Gainey Should Be Prepared to Lose PGH Mayoral Primary
Pittsburgh Mayor Ed Gainey’s team spent the winter insisting that his re-election was a foregone conclusion, waving around an internal Upswing poll that put him seven points up on Allegheny County controller Corey O’Connor among likely Democratic voters in the upcoming May 20 primary – 49-42, if you believe house numbers commissioned by an incumbent for whom handing out free recycling bins counts as “transformative governance.”
Inside his bubble that poll was scripture. Outside of it, the story was very different. First came an Upswing survey released to allies of O’Connor that showed the challenger twelve points ahead, 50-38, and identified housing, not presidential politics, as the race’s driver.
Then the Allegheny County Democratic Committee tallied its endorsement ballots and, after a recount, confirmed O’Connor on top again – a small-scale plebiscite that broke the illusion of Gainey’s inevitability. A mayor who once rode progressive enthusiasm to power was suddenly the establishment man begging for another turn at bat.
Follow the money and the picture sharpens. O’Connor raised almost as much in his first three weeks as Gainey did in the final six and a half months of 2024, hoovering up checks from developers, parking-garage kingpins and every East End retiree who still keeps a framed Bob O’Connor “Redd Up Pittsburgh” T-shirt in the basement. By early February the county controller had outraised the mayor for the month and was sitting on a cash-on-hand edge of roughly $311,000 to $268,000. Trades unions that backed Gainey four years ago crossed the street: the painters, the laborers, and the sheet-metal workers signed on with O’Connor. The United Steelworkers and Operating Engineers did endorse the mayor, but they and the other supporters that Gainey’s team could salvage simply might not be enough to reverse the mayor’s descent. When the checkbook class senses drift, it bails; the drift around Gainey now is unmistakable.
City-hall dysfunction has helped. Ambulances have broken down so often that the Bureau of Emergency Medical Services stopped keeping a formal count, the municipal equivalent of a teacher throwing up her hands and declaring that grades are colonialist. The 2025 operating budget, celebrated by Gainey as proof of “responsible austerity,” is an illusion built on spent federal COVID dollars and optimistic revenue projections that seem unlikely to pan out in the lean years that most see in the city’s future. Internal projections from city finance staff warn of red ink by 2026 unless overtime costs miraculously collapse and the pension fund doubles in value, two events less likely than the Pirates winning 90 games. Moody’s did move Pittsburgh’s bond outlook from stable to positive in January, but that was the ratings-agency version of a polite thank-you note; the accompanying documents cautioned about rising fixed costs and shrinking reserves as soon as federal relief cash dries up.
Despite “Keep Pittsburgh Home” emblazoned on the scant Gainey yard signs one sees throughout the city, the campaign he is running no longer feels like it belongs to Pittsburgh. KDKA’s Andy Sheehan documented how the Philadelphia branch of the Working Families Party has embedded paid operatives in Gainey’s headquarters, an arrangement the party calls “firewalled” even though its deputy political director appears regularly on Zoom strategy sessions with the mayor’s staff. A separate Post-Gazette investigation reported that Jake Pawlak, the city’s Office of Management and Budget director, uses a group chat to distribute talking points to nonprofit employees who are barred by law from electioneering on the clock; screenshots show a half-dozen city workers hitting the “like” button in unison every time Pawlak uploads a new meme. When Brandon McGinley wrote about that, he shared other juicy gossip, like the routine insults allegedly flung at O’Connor’s dead parents in that same chat.
Into that mess steps O’Connor, a man who lost both parents before the age of 35 and learned early that Pittsburgh adores nothing more than tragedy-tinged optimism. His father, the famously bouffant-haired long-time primary bridesmaid Bob, was finally sworn in as mayor in January 2006 and dead of brain cancer by that September. Corey O’Connor has never pretended to be the second coming, but he has spent ten unflashy years on council and two as controller proving he knows what bills get paid and when. In March, he stood in front of a condemned Knoxville row house and rattled off a list of overdue liabilities in the mayor’s office budget, promising to slash discretionary consultants and redirect savings to police recruitment bonuses.
Voters have noticed. On zoning, inclusionary mandates and the permitting backlog, O’Connor sounds like someone who paid to park in Lawrenceville recently; Gainey sounds like someone who hired an intern to do it. A separate WESA article chronicled the mayor’s efforts to nationalize the race, shoe-horning Trump into his messaging while implying that criticism of his policies was coded rhetoric aimed at a black officeholder. That line might play on MSNBC, but it tested poorly in this year’s Greenfield fish-fry queues, where even reliable Democrats were muttering that the city “looks rough” these days.
The donor split has sharpened class resentments in ways no consultant could script. Republican businessman J. Clifford Forrest wrote a five-figure check to O’Connor’s campaign, joined by fellow conservatives who once bankrolled countywide GOP slates, a fact Gainey surrogates recite as though the last Pittsburgh Democratic primary wasn’t heavily influenced by concerned Republicans with mountains of spare cash.
The progressive electoral machine that powered Gainey’s 2021 upset is sputtering. KDKA’s Andy Sheehan reported that the Working Families Party, OnePA and 1Hood “face their biggest challenge yet” in trying to re-elect the mayor after a string of earlier victories. Their ground game has been further undercut by those high-profile public defections from many of the building-trade unions that backed Gainey four years ago.
To make matters even worse, members of city council have been pressing for deeper oversight of Gainey’s spending priorities. Finance chair Erika Strassburger warned on WPXI that, with federal pandemic dollars drying up, the city must “come up with other revenue streams,” and she openly floated using violence-prevention money to buy police vehicles. City Controller Rachael Heisler has already begun a standing audit of the American Rescue Plan Trust Fund. Meanwhile, council allies of Corey O’Connor have highlighted long-stalled Parks & Recreation projects and a lingering p-card scandal; the Post-Gazette’s editorial board says that audit shows “what we still don’t know about park spending.”
Indeed, the Pittsburgh Parks Conservancy confirms that only four capital projects actually broke ground in 2024, despite $1.343 million set aside from the dedicated Parks Trust Fund. One conspicuous absence is the long-promised renovation of the McKinley Park grandstand. According to the city’s own EngagePGH project page, the plan is still stuck in “Design Development and Permitting,” with construction pushed off until at least 2026.
Corey O’Connor’s team has made easy work of seizing on those vulnerabilities. At a January press event in front of the long-shuttered Cowley Recreation Center, he blasted the administration for leaving ARPA park money “diverted to pet projects” while rec centers crumble. That critique dovetails with a PublicSource timeline showing years-long debate over ARPA transparency and repeated calls for controller audits.
Could seemingly sure loser Gainey pull it out? Of course. He is still the sitting mayor, still the beneficiary of a half-century of Democratic reflexes, still a veteran retail politician who can mine applause and votes from Homewood and the Hill District. But the tectonics look brutal. Low-turnout, off-year primaries reward cash and ground game; the challenger now has more of both. Polling swing, donor migration, union defections, and across-the-board fatigue with city-hall drift all tilt the chessboard toward change.
Four years ago, Pittsburgh sent Bill Peduto – who famously struggled to lift trash cans on an episode of Undercover Boss – packing for talking like an urbanist blogger and Uber fanboy while the bridges that those bike lanes and automated cars would pass over corroded beneath him. This year, it will likely do the same to a mayor who has treated political symbolism as a substitute for municipal service.
Perpetually grumpy Pittsburghers are slow to anger and about as fond of change as they are of crossing rivers, but they’re ruthless once roused. When they decide it is time for a new leader to take the reins, they seldom reverse course. Corey O’Connor is a competent custodian who is promising to keep the lights on, the sirens working, and the budget honest. In a city that just watched a police chief moonlight as an NCAA referee even as it drowns in blue recycling bins, that promise is more than enough. To protect his own gains while he’s still holding high office, Ed Gainey should start updating his résumé.