Jack Schlossberg, the grandson of the late President John F. Kennedy, has shared his candid reaction to revelations about his uncle, John F. Kennedy Jr.’s, past romantic encounters. Speaking on Andy Cohen’s radio show, Schlossberg didn’t shy away from the salacious details, particularly those involving pop icon Madonna.

When pressed by Cohen about whether he “chuckles” at Madonna’s assertion that JFK Jr. was “the best s– I ever had,” Schlossberg, who is currently running for political office, offered a wry but politically astute response. “I’m running for office,” he stated. “All I can say is that I bet she was right.” This response deftly sidesteps a direct endorsement while acknowledging the boldness of Madonna’s claim.
A Tragic Legacy: The Life and Loss of John F. Kennedy Jr.

John F. Kennedy Jr.’s life was tragically cut short in July 1999 when the plane he was piloting crashed, claiming the lives of his wife, Carolyn Bessette Kennedy, and her sister, Lauren Bessette. His death sent shockwaves across the nation, mourning the loss of a prominent figure and a symbol of a hopeful future.
Madonna, the Queen of Pop, recently made headlines by disclosing her past intimate relationship with Kennedy Jr. during a video for the LGBTQ dating app Grindr. As part of a discussion with fellow guests about their most memorable romantic encounters, Madonna, who is 67, chose to only name deceased individuals. She then whispered, “John Kennedy Jr.,” confirming a fling with the George magazine founder during the 1980s.
Cherished Heirlooms and Family Ties

Beyond the sensational revelations, Schlossberg also opened up about his connection to his grandfather, John F. Kennedy, and his uncle. During his conversation with Andy Cohen, the topic turned to family heirlooms. Schlossberg revealed his fondness for a particular tie, stating, “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.” He elaborated that he owns only five such ties, meticulously chosen for their significance.
Schlossberg also shared a poignant detail about possessing one of his uncle’s belongings: “I have, like, a watch that doesn’t work.” He admitted that John F. Kennedy Jr. apparently lost most of his clothing, despite inheriting many heirlooms from their grandfather. This suggests a sense of personal history and perhaps a less formal approach to preserving memorabilia within that branch of the family.
Critiques of Fictional Portrayals

The life and marriage of John F. Kennedy Jr. were recently explored in the FX miniseries “Love Story.” The show depicted Carolyn Bessette Kennedy through the performance of Sarah Paulson, while Paul Anthony Kelly portrayed the journalist.
However, Jack Schlossberg has been vocal in his criticism of such dramatised accounts. In March, he strongly condemned the miniseries and its producer, Ryan Murphy, in comments to CBS. “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 asserted. He further expressed his disappointment, stating, “If you want to know someone who’s never met anyone in my family, knows nothing about us, talk to Ryan Murphy. 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.” Schlossberg’s stance highlights a clear desire to protect his family’s legacy from what he perceives as inaccurate and exploitative portrayals.






