JFK Grandson Jack Schlossberg’s Bizarre Anti-Bobby Videos Backfire

By Nikos Biggs-Chiropolos, The Kennedy Beacon

Disagreements among the Kennedy family over Robert F. Kennedy Jr.'s presidential candidacy have received ample media coverage in the past year, including in The Kennedy Beacon. Many, but not all members of the family have supported this campaign, and Kennedy himself has said that he respects his family members – there are over 100 cousins and siblings – who may have different opinions. 

A few of his siblings and cousins have endorsed Biden and have gone to great lengths to attempt to disconnect RFK Jr. from his namesake’s legacy. But the worst offender has been Jack Schlossberg, the only grandson of President John F. Kennedy and the son of US ambassador to Australia, Caroline Kennedy, RFK Jr.’s first cousin.

Schlossberg’s numerous video rants against RFK Jr. on social media are so egregious that on May 9, The Hill’s Rising did an entire segment about his nasty attitude and unkindness toward his second cousin, and the vacuous nature of his own political values, when compared to others of his age. 

Co-host Briahna Joy Gray said, “This is not some young, uninformed kiddish behavior. And in fact, if you look at what people in his generational cohort or younger are actually doing with their lives… many of them are standing arm to arm, they’re putting their lives, their jobs, their prospects on the line to try to prevent an ongoing genocide. And so he’s out of step with, I think, the mood of the country. He’s out of step with his generational cohort. And it really… it is bizarre. It is bizarre, I think, on a personal level to be saying things about a family member who I presume you’re gonna have to see at an upcoming event. Like the fact that they’re ‘roided up’ and that’s what’s motivating their politics.”

Specifically, Gray is referring to five videos that Schlossberg posted last week in which he assumed personas (with thick accents) of different types of American voters, some filmed while riding around in his car and playing to the camera by winking and flexing his biceps.

These videos portray many unflattering stereotypes of American voters. Some of them even seem, unintentionally, to make fun of Biden voters, as well as other Americans with less wealth and privilege than Schlossberg. 

In four videos, Schlossberg performs characters he invented who will not be voting for Kennedy. In one, he takes on the personality of "Anthony" (pronounced “Ant-ny”) from Long Island who criticizes Kennedy for wanting to cut the military budget, saying “you don’t got my vote!” As a Jewish man named Joshua, Schlossberg claims he will vote for Biden (while mentioning Caroline Kennedy’s marriage to “a Jewish man”) and he also rants about RFK Jr.’s support for bitcoin. Most surprisingly, this video ends with a hysterical-sounding question, “Who’s gonna protect my money?” As a southerner named Wade, Schlossberg says he will vote for Biden because he believes in “honor, integrity, decency, and just plain old patriotism.” And another member of the cast, “Jimmy” with an apparent Boston accent, talks about admiring the Kennedy family but claiming in reference to RFK Jr. “that new guy – the young guy’s a prick.” 

In the video pinned to the top of his Instagram page, Schlossberg assumes the accent of a Russian-American named “Vlad,” claiming he does plan to vote for Kennedy due to his apparent support for Russia and Vladimir Putin.

Although he graduated with a dual law and business degree from Harvard in 2022, after which he passed the New York state bar, Schlossberg’s Instagram account resembles that of a frat boy more than it does an aspiring lawyer. While posts on his account from a few years ago show him wearing suits at official functions, Schlossberg has recently posted videos of himself gritting his teeth as he attempts to rip open a coconut with his hands or dancing seductively in a parking lot. He has also introduced a new personality this week, a British man named “Reginald” who talks incoherently about Bidenomics.

Schlossberg has been rumored to have his own political ambitions for years, making comments that fueled speculation from Town & Country magazine as far back as 2017 about considering a career in public service. The Democratic Party seems to see him as a potential protégé as well, as he was given the opportunity to speak alongside his mother at the party’s 2020 convention in support of Joe Biden.

Whether Schlossberg is trying to score political points or simply grow his social media following is unclear. He now boasts 137,000 followers on Instagram, but given the lack of intellectual depth in his selfie videos and his less than stellar acting skills, his ability to grab attention is likely because of his mother’s maiden name and the media’s love for family feuds. If common sense prevails, then publicly trashing a family member online to gain attention will likely backfire.

Nikos Biggs-Chiropolos studied government at Georgetown University and interned for several Democratic elected officials and their campaigns, and other affiliated groups. He then earned a master’s degree in urban studies in France, where extremely strict COVID-19 lockdowns led to his political reawakening and inspired him to try to help fix the broken two-party system.