Jamaal Bowman may be the most endangered Squad member. He doesn't seem alarmed.

• Rep. Jamaal Bowman is in the fight of his political life ahead of the June 25 primary.

• He's been outraised by George Latimer, a local politician backed by pro-Israel groups.

• A Bowman loss would be the biggest setback for the left since the end of Bernie Sanders's 2020 bid.

It was a bright, chilly spring day in the coastal village of Port Chester, New York, where Rep. Jamaal Bowman and the man who could run him out of Congress — Westchester County Executive George Latimer — found themselves in the same small public park.

Local workers and labor activists were there to commemorate Worker's Memorial Day, an international day of remembrance for those who have died or been injured on the job. As Bowman delivered a booming 4-minute speech over the din of passing cars and the screeching of nearby construction, Latimer stood silently beside State Sen. Shelley Mayer, one of a litany of local politicians and Democratic Party officials who have backed the county executive over the congressman.

As a procession of speakers took turns assailing local developers and contractors for sidelining organized labor, exploiting undocumented workers, and failing to safeguard against hazardous workplace conditions, Bowman placed his arm around mine and another reporter's shoulders and brought us in.

"My opponent," Bowman whispered slowly, as Latimer stood just a few yards away, "received an award from developers."

Later that afternoon, sitting in the back hatch of his car outside a high school in Mount Vernon, the congressman suggested that Latimer is running a racist campaign against him. The county executive, whose primary slogan is "results over rhetoric," has at times sought to highlight Bowman's boisterous personal style as a distraction from the issues that the district is facing. During his current term, the congressman has had public, attention-getting spats at the Capitol with the likes of Reps. Marjorie Taylor Greene, Thomas Massie, and George Santos.

"That's racist dog-whistle shit," Bowman told me. "Historically, Black men haven't been allowed to be loud, Black women either, right? Certain groups aren't allowed to be loud, we're not allowed to be outspoken, we're supposed to be quiet and thankful that the white man has even given us an opportunity to not be slaves."

"He's coming up with a rationale on identity because he doesn't have a substantive enough argument to justify [his reelection]," Latimer told me over Zoom the following week. "He's fishing for an angle here that doesn't exist."

Bowman's primary has clear national implications: He may be the single most endangered member of the progressive "Squad," along with Rep. Cori Bush of Missouri, and either of their defeats would mark the biggest electoral setback for the left since the end of Sen. Bernie Sanders's 2020 presidential campaign. Owing to Bowman's views on Israel, deep-pocketed groups — including a super PAC affiliated with the American Israel Public Affairs Committee (AIPAC) — are expected to spend tens of millions of dollars to unseat the congressman ahead of the June 25 primary. If polling is to be believed, Bowman is already in deep trouble: an internal campaign poll showed the congressman ahead by just 1 point, while another poll commissioned by Democratic Majority for Israel showed him trailing Latimer by 17 points.

"He was recruited by AIPAC to run against us because we called for a permanent cease-fire," Bowman said of Latimer. "He's literally running on the war crimes of Benjamin Netanyahu."

But it's not just Bowman's pro-ceasefire position that has imperiled him. Since September — when he infamously pulled a fire alarm in a House office building — Bowman has faced a rolling series of controversies, particularly his dismissal of reports of sexual violence on October 7 as "propaganda" and the surfacing of his past history of dabbling in 9/11 conspiracy theories. He has since backtracked and apologized on both counts, but also insists that they aren't a big deal.

"I'm like, are y'all serious? Y'all don't have much of anything present-day, so you bring up a blog I wrote 10 years ago," Bowman said of the 9/11 conspiracy theories. "That stuff never comes up. What comes up most of all, is 'thank you for your support of Palestinians, thank you for the work you do, we hate that [Latimer's] running.'"

Bowman's belief that Israel is committing genocide in Gaza — while increasingly accepted by most of the Democratic base — has not helped his reelection prospects in a district home to an estimated 110,000 Jewish people, many of whom remain supportive of Israel and repulsed by the congressman's views. In January, Bowman lost the support of the liberal pro-Israel group J Street over his rhetoric on Israel.

But if Bowman's worried, he's not showing it. When I visited the district in late April, he told me that the campaign has felt "similar to the energy that we felt in 2020," when he first unseated longtime Democratic Rep. Eliot Engel in the midst of the COVID-19 pandemic.

'The fire alarm incident is troubling'

George Latimer has a deep history as an elected official in Westchester, beginning with a stint on the city council of Rye — one of the New York state's wealthiest communities — in 1987. He then served a 13-year stint in the county legislature, eight years in the state assembly, and another five in the state senate until 2017, when he defeated Republican Rob Astorino to become county executive, a position akin to that of a governor in a county of roughly one million people.

Latimer insists that his decision to challenge Bowman was reluctant, that he saw his congressman as trying to be the "spokesperson for a national movement" rather than focusing on the needs of the district. "The elected congressman is not going to be the secretary of state," Latimer told me. In fact, the county executive largely sought to downplay the national impact he might have as a member of Congress, saying that there's "not going to be a George Latimer climate change bill" and that he "won't be there long enough to become a committee chairman, let's be honest."

Like Bowman, Latimer has a blunt and direct speaking style that sometimes leades to gaffes, such as his invocation of the racist lynching of Emmett Till when commenting on the sexual misconduct allegations against then-Gov. Andrew Cuomo in 2021. When asked about Bowman's charge of racism, Latimer pointed to his appointment of Ken Jenkins, a Black man, as his deputy county executive. "No racist person does that," he said. Latimer has also taken heat during this primary for accusing Bowman of "taking money from Hamas," an apparent reference to the fact that some organizers of a Bowman fundraising event characterized the October 7 Hamas attack as an act of resistance.

In contrast to Bowman's characterization of Latimer as merely an AIPAC recruit, the county executive said that he'd been approached as far back as the spring of 2023 about running, both by members of the Jewish community and "people in the business community who felt that [Bowman] really wasn't an advocate" for them. Latimer indicated that he would be far more of a bipartisan legislator than Bowman, throwing out the names of Republicans like Reps. Brian Fitzpatrick of Pennsylvania or Tom Kean of New Jersey as potential partners on flooding issues. "I would try, in a mature way, to have good relations with as many people as I could," he said.

"I have to tell you that the fire alarm incident is troubling," Latimer said, unprompted, during our conversation. "He pulled the alarm purposefully. It's clear, it's clear."

The congressman has long maintained that the September 30 incident, which came as House Democrats were seeking more time to review a stop-gap government funding bill before voting on it, was an accident. He has since paid a $1,000 fine, pleaded guilty to one misdemeanor count of pulling a fire alarm, and was censured by the House — including three fellow Democrats — in December. Latimer argued that the security camera footage of the incident showed that Bowman was "willing to just flat-out misrepresent what he did."

"It doesn't really come up at all. I mean, the fire alarm thing, people almost immediately knew it was BS in terms of how it was being blown up," Bowman told me. "Honestly, anyone who's going to vote against me because of that, versus my record, it's like, okay, you weren't really a supporter anyway."

Bowman's record is also a topic of contention: the congressman claims to have brought over $1 billion in federal funding back to the district. While over $40 million came in the form of so-called "earmark" funding in annual government spending bills that were directly secured by Bowman, the vast majority of that sum came from federal funding streams and grants where his involvement was far less direct, as local outlets have noted. "He hasn't delivered anything like a billion dollars to the district," said Latimer. "That's a bogus claim."

Bowman and Latimer have known each other for nearly four years, first meeting for coffee after the congressman's 2020 primary victory. But despite serving the same area, both indicated that they have little relationship with one another. "I'm not trying to be snide, I just don't see him much out in most of the Westchester community," said Latimer. "It hasn't been much of a relationship, not necessarily bad, but just hasn't existed much over the last two years, maybe more." Bowman, for his part, said Latimer's team was "always lukewarm at best, and never really reciprocated the genuine love and respect that I had for him, and all my colleagues when I engage them."

'AIPAC is not a racist organization'

It goes without saying that Israel is the defining issue of the race. Bowman's call for a cease-fire in the days after October 7 and his continued criticism of Israel — including voting against a recent tranche of military aid — enraged plenty of his constituents and helped catalyze Latimer's campaign. The congressman has frequently pointed to a March poll commissioned by the Working Families Party, a progressive group that supports Bowman, showing that 69% of the district's residents support a cease-fire.

When I asked Latimer about his own views on Israel's war in Gaza, he declined to outline the circumstances under which he may support conditioning military aid, saying that he simply trusts President Joe Biden and wants him to have the "maximum amount of flexibility" to deal with the war without congressional restrictions. "I get very frustrated when I hear people talking about what Israel is doing, what Israel is doing, what Israel is doing, and we don't talk about what Hamas has done," Latimer said. "Do I think Israel could do better? Everybody could do better."

A central character — and boogeyman — in this primary is AIPAC, the decades-old bipartisan advocacy group whose staunchly pro-Israel positions are increasingly to the right of a Democratic Party that's grown more sympathetic toward Palestinians. Progressives frequently note that AIPAC supports Republicans who voted against certifying the 2020 election results (though plenty of other bipartisan groups and PACs do the same thing). Furthermore, AIPAC's "United Democracy Project" super PAC is sustained in large part by multimillion-dollar contributions from Republican megadonors, even as the PAC spends mostly in Democratic primaries — most often against non-white progressive candidates.

"It's an attempt by the megadonors who prop up Donald Trump and the MAGA movement to attack and defeat a handful of Black and brown progressive incumbents," Justice Democrats spokesman Usamah Adrabi told me of AIPAC, deriding Latimer as an "empty suit that is just a vessel for Republican billionaires to attack and malign Jamaal Bowman."

A little more than a third of Latimer's contributions have been routed through AIPAC, and a Working Families Party analysis provided to Business Insider shows that hundreds of thousands of dollars have flowed to the county executive's congressional campaign from donors who have given mostly to Republicans, including Donald Trump. Latimer told me that he's "always gotten support from Republican people" because of his focus on "getting things done" as an elected official. "Those donors have donated to me primarily because of my position on Israel, not because I'm pro-choice or pro-LGBTQ," he said.

"AIPAC is not a racist organization," Latimer added. "They say that, 'Oh, it goes after Black individuals.' Well, it goes after Squad members, not because they're Black, but because they've been anti-Israel in their various positions."

Latimer has reported raising $3.6 million since he launched his campaign, while Bowman has raised $2.7 million since January 2023. The county executive also boasts far more local financial support: Roughly 70% of Latimer's itemized contributions come from donors in New York state, and roughly half of them are from the district. Meanwhile, just 28.5% of Bowman's itemized contributions come from New York and just 10% come from the district, while a plurality — nearly 31% — come from California.

"He's raising [money] from interests outside the district that are clearly not local," said Latimer. "I'm getting it from people who are local, who don't like him, and want me as an alternative."

'They're not against me just because of my policies on Israel'

Part of what's made the race so contentious is the geography of the district, which spans predominantly-Black communities in the Bronx and Mount Vernon, to more Latino and mixed cities like Yonkers and New Rochelle, to predominantly white and heavily Jewish townships like Scarsdale, Rye, and Harrison. Both men have accused the other of not representing the entirety of the district, and both of them may have a point.

"The district represents the country in a couple of ways," said Bowman, who has long lived in the Bronx. "It's diverse, but it's also segregated as hell." The congressman speaks somewhat dismissively of the wealthier parts of the district that lie deeper into Westchester. "They're not against me just because of my policies on Israel," said Bowman. "I'm also pro-worker over corporations, I have bills that's about taxing the wealthy and making sure corporations pay their fair share."

"He didn't travel into Scarsdale and Harrison and get to know the people there," Latimer said of Bowman. "He focused on a few communities that he felt he could connect to, and he has his relationships there, and he ignored the rest of the district."

Latimer has his own challenges, largely stemming from the fact that he's a white man seeking to unseat a Black incumbent in a majority-minority district. Though he grew up in Mount Vernon, Latimer has long lived in Rye, and the core of his support lies in the district's more affluent communities. "I freely admit that in the Bronx, I'm going from zero to somewhere, because I haven't represented the Bronx," said Latimer. "You know, it's a learning curve."

But the county executive insists that it's "baloney" to say that he only represents the wealthy parts of the district, ticking off the endorsements he's garnered from Democratic committees in majority-minority communities, his support from a local bus drivers' union — "these are people who live in urban settings, and the way that I've worked with them and dealt with them is absolutely positive" — his work on a Black maternal health initiative, and the work that his county government did to repair Memorial Field, a stadium that's "primarily used by young people and African American young people in Mount Vernon."

It was at Mount Vernon High School where Bowman — a longtime educator who founded a middle school in the Bronx in 2009 — seemed especially in his element. Striding through the halls on his way to the auditorium, he remarked that the school "used to be off the chain," but that a new principal had "really turned it around" in recent years. As he addressed a room full of predominantly-Black students at a "Shark Tank"-esque career education competition, he held up his iPhone while urging them not just to get a job, but to create jobs. "Do you want to work for Apple, or do you want to build and create the next Apple, or the next company that's even better?" asked Bowman. "Do you want to have an iPhone and use it? Or do you want to create a new cellphone no one ever thought of or heard of before?"

Outside the high school, Bowman remarked that "Black women are the biggest barometer" for him when it comes to evaluating some of the missteps he's made, given that "they see me as their son or grandson."

"The biggest thing I get from them is like, stay out of trouble," said Bowman. "Because they remember the civil-rights movement, they know history, they know what happens to us when we get in these positions, and we screw it up."

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