Joshua Goldman
Joshua Goldman
min read · August 11, 2025 · Entertainment

Inside the Kennedy Family Drama: Cheryl Hines Slams Caroline and Jack's Online Controversies

Kennedy heir Jack Schlossberg has been slammed by his famous family member as self-obsessed and fame hungry

KENNEDY SHAME: Caroline's Son Jack Schlossberg's Bizarre Online Antics Raise Eyebrows

The Kennedy dynasty, once synonymous with elegance and refinement, has hit a new low with the erratic behavior of Caroline Kennedy's 32-year-old son, Jack Schlossberg. The young heir to the family fortune has been making headlines for all the wrong reasons, leaving fans and family members alike wondering what's behind his bizarre online antics.

Schlossberg, who has been dubbed "the black sheep" of the Kennedy family, has been taking to social media to build a name for himself, but instead, he's managed to embarrass his mother and aunt. Cheryl Hines, Caroline's first cousin through marriage, recently spoke out about Schlossberg's behavior in an interview with The Wall Street Journal, saying she was too afraid to even discuss the topic.

Cheryl Hines, who is married to Schlossberg's relative - Robert F. Kennedy JR , made the savage accusations to the Wall Street Journal

"I don't understand what's going on with him," Hines confessed. "Her son's behavior – I don't even want to say anything because anything I say, he'll think someone's talking about him and get excited."

Schlossberg has been making waves online with his outrageous demands and bizarre behavior. Last month, he asked conservative journalist Megyn Kelly to show him her private parts on social media, leaving many wondering if he was joking or seriously requesting something that would make anyone uncomfortable.

But Schlossberg's antics didn't stop there. He also mocked the late Jacqueline Kennedy Onassis, his grandmother, and took to social media to share "heartfelt" memories of his uncle John F. Kennedy Jr., which many found suspicious.

Hines openly discussed the behavior of Schlossberg, 32 - who is the only grandson of John F. Kennedy through his mother Caroline Kennedy (pictured with her son)

Schlossberg's behavior has been a subject of concern for family members, with his aunt, Caroline, remaining eerily quiet on the matter. However, Cheryl Hines' husband, Robert F. Kennedy Jr., who is married to Hines, has been at the center of Schlossberg's online rants.

In a bizarre exchange last week, Schlossberg goaded Hines and her husband over a post made by RFK Jr wishing his wife a happy anniversary. The message was simple: "What does she let you do on your birthday?" with no further context provided.

This isn't the first time Schlossberg has targeted his aunt's husband online. In the past, he's publicly shamed RFK Jr for his anti-vaccination stance, which has led to controversy within the family.

After briefly serving as Vogue's political correspondent last year, the Kennedy heir then seemingly began to focus more on producing content for his own social media

Schlossberg's Instagram feed is filled with seemingly innocuous posts about mangoes and his love for them. However, experts speculate that this may be a cry for help or attention. "He's trying to get a reaction from people," says a source close to the family. "It's like he's craving validation online."

When asked about Schlossberg's behavior, Caroline Kennedy refused to comment, leaving many wondering if she's embarrassed by her son's antics.

As for Schlossberg's motives, insiders say it may be a combination of factors, including his desire for attention and his complicated family dynamics. "He's trying to build a name for himself, but it's not working," says the source. "He's getting more attention for all the wrong reasons."

Schlossberg became especially heated online about Ryan Murphy's most recent project 'American Love Story', which focuses on the romance of John F. Kennedy Jr. and Carolyn Bessette-Kennedy (pictured together)

Schlossberg's behavior has sparked concern among Kennedy family members, with some even questioning whether he's fit to inherit the family legacy.

The question on everyone's mind is: what will happen next? Will Schlossberg continue down this path, or will his family intervene and try to salvage their reputation?

Only time will tell, but one thing is certain – Jack Schlossberg has single-handedly brought shame to the Kennedy dynasty once again.

Schlossberg's mother is Caroline Kennedy - the only daughter of Jackie and JFK - who was five years old when her father was assassinated in 1963