Jack Schlossberg, the 32-year-old grandson of President John F. Kennedy, officially announced his candidacy for the U.S. House of Representatives on November 12, 2025, seeking the New York 12th Congressional District seat currently held by longtime Democrat Jerry Nadler. The announcement has sparked renewed interest in Schlossberg’s family connections to pop superstar Taylor Swift, stemming from his cousin’s brief but memorable 2012 romance with the global music icon.
In a campaign video posted across social media platforms, Schlossberg declared his intention to represent Manhattan’s Upper West Side and parts of Brooklyn. “This district should have a representative who can harness the creativity, energy and drive of this district and translate that into political power in Washington,” he stated in his announcement video. The campaign officially launched Wednesday, November 13, 2025.
The Swift-Kennedy Connection Revisited
Schlossberg’s congressional announcement has reignited public curiosity about his family’s connection to Taylor Swift, who dated his second cousin Conor Kennedy during the summer of 2012. Swift dated Conor Kennedy, Robert F. Kennedy Jr.’s son, in a relationship that ended in October 2012 . The romance, though brief at just three months, left a lasting cultural impact and produced musical inspiration for Swift’s work.
During that relationship, Swift wrote the song “Starlight” about Conor’s grandparents, Ethel Kennedy and Robert F. Kennedy, and performed it personally for Ethel Kennedy, who praised Swift as “sensational, inside and out” . The Kennedy family matriarch noted Swift’s adventurous spirit, saying she was “game” for new experiences like sailing and participated enthusiastically in family activities.
In a recent New York Times profile accompanying his campaign announcement, Schlossberg addressed persistent questions about whether he harbored any jealousy regarding his cousin’s high-profile relationship. When asked to confirm or deny “As a teenager, you were jealous when your cousin Conor Kennedy dated Taylor Swift,” Schlossberg responded with a clear “Deny” .
Political Rise and Social Media Strategy
Schlossberg has built a significant online following through his unique approach to political commentary, combining humor with serious Democratic messaging. As Vogue’s political correspondent and a vocal supporter of Democratic causes, he has positioned himself as a fresh voice in American politics, particularly appealing to younger demographics.
The Kennedy heir has been particularly critical of his controversial relative Robert F. Kennedy Jr., who recently became health secretary under President Trump. Schlossberg has consistently opposed RFK Jr.’s anti-vaccination stance and conspiracy theories, using social media platforms to counter his cousin’s messaging with fact-based content.
His political engagement extends beyond social media. Schlossberg previously endorsed Joe Biden and Kamala Harris in their respective campaigns and spoke at the Democratic National Convention, establishing himself as a legitimate political voice within the Kennedy legacy.
Swift Support Speculation
Following Schlossberg’s congressional announcement, political observers immediately began speculating about potential celebrity endorsements, particularly from Taylor Swift. Social media users started wondering whether Taylor Swift, a Democrat-leaning celebrity who previously supported Kamala Harris against Republican Donald Trump, would support Jack Schlossberg .
Swift’s political activism has become increasingly prominent in recent years, with her endorsement of Democratic candidates carrying significant weight among her millions of fans. Her support for Vice President Kamala Harris in the 2024 election cycle demonstrated her willingness to engage in high-profile political races.
However, there are no reports that suggest Taylor Swift is supporting Jack Schlossberg at this time. Neither Swift’s representatives nor Schlossberg’s campaign team have made any statements regarding potential endorsements or campaign involvement.
Family Legacy and Political Aspirations
As the only grandson of JFK and son of former Ambassador Caroline Kennedy, Schlossberg carries the weight of one of America’s most iconic political dynasties. His entry into electoral politics represents a new generation of Kennedy leadership, though his approach differs markedly from traditional political campaigns.
Schlossberg’s candidacy comes at a crucial time for Democratic Party outreach to younger voters, a demographic where the party underperformed in recent elections. His viral social media presence and unconventional political messaging style have already attracted significant Gen-Z engagement, potentially offering Democrats a blueprint for future campaigns.
The Manhattan district Schlossberg seeks to represent includes some of the most culturally influential neighborhoods in America, from the Upper West Side’s intellectual community to Brooklyn’s creative enclaves. His campaign messaging emphasizes harnessing this creative energy for political change in Washington.
Campaign Focus and Democratic Vision
Beyond celebrity connections and family legacy, Schlossberg’s campaign centers on traditional Democratic priorities including civil rights, public service values, and social welfare programs. He has been particularly vocal about what he describes as the potential for a “constitutional crisis” under another Trump administration.
His background includes Harvard Law School graduation and extensive work in political commentary, positioning him as both an insider to Washington politics and an outsider to traditional campaigning. The combination of Kennedy name recognition with modern social media savvy represents a unique approach to contemporary Democratic politics.
Schlossberg’s criticism of Trump administration policies, particularly those involving his relative RFK Jr., demonstrates his willingness to challenge both political opponents and family members when principles are at stake. This independence may prove crucial in establishing his own political identity separate from both Kennedy legacy and celebrity associations.
Frequently Asked Questions
Did Taylor Swift ever date Jack Schlossberg?
No, Taylor Swift never dated Jack Schlossberg. Swift briefly dated Jack’s second cousin, Conor Kennedy, during the summer of 2012. Jack Schlossberg has explicitly denied ever being jealous of this relationship.
Is Taylor Swift supporting Jack Schlossberg’s congressional campaign?
There are currently no reports or official statements indicating that Taylor Swift is supporting Jack Schlossberg’s congressional campaign, despite speculation on social media following his announcement.
What is Jack Schlossberg’s relationship to the Kennedy family?
Jack Schlossberg is the grandson of President John F. Kennedy and the son of former Ambassador Caroline Kennedy. He is running for the U.S. House of Representatives in New York’s 12th Congressional District.
When did Jack Schlossberg announce his congressional campaign?
Jack Schlossberg announced his candidacy for Congress on November 12, 2025, with his campaign officially launching on November 13, 2025.
What political positions does Jack Schlossberg support?
Schlossberg is a Democrat who supports civil rights, public service values, and social welfare programs. He has been particularly critical of Trump administration policies and his relative RFK Jr.’s controversial positions.