After years of commenting on politics, CNN weekend anchor John Avlon, a self-proclaimed "centrist," decided to, in his words, "step up and get off the sidelines." In February, the former Rudy Giuliani speechwriter announced that he was running as a Democrat to unseat Republican representative Nick LaLota in New York's First Congressional District, located in eastern Long Island.
Lest anyone accuse Avlon of carpetbagging—a charge leveled by some of the Democratic primary opponents he defeated last month—Avlon quickly made it known that the Hamptons village of Sag Harbor has been his family's primary residence for years.
"We've lived there since 2009," Avlon told a local news outlet earlier this month, adding that he and his wife, Firing Line host Margaret Hoover, had "voted there for years."
Avlon's claims to be a long-term, primary resident of New York's first district are provably false, according to a Washington Free Beacon review of myriad publicly available records. Instead, Avlon's primary residence was a three-hour drive away, in Manhattan, at least through 2023. He has not sold his multimillion-dollar Manhattan apartment, and in 2023 he collected a tax credit on it as his primary residence.
Indeed, there is no evidence that Avlon or any member of his immediate family lived in Long Island full-time until this year at the earliest, nor that his family owned a home there until 2017. In fact, there are multiple indications that Avlon was a full-time resident of Manhattan until he announced his congressional bid.
It's a touchy subject on Long Island's East End. Avlon is running to be the sole congressman representing the Hamptons, one of the country's most expensive zip codes, where Manhattan's captains of finance have weekend homes.
For decades, the Hamptons' congressional representative has been a tribune for the working class, year-round residents who form the East End's service class. LaLota and his fellow Republican predecessor, Lee Zeldin, were born and raised on Long Island and made their careers there before running for office. Avlon, the third-generation scion of a Manhattan real estate dynasty, would represent the wealthy weekenders, many of them political liberals, who have long been resented by the more conservative locals.
Avlon's claim to have lived full-time in the Hamptons is even stranger when one considers his career in media—from editor in chief of the beleaguered Daily Beast to weekend anchor on CNN—over the last 15 years. Every job Avlon has had since he got his MBA at Columbia University (in Manhattan) was based in New York City and required in-office work. Avlon did not resign from his post as a weekend anchor at CNN, where he appeared frequently from CNN's midtown studios on weekdays as well as weekends, until February of this year.
Before his pivot to liberal media outlets like CNN and the Daily Beast, Avlon was a fixture of conservative politics in Manhattan. He started at City Hall, working for Giuliani, before moving to the Manhattan Institute, a Midtown-based think tank.
Such jobs likely explain why he purchased a $3.4 million Manhattan co-op in the exclusive Gramercy Park neighborhood with his wife in 2015, six years after he claims he moved to Long Island, public records show. Avlon and Hoover still own that apartment, located less than 30 minutes away by subway to CNN's studios but a nearly 3-hour drive from the former whaling village of Sag Harbor.
At the time, Sag Harbor, where Avlon and Hoover had yet to buy a home, was, in Hoover's words, a "cozy retreat." In a 2015 essay for Modern Luxury magazine, she wrote fondly of their Long Island vacations and said the pair hoped "to one day make Sag Harbor our permanent escape from the busy city."
Avlon's race is considered critical for Democrats' hopes to flip control of the House. LaLota, the freshman incumbent, comfortably won the seat by a 10-point margin in 2022. Redistricting has made the district potentially more competitive, although independent election analysts say LaLota remains the favorite.
Avlon's chances may turn more difficult should voters there find out that he did not purchase his seven-figure Hamptons home—through an LLC registered at his Manhattan apartment—until 2017. There are no public records of him owning a home in the town before that time.
LaLota, a Navy veteran who was deployed overseas three times, has deep Long Island roots. The son of a Nassau County police officer, LaLota served on the board of the Amityville Board of Trustees and worked as chief of staff to the Suffolk County Legislature after discharging from the Navy.
His humble background contrasts with that of Avlon, who attended the elite boarding school Milton Academy, in Massachusetts, and Yale, in Connecticut, like his father before him. Avlon now oversees a large investment portfolio, much of which is in a trust in his mother's maiden name, public financial disclosure documents show.
The Avlon family was a major player in New York real estate. Avlon's father represented the Greek shipping family that owned the historic Mayflower Hotel, which, when it was sold in 2004 and slated for demolition, was "considered by many developers one of the most valuable sites in Manhattan," according to the New York Times. The Avlons now have the locus of their business in Charleston, S.C., where they own an historic home near the water. They appear to still have real estate interests in New York, Florida, and Texas. It's not clear how involved John Avlon is in the family business.
LaLota's public-sector salary was roughly $150,000 a year before he was elected, public filings show, whereas Avlon was paid $625,000 a year by CNN during the less-than-three-year period he worked there. Previously, his income in journalism and politics was likely more modest (the New York Post recently reported that the Daily Beast editor in chief job pays $300,000 a year), although Avlon and Hoover's investments likely helped finance their purchases of the $3.4 million apartment.
In recent years, Avlon also collected upwards of $25,000 a pop to give speeches at organizations such as the Rancho Mirage Writers Festival. His alma mater, Milton, paid him $5,000 to deliver a commencement address.
A spokesman for the Avlon campaign did not answer a long list of questions about the candidate's residency history, or whether he still takes advantage of a tax rebate for Manhattan residents. Instead, the spokesman stopped short offering an exact year of when Avlon's family moved to the Hamptons and said that "John and his family took the census and voted in Sag Harbor in 2020," 11 years after Avlon claimed he moved to the East End. His campaign declined to provide evidence that he has voted there since 2020.
Before his run for Congress, Avlon took great pride in his Gramercy dwelling. In 2018, a year after the family bought their Hamptons getaway, the apartment was prominently featured in a Times profile about Avlon's marriage to Hoover.
"Their duplex apartment, part of a house once owned by Robert Winthrop Chanler, an Astor, artist and early-20th-century bon vivant, is traditionally decorated," the profile's author wrote. The couple were photographed sitting outside in their apartment's small yard, a Manhattan rarity. There is no mention of Sag Harbor.
Avlon and Hoover's children lived in the apartment at the time, the piece states.
Photos on Avlon's Instagram show he took his children trick-or-treating in Manhattan as recently as 2022. Last year, Avlon's Instagram suggests, the family celebrated Christmas in Gramercy Park.
Based on social media and publicly available records, the Avlon children appear to have attended, as recently as last year, an exclusive Downtown Manhattan private school known for educating the children of wealthy celebrities, many of whom own weekend Hamptons homes. A representative of the school did not reply to requests for comment, and Avlon's campaign did not answer a question about whether the children are still enrolled at the school.