What a difference four years makes. Around this time in 2020, the activist left was riding high. Joe Biden had clinched the Democratic presidential nomination, but he incorporated left-wing demands into his policy platform. Democratic Reps. Alexandria Ocasio-Cortez (N.Y.), Rashida Tlaib (Mich.), Ayanna Pressley (Mass.) and Ilhan Omar (Minn.) — the group of left-wing insurgents that became known as “the Squad” — were shaking up Congress, and Justice Democrats, the upstart progressive outfit that recruited Ocasio-Cortez, was spoiling for more moderate Democrats to take down.

Jamaal Bowman, a Black middle school principal from a humble background with an authentic love for the Wu-Tang Clan and Nas, seemed like a good fit to oust Rep. Eliot Engel, an aging white man with staunch pro-Israel views who represented New York’s 16th Congressional District, a majority-minority district straddling the New York City border. A progressive ecosystem was already mature enough to provide Bowman with professional fundraising, polling and even a super PAC, pushing him to a groundbreaking victory that year.

But just as Bowman’s victory in 2020 was a sign of rising progressive fortunes, so too does his defeat reflect a receding of the progressive wave. With Donald Trump out of office, grassroots energy and fundraising have grown scarcer. A backlash to the Black Lives Matter movement and other left-wing cultural forces is still a major factor in Democratic primaries. And the ideological terrain on which the left is now fighting has attracted the ire of the well-financed pro-Israel lobby.

Put together, it paints a picture of a progressive movement past its prime, with Bowman’s loss on Tuesday potentially just the latest sign of how much more hostile the environment has become for aspiring left-wing candidates.

Indeed, a number of key factors working in Bowman’s favor in 2020 were largely matters of, well, timing. For one thing, the big donor response to the activist left was only in its infancy. The main pro-Bowman super PAC beat the Democratic Majority for Israel, a pro-Israel group, to the TV airwaves and was not heavily outspent. But DMFI, a pioneer in the fight against the contemporary left, was largely on its own in 2020.

The following year, the American Israel Public Affairs Committee would erect its own super PAC, which proved capable of raising and spending tens of millions of dollars rather than just millions. In 2024, AIPAC, which endorsed Westchester County Executive George Latimer, Bowman’s challenger, would spend nearly $15 million trying to bury Bowman. While Bowman’s candidacy was weighed down by his own baggage, there is no question that AIPAC’s largesse is shaping which candidates run and how they formulate their positions.

Here are four more takeaways:

Changing Priorities

Bowman won his first race less than a month after the police murder of George Floyd, a moment when support for the Black Lives Matter movement was historically high among white liberals. The climate likely helped Bowman, who ran on combating systemic racism and police misconduct.

“You know what Donald Trump is more afraid of than anything else? A Black man with power,” Bowman declared in his victory speech.

Now, amid Israel’s ferocious war in Gaza, the American left has made championing Palestinian rights and a cease-fire the central focus of its movement. The emphasis on Palestine, which is sometimes louder than messaging about climate action, anti-racism and economic equality, is a justifiable response to an Israeli military offensive with massive civilian casualties that many human rights groups and experts believe has violated the laws of war, or worse.

Politically, the shift in focus has elicited appreciation from Arab Americans and Muslim Americans who feel shut out of the political process. But it has also attracted additional anger from wealthy pro-Israel donors and alienated some otherwise progressive Jewish voters.

Diana Lovett, a former Bowman supporter and donor who backed Latimer, recalled how the “moment” and Bowman’s “message” about racial justice drew her to him in 2020. “I do think that representation matters,” said Lovett, an affordable housing and refugee resettlement advocate who supported Sen. Elizabeth Warren’s (D-Mass.) presidential bid in 2020.

But Lovett, who is Jewish, faulted Bowman for not honoring Jewish Americans’ sense of vulnerability after Hamas’ terror attack on Israel on Oct. 7. She took issue with his votes against a nonbinding resolution condemning Hamas and a resolution condemning support for Hamas and other designated terrorist groups on college campuses.

“I believe in the need for protection of and representation of minorities in all areas,” she said.

Bowman Was Unprepared

A critical part of Bowman’s success in 2020 was out-campaigning Engel and, in the process, catching him off guard.

At the height of the COVID-19 pandemic, Bowman was hard at work, knocking on doors in his Wu-Tang mask and helping distribute food and other relief supplies. Engel, by contrast, was trying to ride out the pandemic in his home in Potomac, Maryland.

To the outside eye, the events that followed look like a stroke of luck, but they were the result of well-executed campaign staffing and consulting. Bowman’s campaign exposed Engel’s absence by tipping off a prominent mainstream reporter based in Washington, who drove to Engel’s Maryland home and knocked on the door. That revelation prompted him to return to the district, where he was so eager to remind his constituents he was home that he was caught on a hot mic demanding airtime at a press conference with the now infamous line, “If I didn’t have a primary, I wouldn’t care.”

The nonpartisan, court-ordered redistricting ahead of the 2022 cycle may have also hurt Bowman by swapping out chunks of the Bronx in favor of more affluent and less diverse towns in Westchester. (Bowman did pick up some liberal river towns but lost Riverdale, a northwestern Bronx neighborhood with a large Jewish community that likely would have mobilized heavily against him this year.)

Bowman would end up winning just 54% of the vote in the August 2022 primary, demonstrating the tenuousness of his standing in the district.

But perhaps lulled into complacency, he did not gear up for a bruising primary fight in 2024. He had just over $180,000 in cash on hand going into the final quarter of 2023, suggesting a lack of urgency in his fundraising efforts at exactly the moment when his enemies were assessing his strength and laying the groundwork for Latimer’s candidacy. Thanks to AIPAC and his local network of donors, Latimer raised $1.4 million within a month of announcing his bid in December.

“If you have a million in the bank, that’s not nothing for when they’re trying to recruit a challenger,” said a former Bowman campaign aide who requested anonymity to speak freely. “I don’t think it resonated with him in 2022 that 40-plus percent of the district voted against him, and that’s not great.”

All Politics Is Local

In the 2020 election cycle, Bowman notably blasted Engel, who was then chair of the House Foreign Affairs Committee, for focusing unduly on foreign policy. It came, Bowman argued, at the expense of paying attention to his actual constituents.

“I think our district deserves leadership that truly understands the needs of our communities rather than someone who is taking corporate money and seems so focused on foreign affairs,” Bowman said in a 2019 interview with Jacobin.

Once in office, Bowman had become a star on social media for his confrontations with Republican members of Congress. Back home, though, Bowman had to contend with a local Democratic establishment that still viewed him as an unwanted interloper.

Amid last-minute redistricting chaos in 2022, a number of prominent Democrats privately encouraged then-Rep. Mondaire Jones (D-N.Y.), a less radical Black progressive from a neighboring seat, to challenge Bowman in the primary. Neither the Westchester County Democratic Committee nor the Bronx Democratic County Committee endorsed Bowman’s reelection that year. And Jay Jacobs, chair of the New York State Democratic Party, maxed out to one of Bowman’s primary challengers.

Notwithstanding that level of official resistance, even some of his allies think he has not always dedicated enough time to building local relationships. Partly as a result, a precious few local elected officials stood up for him when he pulled the fire alarm as he was rushing to exit a House office building in late September.

“He never built up enough relationships with some groups to get the benefit of the doubt,” said the former Bowman aide.

Kasheem Maclin, a city marshal in Mount Vernon, New York, felt Bowman was not a regular presence in the city.

“Before this election, I’ve never seen Bowman,” Maclin told HuffPost on Tuesday. “I’ve seen Latimer, I don’t know how many times.”

Then, in the fight for his political life, Bowman made AIPAC and the Israeli invasion of Gaza, which he calls a “genocide,” a central theme of his stump speeches. He went so far as to visit the pro-Palestine protest encampment at Columbia University in Manhattan, far outside his congressional district. And Justice Democrats’ super PAC chose to feature the topic in a pro-Bowman television advertisement.

“In 2020, Bowman beat a 30-year incumbent by setting up a clear contrast — between an incumbent who was too focused on foreign policy and himself, a challenger focused on the needs of the district,” said Alyssa Cass, one of Bowman’s press and communications consultants in 2020. “In 2024, Latimer was able to litigate a very similar case.”

Bowman “let himself get defined by an issue that wasn’t top of mind for his voters, only critics who were never going to vote for him,” Cass added.

Bowman’s campaign was also slow to define Latimer with strategically placed opposition research. A story about Latimer’s slow-walking of a federal housing desegregation decree went to print weeks before Election Day. And another item about his vehicle registration being revoked due to unpaid parking tickets never made it out of the niche local press.

All of those factors gave Latimer — by Bowman’s own admission, the consummate “retail politician” — an opening to use a similar line of attack on Bowman as he, four years ago, had used on Engel.

“Jamaal Bowman got out of step with the district. He stopped working the needs of the district,” Latimer said on CNN on Monday. “He stopped caring about every one of the municipalities and the residents there, because there’s a certain amount of national image that he seems to care more about.”

George Latimer Risks Alienating Some Constituents Too

By the time Election Day rolled around, Latimer was the strong favorite to win the race. A public poll in mid-June had him ahead by 17 percentage points — exactly the margin by which he ended up winning.

But in appearance after appearance, Latimer sounded bitter, as if he felt victimized by Bowman’s identity and ability to appeal to Black and Muslim voters.

In a June 10 debate with Bowman, Latimer tied him to donors in the Muslim community and left-wing circles in the San Francisco Bay Area. “Your constituency is Dearborn, Michigan. Your constituency is San Francisco, California,” he said.

And days before the election, Latimer claimed Bowman had an “ethnic benefit” that would net him Black votes.

Those comments hurt Donny Khan, a Muslim resident of Irvington, New York, who helped Latimer campaign in the Muslim community during his 2017 run for county executive.

“George Latimer came to the Muslim community center, took pictures with women in hijabs, took their votes when he needed them,” said Khan, a co-founder of Westchester Progressives and American Muslims Indivisible. “And then ever since he started running [for Congress], because he knows who’s giving him the money, he’s made the Dearborn comment. He’s made the San Francisco comment. He’s talked about the ethnic advantage. Anybody who watches Fox News knows exactly what all of those things mean.”

But Latimer was defensive on Tuesday night when he was asked whether he would reach out to constituents offended by his comments.

He emphasized that he meant to refer to Bowman’s alliance with Tlaib, Congress’ sole Palestinian American member whose district includes Dearborn and who contributed $500,000 to a pro-Bowman super PAC.

“They shouldn’t be offended by the Dearborn comment,” Latimer said to reporters. “I’ve explained it three or four times.”

Pressed on whether he might still need to do outreach to groups irked by some of his language, Latimer blamed the media for misinforming people about his comments.

“There are bridges to be built, and those bridges to be built come from mutual respect and don’t come from attack ads,” he said. “They don’t come from misrepresenting someone else’s position.”

“I had a number of positions that I had misrepresented in this campaign. I’m not beyond defending — I have thick skin,” he continued. “But let’s understand that some people drew judgments about me negatively because of the misrepresentation that was made in some cases — I’m not accusing anybody here — repeated by members of the press as fact.”