Jack Schlossberg, the thirty-three-year-old New York congressional candidate and nephew of the late John F. Kennedy Jr., recently made headlines after sitting down with Andy Cohen and John Hill for an episode of SiriusXM‘s Andy Cohen Live. Cohen, fifty-eight, wasted no time bringing up Madonna’s recent revelation, in which the sixty-seven-year-old pop star named JFK Jr. as the best sex she ever had. Schlossberg stuttered before responding. “I’m running for office,” he said, before adding,
“All I can say is that I bet she was right.”
As per a report shared by SiriusXM, Madonna had made the admission in a video for the gay dating app Grindr, shot to celebrate her upcoming Confessions II album. She was joined by Ivy Mugler, Raul Lopez, Jeremy O. Harris, Bob the Drag Queen and Marcelo Gutierrez. The group was asked a series of intimate questions, covering everything from sexy photos to whether size matters.
When asked about the best sex of her life, Madonna said she would only name dead people, before whispering JFK Jr.’s name. Gutierrez chimed in, saying he had heard the same rave reviews about JFK Jr., to which Madonna replied,
“So you know it’s true.”
Jack Schlossberg opens up about Kennedy family heirlooms and JFK Jr.’s lost belongings:
As per a report shared by People, Cohen also turned the conversation toward Kennedy family heirlooms, asking Schlossberg whether he had a favourite. Schlossberg was quick to show off what he was already wearing.
“This is my favorite tie. It’s [my grandfather] JFK’s tie. I wear it for good luck and today was a big day for me because I am with Andy Cohen. That’s the coolest,” Schlossberg said.
“I have five ties. I only wear five ties ever. This is one of them,” he added.
Cohen then wondered whether Jack Schlossberg had inherited anything from his late uncle JFK Jr., whose style is having a moment right now thanks to FX’s hit series Love Story, a dramatised retelling of JFK Jr.’s romance with Carolyn Bessette Kennedy.
Schlossberg’s answer was candid, if a little surprising.
“I have, like, a watch that doesn’t work,” he said.
“He lost most of his clothes apparently. He was given a lot of JFK heirlooms and I think he lost them all,” he added.
Jack Schlossberg opens up about his congressional run and the state of the Democratic Party:
As per a report shared by Vanity Fair in May 2026, the magazine sat down with Schlossberg as his Manhattan congressional run was picking up steam. Vanity Fair came to him with the observation that Democrats are in the middle of a rough patch.
“Okay, so I’m gonna, I’m gonna get ready by putting on my hat, because you just mentioned the Democratic Party not knowing what it’s doing. This is my solution. It’s ‘Believe in Something Again.’ That’s our campaign slogan. #BISA. BISA Nation,” he said.
Jack Schlossberg went on to explain what drives the message, pointing to America’s 250th birthday and the stretch of Manhattan he is running in, which goes from 96th to 14th Street.
“Believe in something again. I think a privilege that I have, that we all share, is a connection to our past. This is our country’s 250th birthday, and the district I’m running in…there are monuments to generations that built this country that believed in America. And right now, people don’t believe in anything anymore. You can’t believe what the president says,” he shared.
Jack Schlossberg didn’t stop there.
“We’re at war. We have no idea what’s going on. People don’t feel like their vote matters,” Schlossberg added.
Edited by Ryan D’souza