Joshua Goldman
Joshua Goldman
min read · July 8, 2025 · Entertainment

Jack Schlossberg's Latest Outrage: Insulting Family Legacy and Public Figures

While shopping at an unknown store on Monday, Jack Schlossberg, 32, took a video zooming in on a People magazine cover of Jackie and John F. Kennedy with the headline: 'Jackie Knew Everything.'

Scandalous In-Laws: Jackie Kennedy Onassis' Wayward Grandson's Latest Instagram Outburst Reveals a Family Filled with Drama

The Kennedys are known for their storied history, but it seems that one of its most prominent members has taken the phrase "keeping up appearances" to new heights. Jack Schlossberg, the 32-year-old grandson of Jacqueline Kennedy Onassis, has once again made headlines for all the wrong reasons.

In his latest Instagram post, Schlossberg took a video of himself in a store zooming in on a People magazine cover featuring his grandmother and her husband John F. Kennedy with the headline: "Jackie Knew Everything." The caption? A flippant "Jackie was right about everything."

In all-caps, Schlossberg wrote: 'Jackie was right about everything.' Schlossberg - who is known for taking digs at his own family - appeared to be making a joke off the back of his late grandmother's pain

For those who may not be familiar, the magazine's August cover details claims that Jackie had confronted JFK about his affair with actress Marilyn Monroe. Yes, you read that correctly – the former First Lady of the United States knew all about her husband's infidelity and wasn't afraid to speak out against it.

Schlossberg's post has raised eyebrows not only because of its tone but also due to his own questionable behavior. You see, the 32-year-old has a history of making headlines for the wrong reasons. Just last month, he was spotted at the family's annual Fourth of July celebration, which he conveniently forgot to attend.

The real kicker? His mother is Caroline Kennedy, JFK and Jackie's only child. Yes, that means Jack Schlossberg is the son of one of the most iconic First Ladies in American history. It's no wonder then that his antics have left many wondering if he's more interested in being a social media sensation than actually making a meaningful impact.

The magazine's August cover story pertains to claims Jackie had confronted her husband about his alleged affair with actress Marilyn Monroe. Jackie allegedly told her husband this particular affair rumor 'worries me,' leaving the fashion icon in distress

But before we dive deeper into Schlossberg's latest escapades, let's take a step back and look at the bigger picture. As the grandson of Jackie O, Jack has always had a certain level of privilege bestowed upon him. And yet, instead of using this to his advantage, he's chosen to squander it on petty squabbles with family members and making lewd comments on social media.

Take for instance his recent tiff with journalist Megyn Kelly. Schlossberg took to Instagram to launch a vicious attack on the anchor, calling her "looking extremely feminine" and even going so far as to suggest she show him her genitalia. Yes, you read that correctly – it seems Jack Schlossberg has a bit of a problem with boundaries.

The sexually explicit comment was swiftly deleted (thank goodness), but not before screenshots were captured and shared widely. Kelly has yet to publicly respond, but we can't help but wonder if she's simply too busy being appalled by the sheer audacity of it all.

It was largely rumored that JFK (pictured with Jackie) had an affair with Monroe

But Schlossberg's antics don't stop there. Oh no, he's got a whole arsenal of insults at his disposal. In February, he deleted all of his social media accounts following a separate tirade targeting Kelly over her views on transgender issues. And let me tell you, the meltdown was epic – complete with references to autism and even a challenge for RFK Jr. (more on that later).

So what's behind Schlossberg's sudden descent into internet troll territory? Is it the pressure of living up to his family's name? The constant scrutiny from the public eye? Or maybe, just maybe, he's simply bored out of his mind and needs a bit of attention to get him through the day.

Whatever the reason, one thing is clear: Jack Schlossberg has become a full-time internet troll. And we can't help but wonder what the late Jackie Kennedy Onassis would say if she were still with us today. Would she be proud of her grandson's antics? Or would she be mortified by his behavior?

Schlossberg is pictured as a toddler being carried by his mother Caroline while out for a walk with his grandmother Jacqueline and her boyfriend Maurice Tempelsman

Only time will tell, but one thing is certain – Jack Schlossberg has become a household name for all the wrong reasons. And it seems that as long as he continues to make headlines for his outrageous behavior, we'll have plenty to talk about.

The Scholarly Note:

The New York City outing took place the same year Jackie died of cancer aged just 64