Winnetka, Illinois, has long been considered Chicago’s marquee suburb with hotel-size homes at the end of heated driveways and faux-French country houses overlooking Lake Michigan. Popular with big-brand CEOs and lawyers, and familiar to non-Winnetkans as the setting of Home Alone, Ferris Bueller’s Day Off, and nearly every John Hughes movie ever made, it is a place where titanic wealth meets midwestern folksiness.

Four years ago, at the height of the pandemic, a mystery buyer began acquiring mansions along Winnetka’s waterfront and knocking them down. One of the mansions was less than a decade old and featured an indoor basketball court and a movie theater. Another, whose previous residents included a plastic surgeon and the inventor of the retractable seat belt, had a distinguished architectural pedigree. All three had sat next to each other overlooking a beach known for its fine white sand and would become part of a gaping construction zone.

Soon, the nameless buyer’s plans to build a 68,000-square-foot Nantucket-style mansion — a home nearly the size of the White House — abutting the town’s beloved waterfront Centennial Park, became known, leading to his unmasking. But the buyer, a young private-equity mogul named Justin Ishbia, had even bigger ideas. Ishbia acquired a fourth mansion in the same strip of beach, which he hoped to trade to the town in exchange for a strip of public parkland next to his future compound. The battle over that exchange has turned, to the delight of Chicago newspaper readers, into a public, personal, and seemingly endless conflict among the megarich.

Ishbia is one of the richest men in Illinois, a co-owner of the Phoenix Suns, and someone with the clout and connections to get his way. Unlike some other Chicago billionaires, he was known as agreeable, easygoing, and nonpolitical. This was his first taste of controversy, and he had little reason to expect any. In seeking to obtain public land for private use, he was following the lead of a growing number of extremely wealthy Americans across the country, from the Hamptons and Nantucket to Malibu, Aspen, and Montana. Often, the locals have limited recourse to resist. In Winnetka, they had the wherewithal to put up a fight.

When Americans give up public land, they frequently do so via an arcane, little-scrutinized procedure called a land swap. Such exchanges, usually between the government and a private individual or corporation, have resulted in enormous fortunes for the private parties, while the government often receives less valuable land that it nonetheless wants for specific projects, such as road construction. One relatively well-known example: In the 1990s, the Yellowstone Club, a members-only ski resort in Big Sky, Montana, with a billionaire clientele, received thousands of acres of prime national forest, while the government got property that had recently been cut over by a timber company.

The swap proposed in Winnetka was smaller than most. Its origins lay in the 1968 closure of a psychiatric facility for the wealthy called North Shore Hospital, which overlooked the lake and had an unfortunate reputation for losing patients to drowning. It was razed and turned into a grassy esplanade called Centennial Park. A little further down the beachfront sat an even older esplanade called Elder Lane Park. Between them was an odd neighbor: 261 Sheridan Road, a gloomy stucco mansion standing alone against the water with green space on either side. 261 Sheridan was privately owned, but over the next several decades, it often sat empty, dividing what could have been a ten-acre park. Winnetka officials longed to acquire and demolish it but lacked the funds.

In 2020, Ishbia saw an opportunity. At a meeting with the Winnetka Park District, he stood next to the fence separating his property from Centennial Park and offered to buy the stucco house and give it to the people. There was a condition. In exchange for 261 Sheridan, he requested a 70-foot strip of Centennial so he could build a buffer against public intrusion.

“It seemed like a win-win scenario,” said Ishbia. “There was one house in the middle of this park that didn’t make a lot of sense, and I had a solution........

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