Last fall, Pittsburgh’s Democratic mayor, Ed Gainey, sparked an uproar after he signed onto an insensitively worded joint statement addressing the one-year anniversary of Hamas’ Oct. 7, 2023, terror attacks, drawing widespread backlash from Jewish community leaders and prominent elected officials.

The statement, which he had written along with Rep. Summer Lee (D-PA) and Allegheny County Executive Sara Innamorato, faced accusations of equivocating over the attacks while blaming Israel for the massacre and the widening war in the Middle East. Most notably, it made no mention of Hamas. 

Mainstream Jewish leaders in Pittsburgh weren’t alone in finding the statement offensive. Days after its release, Gainey’s campaign treasurer, Jonathan Mayo, wrote an anguished message to the mayor, as well as Lee and Innamorato, conveying his profound disappointment with the sentiments they expressed.

“I felt it was poorly worded, hastily constructed, ill-timed and tone deaf in terms of how it would land with the Jewish community,” Mayo, who is Jewish, wrote in an Oct. 22, 2024, email recently obtained by Jewish Insider. “What upsets me the most is the fact that you have friends and allies in the Jewish community who have told you time and time again that they are willing to help in any way,” he said in the lengthy message, “but that you don’t reach out to.”

Even as he clarified that they still had his support, Mayo said he was “heartbroken by what seems like a consistent lack of effort in using the guidance that’s been offered repeatedly,” suggesting that the elected officials had failed to “fully” understand “communal trauma and pain” in response to the Hamas attacks.

The unvarnished reaction to Gainey’s statement from a dependable ally encapsulated the depth of dissatisfaction within the wider Jewish community over his outreach and engagement on key issues, as he seeks reelection in the May 20 primary against a formidable challenger who has said that Pittsburgh voters “deserve better” than the imperiled first-term incumbent.

In a comment shared by Gainey’s campaign on Wednesday, Mayo said he had “struggled with” parts of the statement, “but one of our mayor’s strengths has always been that he leads with compassion and is open to different viewpoints.” Mayo said that he and Gainey “have discussed the statement specifically and it is due to” the mayor’s “willingness to listen and learn that I am proud to stand with him as he shows up time and again for all of Pittsburgh’s disparate communities, including our Jewish community.” 

Before the email was sent, the mayor had doubled down on his statement in a lengthy comment to JI and refused to acknowledge it had caused offense.

The mayoral race has drawn national attention in recent weeks as Gainey’s opponent, Corey O’Connor, the Allegheny County controller who launched his bid in December, has taken a wide lead in polling, won crucial endorsements and significantly outpaced the mayor in fundraising. In the latest blow to Gainey’s campaign, he narrowly lost the endorsement of the Allegheny County Democratic Committee this week, in an upset that O’Connor celebrated as “a sign” that “the people around this city want a change.”

“Gainey’s behind in a big way,” said Mike Mikus, a Democratic strategist in Pittsburgh who is leading the independent spending group that commissioned the poll, called Common Sense Change. “I wouldn’t quite say his campaign is dead on arrival, but he is in deep, deep trouble. I’ve never seen an incumbent mayor in this bad a shape politically heading into an election.”

Meanwhile, a poll commissioned by an independent expenditure group supporting O’Connor, which has not previously been reported, showed the controller at 55%, with a 23-point lead over Gainey, who claimed just 32% among likely Democratic primary voters in Pittsburgh. Fourteen percent of voters were still undecided.

The mayor also lagged behind O’Connor in his favorability ratings, according to a polling memo shared with JI on Wednesday. Gainey was rated unfavorably by 47% of voters and favorably by 45% — while O’Connor notched 61% favorability and was seen negatively by just 8% of respondents, the poll showed. 

The poll, which surveyed 400 likely Democratic primary voters in the city, was conducted by Global Strategy Group between Jan. 27-30. Another recent poll has O’Connor holding a 12-point lead over Gainey, who has ramped up his attacks in recent days as the primary draws closer.

“Gainey’s behind in a big way,” said Mike Mikus, a Democratic strategist in Pittsburgh who is leading the independent spending group that commissioned the poll, called Common Sense Change. “I wouldn’t quite say his campaign is dead on arrival, but he is in deep, deep trouble. I’ve never seen an incumbent mayor in this bad a shape politically heading into an election.”

Mikus said that it would be overly simplistic to cast the race as a face-off between warring moderate and progressive wings of the party. The primary, he said, is more a referendum on Gainey’s leadership as the city has failed to provide basic government services including snow plows while struggling with a police shortage, homelessness and affordable housing challenges, all amid frequent staffing turnover in his administration.

Still, Gainey’s embattled reelection campaign fits into a broader national trend in which progressive big-city mayors have garnered backlash over policies and rhetoric increasingly seen as politically toxic in the second Trump era. 

“We have asked time and time again for him to to be our ally and to stand up for us — and unfortunately, we have been met with great disappointment,” said Jeremy Kazzaz, executive director of a local Jewish advocacy group called the Beacon Coalition, whose political arm has donated to O’Connor’s campaign. 

In Oakland and San Francisco, both mayors were recently ousted from office, while Boston’s mayor, Michelle Wu, is facing a new primary threat from moderate challenger Josh Kraft. In Chicago, Mayor Brandon Johnson is weathering a series of controversies as his approval ratings have plummeted. In New York City, former Gov. Andrew Cuomo is now leading the mayoral race as he mounts a comeback campaign in a primary field populated by left-wing rivals largely failing to gain traction.

In Pittsburgh, meanwhile, the Jewish community, which represents a sizable and politically engaged segment of the Democratic electorate, could play a decisive role in shaping the outcome of the primary, experts say, especially as Gainey has faced growing frustration among Jewish leaders over a continued lack of outreach amid an uptick in antisemitic incidents and anti-Israel activity in the wake of the Hamas attacks.

“We have asked time and time again for him to to be our ally and to stand up for us — and unfortunately, we have been met with great disappointment,” said Jeremy Kazzaz, executive director of a local Jewish advocacy group called the Beacon Coalition, whose political arm has donated to O’Connor’s campaign. 

Most recently, Kazzaz told JI, Jewish leaders in Pittsburgh had lobbied for the mayor to oppose a controversial effort by far-left activists to bring an Israel boycott and divestment referendum to voters — less than a year after a first failed attempt to put the issue on the ballot. 

While the second proposed ballot measure was also withdrawn last week after a court challenge, Kazzaz said that it was not because Gainey had been willing to step in. “The mayor decided not to stand with the Jewish community and instead just stand back and let these things take their initial course, which put a gigantic burden on the Jewish community,” he said in a recent interview.

In a statement to JI in late February, Gainey said that he had “serious concerns” about the proposed effort’s impact on the city government and its “ability to conduct basic functions,” while adding that he was “also personally concerned by the alarm that this referendum is causing in parts of our Jewish community.”

“That being said, I also acknowledge the apparent strength of feeling among our residents who want to intervene on behalf of Palestinians, and believe that most Pittsburghers share this sentiment, alongside a commitment to combatting antisemitism,” Gainey said in his statement.

To Kazzaz and other Jewish activists in Pittsburgh, however, Gainey’s inaction was part of a deeper issue. “It is that sort of lack of allyship in that case, or in the various instances where elected officials — including this mayor — have failed to really call out acts of antisemitism in the moment by name, that has been amping up a general dynamic making the Jewish community in Pittsburgh, I think, generally uncomfortable,” Kazzaz explained.

Experts say that Gainey will need to perform well in Pittsburgh’s 14th Ward, which includes the heavily Jewish neighborhood of Squirrel Hill, if he hopes to prevail in the primary, which is now 10 weeks away. “Ed doesn’t have much room for error there, and if he goes backward he’s in a load of trouble,” said one Democratic strategist who is not working for either of the campaigns. 

“Being part of that community and understanding what the issues are and what their thoughts are on protecting the State of Israel and being a good ally for the United States, I see that every day,” Corey O’Connor said, while vowing to fight antisemitism he called “rampant not only in” Pittsburgh but in “other cities across the country.”

But as many Jewish community members have grown disaffected with his leadership, Gainey, who himself unseated a Democratic incumbent in 2021, is now facing political headwinds that could make a difference in the race.

For his part, O’Connor has long-standing ties to Squirrel Hill, where he was born and raised. He has also represented the neighborhood as a former city councilman, and he boasts strong relationships with Jewish leaders in that precinct and across the city.

In an interview with JI on Wednesday, O’Connor said his Jewish neighbors in Squirrel Hill instilled in him a commitment to fighting antisemitism and standing up for Israel that he continues to value. 

“Being part of that community and understanding what the issues are and what their thoughts are on protecting the State of Israel and being a good ally for the United States, I see that every day,” he said, while vowing to fight antisemitism he called “rampant not only in” Pittsburgh but in “other cities across the country.”

“For me, it’s going to be as I’ve always done,” he added. “I’ll be a fighter for the Jewish community and every community in Pittsburgh. That’s the job.”