Jack Schlossberg reacts to Madonna's wild sex claim about late uncle John F. Kennedy Jr
Thomas Bamford
Featured Image Credit: Michael Buckner/Penske Media via Getty Images
JFK's grandson is running for Congress, but that didn't stop him from giving a very candid response to one of Madonna's most outrageous claims.
There are not many situations in which a congressional candidate is asked to publicly weigh in on their late uncle's bedroom antics.
But Jack Schlossberg found himself in exactly that situation this week, and handled it pretty well.
Appearing on Radio Andy's Andy Cohen Live, the 33-year-old Democratic candidate for New York's 12th Congressional District was asked to respond to Madonna's now infamous claim that John F. Kennedy Jr. was the best sexual partner she ever had.
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After a moment of laugher, Schlossberg composed himself and delivered what might be the most diplomatically mischievous answer of the 2026 campaign season so far.
"Well, I'm running for office - so I've got to figure out what to say," he said, before adding: "All I can say is that, um, I bet she was right."
Madonna made the claim while promoting her new album Confessions II, teaming up with Grindr and a group of celebrities for a Q&A session ahead of the release. When asked who her best sexual partner had been, the 67-year-old set one ground rule before answering.
"I'm only going to name dead people," she said, before name dropping JFK Jr.
Designer Raul Lopez was quick to co-sign the assessment. "Everyone says his d*** was crazy and he was a good f***," he told Madonna.
"You're the third person I've heard say that." Madonna's response was a simple "mmm hmm."
The pair dated briefly in the late 1980s, when Kennedy Jr. was working as an assistant district attorney in Manhattan and Madonna was, by most accounts, the most famous woman on the planet. According to biographer Christopher Anderson, author of The Day John Died, Kennedy Jr. was "dazzled by the notion of dating Madonna" and was "not above being star struck."
A dancer friend of Madonna's reportedly said you could "see it in his eyes that first time they met."
The relationship did not last. Friends of Kennedy Jr. later described it as "totally a fling" driven by physical attraction rather than anything deeper.
The situation was further complicated by the fact that Madonna was technically still married to Sean Penn at the time, which reportedly did not go down well with Kennedy Jr.'s mother, former First Lady Jacqueline Kennedy Onassis. Kennedy Jr. went on to marry Carolyn Bessette in 1996 before his death in a plane crash in 1999 at the age of 38.
For those unfamiliar, Schlossberg, full name John Bouvier Kennedy Schlossberg, is the only grandson of President John F. Kennedy and Jackie Kennedy Onassis, and the son of former US Ambassador Caroline Kennedy.
Born in 1993, he first came to public attention as a viral social media personality before launching a bid for Congress in the 2026 midterms.
He is running for New York's 12th Congressional District under the slogan "Believe in something again", with a platform centred on fighting corruption, a tax deduction for renters, and expanding the federal Nurse Corps.
His run makes him the first direct descendant of JFK to seek elected office, and he faces a competitive primary field including New York state assemblymen Micah Lasher and Alex Bores.
Whether his endorsement of his uncle's late-night reputation will help or hinder that campaign remains to be seen. It did, however, make for very good radio.