Photo Illustration by Erin O’Flynn/The Daily Beast/Getty and Wikimedia Commons
It has all the markings of a small-town standoff: a property dispute, a wealthy newcomer, bureaucratic dysfunction, 19th century law, and an army of furious dog owners. But Winnetka, Illinois, where this battle is unfolding, is no podunk community. Here, the median owner-occupied house is worth over $1.1 million, and along Lake Michigan, the nexus of the controversy, large estates can pull in 10 times that.
The cast of characters in the saga includes officials on the Winnetka Park District Board of Commissioners—the bureaucrats—and a private equity billionaire, Justin Ishbia, who has snapped up four lakefront properties since 2020.
The tricky bit: one of those houses is sandwiched by two public parks. Around the start of his buying spree, Ishbia agreed to swap that home and its accompanying private beach with the park district in exchange for an equal amount of land to the south—creating a mega-estate for himself and a mega-park for locals.