Jack Schlossberg, the grandson of the late President John F. Kennedy, has stirred conversation with a pointed social media post during his family's holiday celebrations. The 32-year-old congressional candidate shared images of himself reading a book critiquing materialism while surrounded by the trappings of immense wealth.
A Holiday Post with a Political Message
On Thursday, Schlossberg posted a carousel of images to his Instagram account, which boasts over 800,000 followers. The photos offered a glimpse into the Kennedy family's Christmas gathering. In one striking snapshot, he is seen lounging before a fireplace, engrossed in a copy of Michael Lerner's 1992 anthology 'Tikkun...to Heal, Repair and Transform the World'.
The book is a collection of writings that address what Lerner describes as the 'materialism, anti-intellectualism, conservatism and spiritual deadness' within some parts of the organised Jewish community. Schlossberg, who was raised Catholic but identifies as culturally Jewish through his father, captioned the post: 'I love my family,' before adding, 'Tikkun olam is a powerful concept in the Jewish tradition — improve the world!'
The phrase 'Tikkun Olam,' meaning 'repair of the world,' is a core Jewish concept centred on social justice and ethical living. The post's irony was underscored by another image featuring an embroidered pillow that read: 'If you met my family, you'd understand.' The Kennedy family fortune was last publicly estimated by Forbes at approximately $1.2 billion in 2015.
The Congressional Campaign and Controversial Persona
This holiday activity comes as Schlossberg is mounting a serious campaign for Congress. He announced his candidacy last month for New York's solidly Democratic 12th Congressional District, aiming to replace the retiring Jerry Nadler in the 2026 midterm elections.
In his campaign launch, he attacked the White House and highlighted a 'crisis at every level,' pointing to cuts in education, healthcare, and social programmes. Seen as a progressive on the left flank of the Democratic Party, he has backed figures like democratic socialist Zohran Mamdani and called for the party to change.
However, his path is crowded. He faces competitors including two state assembly members, a city council member, and Parkland school shooting survivor Cameron Kasky. Prediction market site Kalshi currently gives him a 30 percent chance of winning the seat.
Schlossberg has cultivated a provocative online persona, frequently attacking former President Donald Trump and his cousin, Robert F. Kennedy Jr., whom he has mocked for his spasmodic dysphonia and vaccine scepticism. These antics have led to controversy, including a brief social media hiatus after he falsely accused lawyer Alan Dershowitz of killing his wife.
Family, Future, and Political Legacy
Other holiday posts included a light-hearted video of Schlossberg wearing his campaign shirt and trying to crack a chestnut, jokingly captioned 'next year I'll be at my in-laws'—a nod to his current single status. In a recent New York Times profile, he revealed he hopes for a wife and children 'one day.'
Despite the recent departure of his campaign manager, Annabel Lassally, his team remains confident. A campaign spokesperson stated: 'We continue to grow post-launch as the only campaign focused on local issues and progressive policy... It's all systems go!' His staff has touted his social media savvy as a key asset to break through a crowded field, even defending some of his more unconventional online behaviour.
As a graduate of Harvard and Yale, and the son of Caroline Kennedy, Schlossberg is attempting to carve his own political path while invoking the legacy of his grandfather, whom he sees as a role model. His holiday reading choice, juxtaposed with his environment, presents a complex portrait of a modern political heir seeking office in a time of profound economic disparity.
