Jack Schlossberg may be focused on his congressional campaign, but that did not spare him from being asked about one of Madonna’s boldest revelations involving his late uncle, John F. Kennedy Jr.
It is not every day that someone running for Congress is invited to comment on a family member’s romantic reputation, yet that is exactly what happened during a recent radio appearance.
While speaking on SiriusXM’s Radio Andy on Andy Cohen Live on Tuesday, June 9, the 33-year-old Democrat, who is running in New York’s 12th Congressional District, was asked about Madonna’s widely discussed remark that JFK Jr. was the greatest lover she had ever had.
The question came as Schlossberg was trying to talk about politics, family history and his campaign to replace longtime Democratic Rep. Jerry Nadler, who is retiring after more than three decades in Congress.
After laughing for a moment, Schlossberg gathered himself and came back with an answer that managed to be both cautious and playful.
“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.”
Host Andy Cohen appeared to appreciate the answer, and the moment quickly became one of the lighter viral clips from a race that has otherwise been dominated by endorsements, fundraising and questions about whether Schlossberg can turn his social media profile and Kennedy family name into actual votes.
Madonna originally made the comment while promoting her upcoming album Confessions II, taking part in a Q&A with Grindr alongside several celebrity guests. Before answering the question, she set a condition for herself.
“I’m only going to name dead people,” she said, before name dropping JFK Jr.
The exchange reportedly took place during a promotional video with a panel that included designer Raul Lopez, playwright Jeremy O. Harris, Bob the Drag Queen, dancer Ivy Mugler and Interview magazine’s Marcello Gutierrez.
Designer Raul Lopez immediately backed up the choice.
“Everyone says his d*** was crazy and he was a good f***,” he told Madonna.
Madonna suggested she had heard similar stories before.
“You’re the third person I’ve heard say that.” Madonna’s response was a simple “mmm hmm.”
The remark drew fresh attention to a brief but much-discussed link between Madonna and Kennedy Jr., whose private life has remained a subject of public fascination decades after his death.
She and Kennedy Jr. were briefly involved in the late 1980s, during a period when he was working as an assistant district attorney in Manhattan and she was at the height of her global fame. Christopher Anderson, who wrote The Day John Died, said Kennedy Jr. was:
“dazzled by the notion of dating Madonna”
and
“not above being star struck.”
One of Madonna’s dancer friends also reportedly offered a memorable observation about their chemistry.
“see it in his eyes that first time they met.”
The romance was short-lived. People close to Kennedy Jr. later described it as:
“totally a fling”
with physical attraction said to be the main driver rather than any lasting emotional connection.
There was also another complication at the time: Madonna was still married to Sean Penn, a detail that reportedly did not sit well with Kennedy Jr.’s mother, Jacqueline Kennedy Onassis. Madonna and Penn divorced in 1989.
Kennedy Jr. later married Carolyn Bessette in 1996. He died on July 16, 1999, when the plane he was piloting crashed into the Atlantic Ocean near Martha’s Vineyard. Carolyn Bessette-Kennedy and her sister, Lauren Bessette, also died in the crash.
He was 38.
For anyone less familiar with Schlossberg, his full name is John Bouvier Kennedy Schlossberg. He is the only grandson of President John F. Kennedy and Jackie Kennedy Onassis, and the son of former US Ambassador Caroline Kennedy and designer Edwin Schlossberg.
Born in 1993, he first built a public profile through social media, political commentary and appearances at Democratic events before entering the 2026 midterm race.
He announced his campaign for New York’s 12th Congressional District in November 2025 after Nadler said he would not seek another term. The district covers a heavily Democratic slice of Manhattan, including much of the Upper West Side, Upper East Side and Midtown.
He is campaigning in New York’s 12th Congressional District under the slogan:
“Believe in something again”
His campaign website presents him as a younger-generation Democrat focused on government transparency, affordability, housing, public safety, campaign finance reform, healthcare, education, immigration, climate policy, LGBTQ+ rights and standing up to President Donald Trump.
His platform includes anti-corruption measures, a tax deduction for renters, and an expanded federal Nurse Corps. He has also proposed a monthly benefit for parents that he has called a “Monthly Mom’s bonus,” and has said he will not take Super PAC money, corporate PAC money or money from big AI companies.
Schlossberg has some high-profile help: former House Speaker Nancy Pelosi endorsed him earlier in the race. But the primary is competitive, and he is running against other prominent Democrats including New York assemblymen Micah Lasher and Alex Bores, attorney George Conway and Nina Schwalbe.
Lasher, a former Nadler aide, has been endorsed by Nadler and New York Gov. Kathy Hochul, adding to the pressure on Schlossberg to prove that name recognition alone will not be enough.
The Democratic primary is scheduled for June 23, 2026, with the nominee expected to be heavily favored in the general election because of the district’s Democratic lean.
If elected, Schlossberg would become the first direct descendant of JFK to win elected office. Before that, however, he must get through a crowded primary and persuade voters that his campaign is more than another chapter in the Kennedy story.
Whether his light-hearted defense of his uncle’s reputation helps or hurts him politically is unclear. What is certain is that it produced one of the more unexpected moments of the campaign so far.