How This Democrat Legacy Became An ‘Outsider’

Jack Schlossberg, the only grandson of former President John F. Kennedy, is entering the race for Congress in New York City, positioning himself as an outsider despite belonging to one of the most recognizable political families in American history.

Schlossberg, the son of Caroline Kennedy and the late Edwin Schlossberg, is running in New York’s 12th Congressional District, where longtime Democratic Rep. Jerry Nadler announced his retirement after more than three decades in office. The open seat has triggered a crowded Democratic primary scheduled for June 23, with roughly a dozen candidates competing for the nomination.

Despite his family’s political legacy, the 33-year-old candidate says he is battling a powerful local political machine that he believes wants to control who ultimately replaces Nadler in Congress.

“It’s probably hard for people to believe me saying that I’m an anti-establishment outsider given my family ties, but in this race, I really am,” Schlossberg said in an interview with Fox News Digital.

He argued that party insiders, donor networks, and political clubs in the district are attempting to shape the race before voters have their say.

“I am going up against a political machine here in NY-12 that doesn’t want change,” Schlossberg said. “They want to control the people who they send to Congress, and that means trading favors and endorsements before the seat has even opened up.”

New York’s 12th District, which includes parts of Manhattan and Brooklyn, is one of the most reliably Democratic districts in the country. In the 2024 presidential election, approximately 81 percent of voters in the district supported then–Vice President Kamala Harris. Because of that political landscape, the winner of the Democratic primary is widely expected to prevail in the general election.

Schlossberg faces significant competition from other well-connected Democratic candidates. Venture capitalist Alex Bores and New York State Assemblyman Micah Lasher, a longtime political ally of Nadler, are both considered strong contenders and currently lead Schlossberg in fundraising and cash on hand.

Several influential Democratic organizations have also lined up behind rival candidates. The Four Freedoms Democratic Club and the national political group The NewDEAL have endorsed Bores, while the Eleanor Roosevelt Independent Democrats have backed Lasher.

Schlossberg, however, says his campaign is focused on grassroots organizing rather than institutional support. He highlighted his pledge not to accept donations from corporate political action committees, super PACs, or major artificial intelligence companies.

“I’m the only candidate who’s gone out and said I won’t take money from corporate PACs, from super PACs, or from big AI companies,” he said. According to Schlossberg, the average donation to his campaign is roughly $40, which he says reflects a people-driven effort.

He pointed to one recent event as evidence of enthusiasm among supporters. After promoting a gathering on social media during a snowstorm, Schlossberg said hundreds of volunteers showed up the following day ready to help with the campaign.

Still, critics question his outsider narrative. An operative working for one of his rival campaigns told Fox News Digital that lacking political experience does not automatically make someone an outsider.

“Not having accomplishments or a track record doesn’t make you an outsider,” the operative said. “It makes you unqualified.”

Schlossberg has also drawn attention for his progressive political positions and outspoken criticism of the Trump administration. He has faced criticism from conservatives over past social media posts and policy proposals. At the same time, he has embraced anti-establishment messaging similar to that used by other progressive candidates in New York politics.

Among the policy proposals he highlights are a “standard renters deduction” that would allow renters in the district to deduct a portion of their rent from federal income taxes, trade reforms aimed at lowering consumer prices by revisiting certain tariffs, and increased federal funding for security upgrades at houses of worship.

He has also proposed a measure he calls the “Ricochet Rule,” intended to limit the flow of illegal firearms into New York that are later used in criminal activity.

Schlossberg says that despite resistance from political insiders, he believes voters are open to his message. He joked that while some supporters may hesitate to publicly back him due to local political pressures, the outcome will ultimately be decided privately at the ballot box.

“Now I understand why the United States has secret ballots,” he said.

With the Democratic primary approaching in June, the race to replace Nadler is shaping up as one of the most closely watched congressional contests in New York City.

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