Celebrity4 min(s) read
Published 09:30 02 Jun 2026 GMT
A biographer has made an eyebrow-raising claim about John F. Kennedy Jr's manhood after Madonna's recent bedroom confession.
The Queen of Pop stunned fans last week while promoting her upcoming album, Confessions II, when she named the son of former President John F. Kennedy as the best lover she'd ever had.
The confession came during a video created in partnership with Grindr, where Madonna joined playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and Interview magazine's Marcello Gutierrez for an unconventional Q&A.
When Lopez asked: "Who was your best d*** down?," the Vogue hitmaker replied: "I’m only going to name dead people," before covering her mouth and whispering: "John Kennedy Jr."
The room immediately erupted in disbelief. "Shut the **** upppppppp!" the group shouted back.
Lopez then added: "Everyone says his d*** was crazy and he was a good f***."
"Mmm hmm," Madonna confirmed. "You’re the third person I’ve heard say that," Lopez continued.
The pair were linked in the late 1980s while her marriage to actor Sean Penn was nearing its end.
Although details of their relationship remain scarce, people close to the late attorney have offered occasional glimpses into what allegedly happened between them.
According to the 2024 book JFK Jr.: An Intimate Oral Biography by Rosemarie Terenzio and Liz McNeil, the relationship was never particularly serious.
"Madonna was totally a fling," one of Kennedy's close pals said. "Nothing more. Barely a fling at that."
The book claims Kennedy was dating actress Christina Haag when he met Madonna and alleges that she pursued him because "she was at the top of her game".
Authors also claimed: "He loved her body. It was all about physical attraction; it wasn’t going to be anything beyond that."
The renewed attention on Kennedy’s love life comes as interest grows in Ryan Murphy’s series Love Story: John F. Kennedy Jr. & Carolyn Bessette, which premiered earlier this year.
The nine-episode drama, available on Hulu and Disney+, follows the romance, relationship, and marriage of Kennedy and Carolyn Bessette-Kennedy before their deaths.
The show is based on Elizabeth Beller’s book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy.
While the series attracted plenty of attention, it also faced criticism from people close to the Kennedy family, who questioned its accuracy.
One of the strongest critics was Kennedy’s nephew, Jack Schlossberg.
The 33-year-old spoke on CBS's Sunday Morning after the show's release in February, and said: "Well, if you want to know someone who’s never met anyone in my family, knows nothing about us, talk to Ryan Murphy."
"I would just want people who do watch the show to watch it with one letter in mind, and that’s a capital F for fiction," he continued. "The guy knows nothing about what he's talking about, and he's making a ton of money on a grotesque display of someone else's life."
Author Maureen Callahan, who wrote the 2024 book, Ask Not: The Kennedys and the Women They Destroyed, also challenged aspects of Kennedy's portrayal.
One scene in the series shows JFK Jr. discussing intense media scrutiny with his cousin, Anthony Radziwill, inside a locker room. After Radziwill jokes about Kennedy's willingness to expose himself at the gym, Kennedy responds: "Apparently, that’s all I’m good for."
Callahan believes that line was completely out of character. Speaking on her podcast The Nerve With Maureen Callahan, she argued: "John Jr. was such an exhibitionist...So, you’re going to tell me, 'the big bad media'? He loved the media attention.
"He loved nothing more than ripping off his shirt and running around in Central Park, okay? And making sure all the paparazzi got great views, okay? Great sight lines," she said before making an even more shocking claim about his behaviour at the gym.
"He would walk around the gym naked all the time. Like picking at his pubic hair and inspecting his genitalia, like teasing other men."
Kennedy Jr.'s life was cut short in July 1999 when the small aircraft he was piloting crashed into the Atlantic Ocean near Martha's Vineyard, Massachusetts.
His wife, Carolyn Bessette-Kennedy, and her sister, Lauren Bessette, were also on board.
All three died in the crash.
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