It was a hot August day, and the patrons of 75 Main in Southampton were trying to figure out who on earth was the man wandering up and down Main Street cosseted by several armed security guards.
The VIP, it turned out, was Bruce Blakeman, the Republican candidate challenging Kathy Hochul in the New York gubernatorial race, and like so many politicians and presidential hopefuls this time of year, he had ventured out to the Hamptons for a fundraiser. (The following weekend, Hochul herself would make the trip to 75 Main for a bipartisan breakfast hosted by billionaire supermarket tycoon John Catsimatidis.) This Friday, Blakeman will campaign with President Donald Trump before attending a fundraiser with Steve Witkoff, Trump’s Middle East envoy.
This is what August looks like in an election year out on the East End of Long Island. “Ever since the Bill Clinton days, all the politicians come because that’s where the money is,” Catsimatidis tells Vanity Fair. The Hamptons and the ritzy Massachusetts islands to its northeast—Martha’s Vineyard and Nantucket—become a landing ground for political candidates, who parachute in to raise money for their midterm races and test appetites for their presidential ambitions.
“I can’t walk down the street without running into a member of Congress,” says one political fundraiser with a home in Nantucket.
For pols with national profiles, the trip is well worth it. It’s an opportunity for aspiring presidents to meet would-be donors amid the murmuring shade of perfectly manicured hedgerows, and a chance for the wealthy who blow ungodly sums on second-home landscaping to make good on their investment by flexing (and gaining) some clout in Washington.
A series of candidates in the conversation for 2028 have so far made the pilgrimage to America’s summer money meccas. Maryland governor Wes Moore stopped by a Westhampton synagogue on a fundraising swing last month. Pennsylvania governor Josh Shapiro made the trip to the South Fork as well, while Illinois governor JB Pritzker spoke to supporters at the home of a Broadway producer in Sagaponack. Senator Jon Ossoff of Georgia is doing his own swing the weekend of August 22 for a lunch at the East Hampton home of jewelry designer Brooke Neidich followed by a fundraiser at the Water Mill estate of Alex Soros and Huma Abedin.
Book signing for Hillary Clinton at BookHampton in East HamptonSonia Moskowitz/Getty Images
The trips are ostensibly opportunities to rake in cash from big-dollar donors for the midterm elections, but they often serve an implicit, longer-term purpose as well: building out a national fundraising network to support a future campaign for president. In 2006, Hillary Clinton stopped by East Hampton for a fundraiser billed as backing her Senate campaign, though at the time she led the polls for president. Her Senate fundraising operation ultimately left her with a $13 million war chest she could convert into funding for a presidential run. This strategy wasn’t without costs for Clinton: The New York Times published a bruising account in 2016 of her “ultrarich” fundraising circuit, which included dancing alongside Jimmy Buffett, Jon Bon Jovi, and Paul McCartney at a $33,400-a-head garden party in Sag Harbor.
