Trump Uses Loose Ties To JFK Jr. And Carolyn Bessette To Inflate His Own Ego (Surprise, Surprise)

President Donald Trump has had a complicated relationship with the Kennedy family over the years. While you would think RFK Jr. would have rethought his Trump endorsement after what the president had said about his family, it ultimately landed him a gig as the U.S. Secretary of Health and Human Services in February 2025. However, in an interview with Fox News on March 26, Trump was boasting about his new favorite Kennedy.

"American Horror Story" director Ryan Murphy's latest series, "Love Story," follows the heartbreaking romance of first son JFK Jr. and his wife, Calvin Klein fashion executive Carolyn Bessette. The family has always had a place in the spotlight, even decades after President John F. Kennedy's untimely death in November 1963. The success of the series has had the couple on everyone's lips and minds – including the president's.

Trump's appearance on Fox's "The Five" started with discussions of the war on Iran, his MAGA supporters, and rehashing his petty attack on California Governor Gavin Newsom's "cognitive deficiency" up until Dana Perino mentioned the popular new series, asking the president if he had known JFK Jr. personally. "I actually knew him and liked him, and he liked me, believe it or not," Trump claimed, bragging about how the first son had put Trump on the cover of his magazine, George (although People would clarify that Trump's cover came out in 2000, a year after JFK Jr. and Bessette died in a tragic plane crash).

The world of New York socialites is relatively small, and President Donald Trump claims to have gotten very close to first son JFK Jr. and his wife Carolyn Bessette beyond run-ins in Manhattan. He told Fox's "The Five" that the couple would frequent his Mar-A-Lago resort in Palm Beach, Florida, sharing how "They would bicker together, in other words have little fights, and then they would make up and start kissing wildly." While their apparent arguments would lead Trump to believe "It was one of those relationships, and you never know how those relationships are going to turn out," their sudden passing signaled a lot more than the end of a highly publicized romance.

Trump told Dana Perino, "I think [JFK Jr.] would have gone on, perhaps, to be the president," claiming that Kennedy had personally told him about his plans to sell George magazine in order to pivot into politics – although he would have apparently preferred to become a Broadway actor. Trump was adamant that Kennedy would have won a bid for New York senator, and also interjected multiple comments about how handsome the businessman was.

Trump notoriously had Broadway ambitions back in his early 20s, and his takeover as chairman of the Kennedy Center in February 2025 is evidence that he's still holding onto those dreams. The president clearly has a lot of admiration for the late John F. Kennedy Jr., but we can't help but notice how a lot of the first son's supposed plans for his future mirror Trump's own ambitions.