Jack Schlossberg, grandson of the iconic Jacqueline Kennedy Onassis, has sparked outrage with a peculiar Instagram post that seems to mock his late grandmother’s personal struggles.

According to Daily Mail, Schlossberg, 32, posted a video on Monday while shopping, zooming in on a People magazine cover featuring Jackie and John F. Kennedy with the headline "Jackie Knew Everything." He captioned it in all-caps, "Jackie was right about everything," seemingly making light of claims that Jackie confronted JFK over rumors of an affair with Marilyn Monroe, a situation that reportedly caused her deep distress.

The magazine’s August cover story revisits the painful speculation surrounding JFK’s alleged infidelity, noting Jackie’s expressed worry over the rumors. Schlossberg’s flippant tone in addressing such a sensitive family matter has raised eyebrows, especially given Jackie’s enduring reputation as a dignified and discreet First Lady until her passing from cancer in 1994 at age 64.

Family Tensions and Public Missteps

Schlossberg’s social media antics are not an isolated incident; they follow a pattern of controversial behavior that appears to have distanced him from the Kennedy clan. His absence from the family’s annual Fourth of July celebration at Hyannis Port, alongside estranged relative Robert F. Kennedy Jr., suggests a growing rift.

While a video posted by Kerry Kennedy showed dozens of family members gathered in patriotic spirit, Schlossberg was conspicuously missing, despite claims from Victoria Kennedy, Ted Kennedy’s wife, that all were invited. Some speculate that his recent actions, including this Instagram post, have positioned him as the newest family outlier.

Adding to the concern, Schlossberg, who graduated from Harvard Law School in 2022, has struggled to establish a stable career path despite his prestigious background. A brief stint as a political correspondent for US Vogue yielded little of note, and he has not contributed to the magazine since last fall.

Online Outbursts Raise Eyebrows

Beyond family matters, Schlossberg’s online behavior has drawn criticism for its crude and erratic nature. A recent deleted comment targeting journalist Megyn Kelly with a sexually explicit remark, later screenshot and shared widely, underscored his tendency to lash out publicly.

Kelly, who previously called Schlossberg “despicable,” has not commented on this latest incident, though it follows a February episode where he deleted all social media accounts after a tirade against her views on transgender issues. Critics at the time suggested he was experiencing a breakdown, a perception reinforced by subsequent attacks on Daily Mail columnist Maureen Callahan with vulgar language.

Schlossberg has also repeatedly targeted his cousin, RFK Jr., with harsh labels and even a bizarre challenge to a one-on-one confrontation in an April post. Such actions clash with his self-proclaimed image as a progressive “true Democrat,” leading many to view him as more of an internet provocateur than a serious voice.

A Legacy at Odds with Actions

Jacqueline Kennedy Onassis remains a symbol of grace, style, and resilience, making Schlossberg’s apparent disregard for her private pain all the more jarring. As the son of Caroline Kennedy, Jackie’s only daughter, his actions reflect not just on himself but on a family long under public scrutiny.

His checkered history, from employment struggles to public feuds, paints a picture of a young man grappling with the weight of an extraordinary legacy. While his education and connections—his father is renowned designer Edwin Schlossberg—offer immense opportunity, his choices continue to perplex observers.

Schlossberg’s latest Instagram post is not just a jab at family history but a reminder of how personal struggles can play out in the digital age. It’s a stark contrast to the discretion his grandmother embodied, even amid the Kennedy family’s well-documented scandals.

Navigating Privilege and Responsibility

In a time when social media amplifies every misstep, Schlossberg’s behavior raises questions about the balance between personal expression and familial responsibility. For conservatives wary of progressive excesses, his antics might seem like a cautionary tale of unchecked privilege in elite circles.

Yet, there’s room for empathy—navigating the shadow of a name like Kennedy can’t be easy, especially under constant public gaze. Still, one wonders if a bit more restraint could help Schlossberg reclaim some of the dignity associated with his grandmother’s legacy.

Ultimately, this episode is less about Jackie’s past and more about Jack’s present, as he wrestles with a path that seems increasingly at odds with the values of decorum and respect his family once epitomized. For now, the nation watches, hoping this wayward grandson finds a way to honor rather than undermine a storied heritage.