When you’re running for office, every word counts. Jack Schlossberg learned that lesson firsthand during a Tuesday, June 9 appearance on SiriusXM’s Radio Andy, when host Andy Cohen hit him with one of the most unexpected celebrity gossip questions imaginable.
The setup? Madonna had recently told everyone—via a Grindr interview promoting her album Confessions II—that John F. Kennedy Jr. was the best sex she’d ever had. Cohen asked the 33-year-old Schlossberg, who happens to be running for office, how he felt hearing the Material Girl say that about his late uncle.
What happened next was pure political instinct wrapped in humor. After a thoughtful pause, Schlossberg leaned in with a response that Cohen himself called perfect:“I’m running for office. All I can say is that, I bet she was right.”It was the kind of answer that walks a tightrope—charming enough to land as a good joke, self-aware enough to defuse any awkwardness, and just brazen enough to show he wasn’t going to be precious about the whole thing.
The comment stemmed from Madonna’s candid chat with fashion designer Raul Lopez, where she explained she’d only name dead people when discussing her best experiences.“I’m gonna only name dead people,”the 67-year-old singer said, before whispering“John Kennedy Jr.”Lopez wasn’t shocked, apparently—he’d already heard similar claims from others. Madonna and JFK Jr. briefly dated in the late 1980s while her marriage to Sean Penn was falling apart. They reconnected years later when he asked her to pose for his George magazine in 1996, the same year he married Carolyn Bessette-Kennedy.
The couple’s story has experienced a cultural resurgence thanks to Ryan Murphy’s FX limited series Love Story, which premiered earlier this year and reignited public fascination with JFK Jr. and Carolyn’s relationship. They died in a plane crash near Martha’s Vineyard in July 1999, three years after their wedding. It’s the kind of history that makes a casual radio question about Madonna unexpectedly loaded with context—and makes Schlossberg’s quick wit all the more impressive.
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Local Lawton
Local Lawton is a contributor to LocalBeat, covering local news and community stories.