Trump's a secret fan of a popular young Democrat: biographer

U.S. President Donald Trump dances after delivering remarks to members of the Republican Party, at Trump National Doral Miami in Miami, Florida, U.S., March 9, 2026. REUTERS/Kevin Lamarque

President Donald Trump is reportedly a big fan of Jack Schlossberg, the grandson of the late President John F. Kennedy — even though Schlossberg is a staunchly anti-Trump Democrat.

“He’s kinda enamored with this kid,” journalist Michael Wolff told The Daily Beast regarding his inside sources’ information about the Republican president’s attitudes toward the Democratic dynastic scion. “I’m sure the poor guy does not want a Trump endorsement, but it really sounds like Trump is tickled by this.”

Wolff added that, even as Trump is souring on Schlossberg’s cousin Secretary of Health and Human Services Robert F. Kennedy Jr., he believes the younger Kennedy has political potential.

“Trump has been saying, that guy seems like maybe he’s the real thing, he’s the grandson,” Wolff said. By contrast, his perception of the cousin is that "RFK is a problem. Let’s push him this way. And then to praise the cousin—who is condemning him.”

Schlossberg, who is currently running for Congress in New York, is outspokenly critical of Trump. For example, he denounced Trump last month for adding his own name to the Kennedy Center for the Performing Arts.

“Trump can take the Kennedy Center for himself,” Schlossberg said at the time. “He can change the name, shut the doors, and demolish the building. He can try to kill JFK. But JFK is kept alive by us now rising up to remove Donald Trump, bring him to justice, and restore the freedoms generations fought for.”

Schlossberg has also accused Trump of trying to politicize the infamous 1963 assassination of Schlossberg’s grandfather by fueling conspiracy theories about the murder.

“JFK conspiracy theories,” wrote on social media at the time. “The truth is alot sadder than the myth — a tragedy that didn’t need to happen. Not part of an inevitable grand scheme. Declassification is using JFK as a political prop, when he’s not here to punch back.”

Schlossberg’s older sister Tatiana is also a vociferous critic of Trump. On the 62nd anniversary of the Kennedy assassination in November, Tatiana — who passed away from a rare blood and bone marrow cancer in December at the age of 35 — said that her family was afraid as they saw Robert F. Kennedy Jr. support Trump and get confirmed as Secretary of Health and Human Services.

“Throughout my treatment, [RFK Jr.] had been on the national stage: previously a Democrat, he was running for president as an Independent, but mostly as an embarrassment to me and the rest of my immediate family,” Schlossberg wrote at the time.

“I watched from my hospital bed as Bobby, in the face of logic and common sense, was confirmed for the position, despite never having worked in medicine, public health, or the government.”

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