win felt like a progressive wave cresting at exactly the right moment, carried by post-George Floyd energy and pandemic-era frustration with Peduto's technocratic fumbling. O'Connor's win looks like something more durable – a restoration of the boring competence that Pittsburgh voters usually prefer when they're not actively revolting against whoever happens to be in charge.
Unlike his famously bouffant-haired father Bob, who spent decades chasing the mayor's office only to die of brain cancer less than a year after finally claiming it, Corey O'Connor now has time to honor all those back-to-basics promises printed in that distinctive Mister Rogers font across hundreds of thousands of campaign fliers. His mandate is clearer than most incoming Pittsburgh mayors enjoy, and this isn't some ceremonial ribbon-cutting gig.
Pittsburgh operates under a "strong mayor" system, where the chief executive proposes budgets, signs legislation, and oversees daily operations while its City Council handles the legislative work. O'Connor spent a decade building relationships with all those council members, which means he won't waste months learning how to count votes.
The to-do list waiting on his desk would intimidate a more seasoned politician. Start with the police chief situation, which has devolved into a running joke that stopped being funny somewhere around the time Larry Scirotto was jetting off to referee college basketball games while homeless encampments expanded along the river trails. O'Connor campaigned on hiring a permanent chief, and he needs to find a hard case who will enforce broken-windows policing as aggressively as the budget allows – which immediately raises the question of what to do about the tent cities that keep sprouting on the North Side trails and remain scattered throughout other parts of the city.
The homeless problem intersects with Pittsburgh's broader housing crisis in ways that resist easy solutions. Some neighborhoods face an affordability crunch driven by carpetbaggers from Philadelphia and New York City who have discovered they can flee their high-expense cities by purchasing Lawrenceville row houses for less than the cost of a studio apartment back home. Meanwhile, other parts of the city remain cheap precisely because they're segregated, dangerous, or both, creating a dual market where gentrification and abandonment exist within walking distance of each other. O'Connor will need to thread that needle while somehow producing more affordable housing units than Gainey managed – a promise that sounds easier than it is when you're dealing with Pittsburgh's byzantine zoning and permitting processes.
School closures represent another inheritance that could define O'Connor's tenure. Pittsburgh Public Schools' latest appalling enrollment numbers show a student population of 18,650, down from 19,160 in 2021-22, with the state Department of Education predicting the district will lose another 5,800 students by 2031-32, bringing enrollment down to an almost-unimaginable 12,800 students. The proposed closure list includes solid buildings like Spring Hill K-5, where I cast my primary ballot for the Democratic nominee, along with 13 other schools slated for permanent closure. While no school closures will take effect for the 2025-2026 school year, district leaders have made clear that "change is essential" and they will continue pushing for closures in subsequent years. Some parents have smartly proposed that closed schools could serve as community hubs, teacher training centers, and spaces for community partners to host activities. But converting shuttered schools and creating an off-ramp for what's left of the area's student body requires the sort of creative thinking and sustained attention that Pittsburgh mayors often promise and rarely deliver.
The culture-war vestiges of the Gainey administration offer O'Connor a very quick win, assuming he has the sense to take it. Gainey championed initiatives that promoted diversity in local leadership positions, appointing what he called "the most diverse administration this city has ever seen," including the city's first black chief of staff, first trans communications director, first gay police chief, and first black woman to be chief of Emergency Medical Services. He forcefully repudiated GOP attacks on LGBTQ+ community members and announced that his administration wouldn’t work with ICE in response to Trump's immigration policies. While well-intentioned, much of this progressive messaging devolved into white liberals arguing with each other on social media while actual city services deteriorated and Trump increased his share of the Pennsylvania vote. O'Connor can dial back the more divisive elements without making a big show of it, freeing up political capital for fights that actually matter.
None of this will be simple, because O'Connor inherits a budget situation that his own campaign spent months describing as a looming disaster. The city's five-year financial plan projects the rainy-day fund shrinking from $208 million to $72 million by 2029, assuming everything goes perfectly and the local economy cooperates. Real estate tax revenue has been depressed by assessment changes and post-pandemic work-from-home trends that emptied downtown office buildings even as downtown green spaces swelled with homeless encampments. Federal Covid relief money that papered over structural problems during Gainey's tenure is running out, leaving O'Connor to choose between service cuts, tax increases, or both. It will take an iron will, but the smart move would involve converting that election-night majority into more tax money, persuading the rich voters who got him here to cough up a bit more so that the rest of us might find this place a bit less unlivable.
The political environment O'Connor enters differs markedly from the one that swept Gainey into office. Donald Trump is back in the White House promising massive federal spending cuts that could reshape everything from social services to infrastructure funding. The progressive energy that powered Gainey's upset has dissipated, replaced by voter concerns about basic municipal competence and public safety. Even most of the building trades unions that backed Gainey four years ago crossed over to O'Connor, including the painters, laborers, sheet metal workers, teamsters, steamfitters, plumbers, bricklayers, boilermakers, and ironworkers, with union leaders saying they were "frustrated with the lack of economic development in the city" and that "campaign promises fell to the wayside."
For O'Connor, this represents both opportunity and pressure. He ran as the steady alternative to Gainey's left-signaling symbolism, promising to fix a fleet of broken-down ambulances, hire a sufficient number of police officers to ensure 911 calls can be answered in a timely manner, and streamline the permitting process that developers complained had become impossibly bureaucratic. Those are achievable goals that don't require revolutionary thinking, just steady execution and attention to detail – qualities that O'Connor demonstrated during his decade on City Council and two years as county controller.
The bigger question is whether O'Connor possesses the political imagination to do more than simply restore the status quo that existed before Gainey's election. Pittsburgh's problems run deeper than municipal mismanagement, rooted in decades of population decline, industrial job losses, and the challenge of maintaining city services across neighborhoods with vastly different needs and resources. The easy stuff – moving past the p-card scandal, hiring a police chief who doesn't moonlight as a basketball referee, cleaning up the city’s flagging image instead of dispensing blue recycling bins – won't address the underlying structural issues related to the flight of the native-born population and the lack of an industrial base that has plagued even the best Pittsburgh mayors for generations.
Bob O'Connor's death robbed Pittsburgh of the chance to see whether his folksy charm and neighborhood focus could translate into transformative leadership. Corey gets that opportunity, with the advantage of lower expectations and fewer distractions. He's an area lifer with realistic goals, not nearly enough charm to succeed on the national scene, and deep roots – hence the controversial appropriation of that Mr. Rogers font for all his messaging – which means he might actually stick around long enough to implement sustained reforms instead of chasing the next electoral opportunity. That continuity could matter enormously in a city that has struggled with follow-through on long-term planning initiatives.
The stakes extend beyond Pittsburgh's city limits, as O'Connor's success or failure will influence how other post-industrial cities approach the balance between progressive aspirations and basic governance. If he can demonstrate that competent centrism still works in a place like Pittsburgh, it might provide a template for pragmatic leadership elsewhere. If he fails, it will reinforce the narrative that, outside of a handful of unicorn-like energy boomtowns such as Fargo and Bismark, most of the once-great American cities are stuck in a death spiral made worse by ineffective administration and periodic ideological purity crusades.
