March 5, 2025 Story by: Editor
With Republicans now in control of Washington, their focus has shifted to a progressive stronghold in Pennsylvania.
Prominent donors backing President Donald Trump are heavily investing in the Pittsburgh mayoral race, aiming to unseat current Mayor Ed Gainey.
Three months before the primary, GOP-affiliated donors have already contributed over $130,000 to O’Connor’s campaign, making up more than 20% of his January fundraising total. According to campaign finance reports from January, at least five major Republican and Trump donors have each given the maximum contribution to O’Connor’s campaign, helping him amass $464,000—far surpassing Gainey’s $23,600.
Gainey has taken strong progressive positions on issues such as housing and immigration, whereas O’Connor is perceived by conservative donors as more neutral, according to Tanisha Long, an Allegheny County political director for Straight Ahead, a criminal justice initiative under the Abolitionist Law Center and a supporter of Gainey.
“A lot of the Republicans,” Long said of the donors, “are running with the fact that Corey doesn’t really take hard stances on things.”
She added that while O’Connor avoids directly aligning with Republican donors, he does not reject their financial backing: “He won’t outright embrace those people, but he will very happily accept checks.”
In Pittsburgh’s political landscape—where the Republican Party is relatively weak—it is not uncommon for GOP donors to contribute to Democratic candidates. However, Long noted that such a significant flow of Republican money into a Democratic primary is unusual for the city.
Democratic City Councilmember Barb Warwick, who represents O’Connor’s former council district and supports Gainey, expressed concern over the GOP’s involvement in the race. She argued that Trump’s approach—favoring developers and tech elites—has already shaped Pittsburgh’s right-wing politics.
“It makes sense that they are putting money toward getting rid of him,” Warwick said, referring to the donors’ efforts against Gainey. “It doesn’t surprise me that the same folks who are trying to overstep what’s good for regular people on the ground at the national level are also trying to push aside a mayor who is really focused on what’s good for the people living here in Pittsburgh today.”
Meanwhile, O’Connor’s campaign has defended his record, asserting that he stands for progressive values.
“Corey has delivered for workers by challenging wealthy corporate interests, stood alongside community members against developers, and took a stand against the powerful gun lobby,” said his campaign spokesperson, Ben Forstate. “The fights that he has undertaken for Pittsburgh residents show that he cannot and will not be bought by anyone.”
Upcoming campaign finance reports will shed further light on fundraising trends. O’Connor has so far outperformed Gainey in both small and large donations. His campaign reported more than 250 contributions over $250, totaling over $450,000, whereas Gainey’s campaign reported only 15 such contributions, adding up to $14,725.
Forstate emphasized the broad base of O’Connor’s small-dollar donors:
“The fact that we’ve raised more than our opponent in small contributions from more individual small-dollar donors,” Forstate said, “shows Pittsburghers from all walks of life—whether they’re laborers, teachers, service workers, paramedics, or retirees—are behind Corey.”
Trump Allies and GOP Donors Enter the Race
Beyond financial contributions, Trump-aligned political operatives have also engaged with O’Connor’s campaign.
Kent Gates, a Trump consultant and pollster whose firm has received a six-figure payment from Trump’s 2024 campaign, recently attended an event with O’Connor. The event—a roundtable with local business leaders—was organized with assistance from GOP strategist Jeff Kendall, a known ally of billionaire and Republican mega-donor Jeffrey Yass. (Neither Gates nor Kendall responded to requests for comment.)
Forstate stated that O’Connor’s campaign was unaware of the organizers’ political affiliations and did not seek donations at the event.
“He did not request donations, and this was not an event planned, organized, or produced by the O’Connor campaign,” Forstate said. “We’ve taken zero dollars from Gates or Kendall. We were not aware that the event was organized by those individuals.”
Still, some prominent Trump donors have made contributions. Pennsylvania mining firm owner Clifford Forrest, who donated $1 million to Trump’s 2016 inaugural committee, contributed $3,300 to O’Connor’s campaign in January. (Forrest did not respond to a request for comment.)
O’Connor’s team pointed out that Gainey has also accepted donations from Republicans, particularly during his 2021 general election campaign.
“Our campaign took our lead on fundraising from the mayor,” Forstate said in a statement to The Intercept, referencing a past contribution from Forrest to Gainey in 2021. “Over the last four years, Mayor Gainey took over $82,000 from Trump and GOP donors.”
During the 2021 election cycle, Gainey raised $55,600—about 5% of his total donations—from Trump donors and registered Republicans. However, many of these Republican donors are regular contributors to Democratic candidates and have no known history of funding GOP campaigns. Gainey also accepted $5,000 from Clifford Forrest and his wife in 2021. His campaign recently refunded that donation, calling it an oversight.
Nonetheless, O’Connor’s January fundraising from GOP donors—accounting for over 20% of his total haul—far exceeds the total Republican donations Gainey received in the past four years.
Among the high-profile GOP donors backing O’Connor is Herb Shear, a billionaire who has given hundreds of thousands of dollars to pro-Trump organizations. He contributed the maximum allowable amount to O’Connor’s campaign last month. Other major Republican donors who also maxed out their contributions include Kent McElhattan, John Staley IV, and Thomas Grealish. O’Connor’s campaign did return one GOP donation, though none of the Republican donors responded to requests for comment.
A Progressive Battle in Pittsburgh
Pittsburgh has become a battleground for progressive politics, with Republican donors seeking to counter the movement’s influence.
Gainey has played a key role in the rise of progressive leadership in Western Pennsylvania, even as broader Democratic support has waned. He has been an outspoken critic of Trump’s immigration policies and has vowed that Pittsburgh will remain a welcoming city for immigrants.
In January, Gainey reaffirmed his opposition to Immigration and Customs Enforcement (ICE) operations, stating that his administration would not cooperate with ICE and that Pittsburgh, a city built by immigrants, would “always be welcoming of everybody.”
His victory in 2021 helped pave the way for other progressive leaders, including Rep. Summer Lee (D-Pa.) and Allegheny County Executive Sara Innamorato, who won her seat in 2023.
O’Connor, while also part of the city’s progressive movement, has faced scrutiny over his campaign’s financial ties. The son of former Pittsburgh Mayor Bob O’Connor, he served as a city council member from 2012 to 2022 before being appointed Allegheny County Controller by former Governor Tom Wolf.
Elected to a full term as controller in 2023, O’Connor has focused on criminal justice reform and transparency, particularly in relation to the county jail’s impact on local families. He also declined an invitation from the American Israel Public Affairs Committee (AIPAC) to challenge Summer Lee in Congress, according to The Intercept.
As the Pittsburgh mayoral race intensifies, the growing influence of Republican donors remains a key point of contention, with both candidates facing scrutiny over their financial backers.
Source: The Intercept
