A Trump megadonor leans into a tight swing-state Democratic primary

Independent

03-03-2025

Republican money is flowing in a Democratic primary election in Pittsburgh, even if conservative values aren't.
MAGA Republicans would be hard-pressed to find something to love in the Pittsburgh mayoral race. With the state having awarded Donald Trump its electoral votes in 2024, Pittsburgh remains a stubbornly blue holdout, standing defiantly against the state's reddening suburbs and rural districts. A Democrat is widely expected to win — one lone Trump supporter is battling an openly gay Republican for the GOP nomination, having already run and lost the race before.
So why is Pennsylvania's richest man, who was one of the biggest by-dollar supporters of the GOP in the last election cycle, putting his money behind the primary opponent of Pittsburgh's embattled Democratic mayor, Ed Gainey?
For starters, he's always involved.
Jeffrey Yass is quickly becoming the most important name in Pennsylvania politics, even without running for office himself. The billionaire businessman doubled his net worth with an investment in TikTok 's parent company in 2024, but even before that windfall had been bankrolling politicians in a notable number of races across the state — particularly in Allegheny County, home to the state's second-largest city.
His involvement has infuriated Democrats in the region for years. For starters, Yass does not live there: He resides in Lower Merion Township, a mere 4-hour drive from the center of Pennsylvania steel country.
And then there's the obvious issue — his Republican leanings. Yass was a top contributor to GOP candidates and causes in the last election cycle, shelling out around $100 million to various groups and Republicans around the country. That includes Donald Trump, in whom he found an ally willing to reverse a ban on TikTok weakly pursued by the Biden administration (but a ban that previously had the support of many Republicans).
'Jeffrey Yass is the richest man in Pennsylvania, and he's funded one out of every three of our legislators here in Pennsylvania since 2017 in an effort to push his agenda,' Mary Collier, developer of the 'Yass Tracker' told a local news outlet in January. Her tool tracks the spread of his money across state politics.
On Monday, Gainey, a progressive and Pittsburgh's first Black mayor, is set to open up a new line of attack: His opponent, Allegheny County Controller Corey O'Connor, is the latest recipient of Yass's largesse — and perhaps one more cog in the effort to reshape the state's politics. His team, at a press conference, is set to frame the race as a battle against this latest invasion of Trump-aligned GOP money.
Filings with the state Department of Elections reviewed by The Independent indicate that O'Connor has taken donations this cycle from several major Republican donors who've funded GOP candidates like Trump — and bankrolled any challenge to candidates aligned with the progressive wing of the Democratic Party.
One of those donors is Kent McElhattan, venture capitalist and founder of the nonprofit McElhattan Foundation, who was a top supporter of Dave McCormick in his successful bid to oust incumbent Democratic Pennsylvania Senator Bob Casey last year. Another is Herb Shear — yet another venture capitalist — who gave hundreds of thousands in support of Trump's 2024 election and nearly $50,000 to a PAC supporting a Democrat, Bhavini Patel, who was ultimately defeated in the Democratic primary for Pennsylvania's 12th Congressional District, the same year. Patel's campaign was described at one point as representing an 'onslaught of far-right cash' against incumbent Summer Lee, a congresswoman and member of 'The Squad.'
An email provided to The Independent also indicated that O'Connor was due to meet in February with two GOP operatives closely tied to Yass, Jeff Kendall and Kent Gates. The email suggests that Gates, an operative with a national GOP consulting firm, was to present a strategy aimed at unseating the incumbent Mayor Gainey at the meeting.
A spokesperson for O'Connor's campaign told The Guardian that the O'Connor campaign 'had no involvement in the planning' of that event, but did not deny that O'Connor attended. They also argued that Gainey has been the recipient of money from GOP-aligned donors in past cycles.
'Corey spoke about his record of progressive reform and his plans to make housing more affordable, expanding before and after school programming, and reopening [recreation] centers,' a spokesperson told The Guardian.
'This is the same stump speech that he has shared with hundreds of residents and dozens of community organizations across Pittsburgh. The campaign did not know who would be in attendance in advance.'
One Pennsylvania-based Democratic operative described the group to The Independent as a network of wealthy conservatives who 'meddle in Democratic primaries to replace people-powered leaders who've stood up to Trump and won with corporate-bought politicians willing to bend to MAGA billionaires' and their right wing agenda.'
The influx of money tied to the GOP is making a clear impact on the Pittsburgh mayoral primary: Lee and another target of Yass's operatives, County Executive Sara Innamorato, have lined up in Gainey's camp — while O'Connor enjoyed his best fundraising month of the race in January, and outraised the incumbent 20-to-1.
'We knew going in that we (weren't) going to have the big donors,' Gainey told a news outlet last month.
He added to NPR affiliate WESA: '"The reality is — when your buddies are corporate developers, union busters, and hospital CEOs, you're going to raise a lot more money than a campaign fighting for nurses, teachers, and firefighters. I was elected after being outraised four to one because of the people-powered coalition that has only grown as I've delivered for the regular people of this city as Mayor — and we're ready to do it all over again.'
A few factors do differentiate the two Democrats politically. O'Connor supports funding more cops on the street, while Gainey has touted support for alternative methods, including putting social workers on some police calls. In 2024, a number of Gainey's staffers supported a ballot measure that would have called on the city to divest from the Israeli government. O'Connor's allies have attacked progressives as uninterested in governing.
'There is no vision coming off of Grant Street anymore,' O'Connor said at his campaign launch in December. 'Instead, as I look around, I see a mayor and administration that's managing decline instead of working to grow Pittsburgh.'
But even if he unseated Gainey for the Democratic nomination, O'Connor would be no ally of Donald Trump in office. And so it's not totally clear why else MAGAworld would take a strong interest in O'Connor, who like Gainey repeated a pledge to resist ICE detention efforts in the city at a candidate forum several weeks ago, if not to merely punish progressives.
In recent weeks, O'Connor has picked up an endorsement from the Young Democrats of Allegheny County, which backed his opponent in 2021, as well as a sizable chunk of union support. Gainey, meanwhile, has the support of the thousands-strong United Steelworkers and a slate of other left-leaning organizations, and retains close ties to the SEIU, which supported his last run.
Should O'Connor win, this primary election could end up encouraging Democrats to take another look at not just the Democratic Party itself but its primary election — and the growing willingness of conservatives to use them as opportunities to put a thumb on the scale.