Jack Schlossberg, the grandson of former President John F. Kennedy, is making a play for Congress in New York by casting himself as an outsider. But the weight of his family's political dynasty—one of the most storied in American history—makes that a tough sell.
Schlossberg, who does not use the Kennedy surname, is leaning into the same anti-establishment energy that has propelled outsider candidates across the country. From Texas to Maine, voters have shown a growing appetite for fresh faces who challenge the political status quo.
In Texas, state Rep. James Talarco, a relatively unknown figure, stunned the establishment by defeating Rep. Jasmine Crockett in the Senate Democratic primary. In Maine, oyster farmer Graham Platner generated enough buzz to force Gov. Janet Mills to suspend her campaign. And closer to home, New York City Mayor Zohran Mamdani won office by tapping into voter frustration over affordable housing and the political class.
Schlossberg has been quick to align himself with that wave. On Instagram, he reminded his 880,000 followers that he endorsed Mamdani twice. His campaign now argues that his policy proposals—including a first-of-its-kind plan to support nurses and expand elder care, and a New York Housing Fairness Plan that would let renters deduct a portion of annual rent—set him apart from career politicians.
“People want to believe in something again,” a Schlossberg spokesperson told The Hill. “Jack’s campaign is the only one offering up new ideas, new energy, and a new way of doing things—because the others in this race are happy with the old way, relying on insiders and billionaires to win.”
But Democratic strategists are skeptical. Brad Bannon, based in Massachusetts, put it bluntly: “A Kennedy by definition is the ultimate insider. Jack Schlossberg has as much chance of winning as an outsider as I do starting at shortstop for the Red Sox this season.”
Anthony Coley, a former spokesperson for the late Sen. Ted Kennedy, added: “It’s generally hard for anyone with a famous last name to be perceived as an outsider.”
The Kennedy family is enjoying a cultural resurgence, thanks in part to a recent TV series about John F. Kennedy Jr. and Carolyn Bessette Kennedy that has captivated younger audiences on TikTok. One strategist noted that Schlossberg likely benefits from that renewed fascination. But another pointed out that he has yet to fully articulate why he’s running, beyond invoking his grandfather’s legacy.
“I have yet to hear what truly makes him different from the other options out there,” the strategist said. “He’s struggling with that a bit. This is not the ideal year for making that argument.”
Schlossberg has acknowledged the challenge. “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,” he told Fox News Digital in March. “I am going up against a political machine that doesn’t want change.”
Meanwhile, the broader political landscape continues to shift. In Texas, a new poll shows voters evenly split on election integrity versus ballot access, highlighting the complex dynamics at play in this cycle. And in South Dakota, Sen. Mike Rounds is expected to cruise past his primary challenger, a reminder that incumbents still hold advantages in some races.
