In late spring of 2022, Rep. Jamaal Bowman (D-NY) reached out to a local Jewish leader in Westchester County to ask for an unusual favor as he prepared to defend his seat in an August primary against two Democratic challengers who were each gaining support from the district’s sizable Jewish community.

“Do you have pics of us?” Bowman texted the Jewish leader, with whom he had previously maintained a cordial if uneasy relationship, according to a screenshot of the message shared with Jewish Insider. “So I can show the world I’m friends with Jewish People.”

The Jewish leader, who described the exchange on the condition of anonymity to protect his privacy, did have at least one photo on hand from a Jewish community gathering in Bowman’s district months earlier at which the then-freshman Democrat had vowed to sign on to a House bill aimed at strengthening the Abraham Accords — a promise he fulfilled just a few days later.

But by the time Bowman sent his request to the Jewish leader in an apparent effort to counter mounting dissatisfaction with his record on Israel amid the campaign, the New York legislator had since reversed course and pulled his support for the bill aimed at further normalizing relations between Israel and its Arab neighbors — angering Jewish activists in the district who said they felt blindsided by his abrupt decision.

“I was uncomfortable,” the Jewish leader said of Bowman’s awkwardly worded text message two years ago. “I kind of joked around with him about it. I said, ‘Oh, I’m sure you guys have it. Don’t worry about it.’”

He didn’t share a photo — and Bowman, who defeated his challengers later that summer, never asked for one again, the Jewish leader told JI in a recent interview. “I was like, ‘I don’t want to be his court Jew,’” he explained of his thinking at the time of the exchange. “That wasn’t what I signed up for.”

Now that he is seeking a third term in a bitterly contested primary next Tuesday, Bowman has found himself in an increasingly uncomfortable position with Jewish voters as he has embraced a growing number of hostile positions toward Israel in the wake of Hamas’ Oct. 7 attacks — one of the top issues in his imperiled race for reelection.

More broadly across the Democratic primary electorate, polling has shown that Bowman’s extreme views on the Israel-Hamas war are not shared by a plurality of voters in his district, where he is facing a career-threatening challenge from Westchester County Executive George Latimer, a popular pro-Israel Democrat who is leading by double digits.

Bowman, who in January lost a key endorsement from the progressive advocacy group J Street over his approach to Israel, insists that he continues to draw significant backing from Jewish constituents, even as he has recently pledged to oppose funding for Israel’s Iron Dome missile-defense system and endorsed the Boycott, Divestment and Sanctions movement targeting the Jewish state, which he had long claimed to reject.

“Thank God I still have a lot of support within the Jewish community,” the progressive lawmaker, who is endorsed by such far-left Jewish groups as Jewish Voice for Peace, which supports BDS, said in an interview on Monday with the WNYC radio host Brian Lehrer.

But his text to the Jewish leader, just a couple of months before his first campaign for reelection last cycle, suggests that Bowman, 48, has long been at least privately aware that his relationship with a key constituency over his record on Israel has been on shaky ground — and could be a political liability. 

Bowman’s campaign did not respond to a request for comment from JI on Monday.

Bowman and his allies have sought to cast his primary as a battle against right-wing interests funding attacks from the pro-Israel lobbying group AIPAC, whose super PAC has invested more than $11 million in the race.

Some progressive Jews who back Bowman say they appreciate the congressman’s outspoken criticism of Israeli Prime Minister Benjamin Netanyahu and his support for a cease-fire, while arguing that AIPAC’s involvement in the race does not serve the interests of voters.

But the congressman’s focus on outside spending has obscured an on-the-ground reality reflected in what Jewish voters describe as their widespread disenchantment with his lack of meaningful outreach both before and after Hamas’ attacks.

Notwithstanding his hard-line positions on Israel, Jewish leaders contend that Bowman’s tenure has also been defined by a lack of interest in engaging with the organized Jewish community on a personal level — by ignoring invitations to join Shabbat meals, for instance, or skipping events sponsored by the Westchester Jewish Council, among other things, according to multiple people who spoke with JI.

William Schrag, who recently stepped down from his position as the longtime president of the Westchester Jewish Council, said that the last event Bowman attended was the group’s annual gala in February 2023. The congressman “arrived two hours late — in the middle of our program,” Schrag noted.

When Bowman was first elected to the House, defeating a pro-Israel incumbent, Schrag said that he and the Westchester Jewish Council’s CEO “reached out to him and his staffers immediately” and “had several conversations via Zoom” that each ended with the congressman “or one of his staffers saying we needed to consult with one another, particularly on areas where we might disagree.”

“However, we weren’t consulted before Congressman Bowman flipped on the Abraham Accords and I don’t recall having been consulted since that time,” Schrag told JI last week. “That said,” Bowman “was always invited to events sponsored by the council,” Schrag added. “He chose not to attend and frankly, by that point, I didn’t care whether he attended or not because it was obvious he was on a path antithetical to the mission statement of the Westchester Jewish Council.”

Many Jewish leaders share a similar feeling. 

Early in his incumbency, Bowman, who drew backlash from the left for visiting Israel and voting in favor of Iron Dome funding during his first term, had also briefly maintained an ongoing dialogue with a group of local rabbis with whom he discussed Middle East policy and other issues of concern to the Jewish community. 

Those conversations have all ended as his stances on Israel have shifted to the far left over the last couple of years. The rabbis “have since stopped responding to him,” according to a Jewish activist familiar with the matter.

Justin Brasch, a White Plains councilman and a Jewish Democrat who is supporting Latimer, said that until last summer, he had “worked hard to try to build a bridge with” Bowman, whom he had met for breakfast late in the congressman’s first term to discuss Jewish community issues, exchanging multiple follow-up texts on Middle East policy.

But Brasch, one of several Jewish leaders who urged Latimer to mount his challenge, has since given up on Bowman, citing the congressman’s boycott of Israeli President Isaac Herzog’s address to a joint session of Congress last July as a deal-breaker. 

“That is not someone who wants to build bridges with Jews and the Jewish community,” Brasch said of Bowman in an interview with JI on Friday. “He doesn’t reach out. He doesn’t reach back. He’s not interested at all in the Jewish community.”

To some Jewish leaders in the district, Bowman’s long-deteriorating relationship with Jewish voters has now reached its nadir thanks to his decision to support BDS, which is widely viewed as antisemitic within the Jewish and pro-Israel communities.

His about-face on the movement, in a private endorsement interview with the Democratic Socialists of America last month, has convinced some Jewish leaders that Bowman simply cannot be trusted to represent a district that is home to one of the largest Jewish constituencies in the country.

“He doesn’t tell the truth,” Amy Paulin, a Democratic state assemblywoman in Westchester who is among several local elected officials backing Latimer’s campaign, said in a recent interview with JI. 

Paulin, who called the congressman’s endorsement of BDS “clearly antisemitic,” recalled that the first time she met Bowman in person, during a meeting with the Scarsdale Democratic Town Committee in late 2019, “we specifically asked him if he supported the BDS movement — and he said ‘absolutely not.’” 

Now, she said, “it’s clear that he does — and that he’s lied to us the entire time.”

“I don’t believe anything he says anymore,” Paulin said of Bowman. “That goes beyond the Jewish community, but certainly we in the Jewish community have no confidence in his support or empathy or camaraderie. You just can’t trust him.”

For his part, the Jewish leader whom Bowman asked for a photo last election cycle told JI he no longer speaks with the congressman — and hasn’t for some time — because of disagreements over Israel that he described as ultimately irreconcilable. 

“He’s completely embraced the other side,” the Jewish leader said of his representative.