How LA’s richest man went from billions to bust

Subscribe to enjoy similar stories. In the late 1990s, Gary Winnick donated millions of dollars to the Los Angeles Zoo and rubbed elbows with President Bill Clinton. He would soon buy the most expensive home in the country.

The Long Island native and one-time protégé of the former junk-bond king Michael Milken had amassed an estimated $6.2 billion fortune, and the Los Angeles Business Journal ranked him the richest man in L.A. Global Crossing, a company he founded that promised to lay undersea fiber-optic cable around the world, made him a billionaire on paper in less than two years, a faster rise than Gilded Age oil baron John D. Rockefeller or Microsoft co-founder Bill Gates.

“He’s so rich that his longtime housekeeper, to whom he gave stock in a company he was starting, is now a millionaire herself," the Los Angeles Times wrote in 1999. “She’s about to get a housekeeper of her own." But since Gary Winnick’s death at the age of 76 in 2023, a very different financial picture has come to light. For all his flashy possessions—a storied Bel-Air estate known as Casa Encantada, a Malibu beach house, a New York pied-à-terre and an enviable art collection—he was severely strapped for cash and deeply in debt.

His 79-year-old widow, Karen Winnick, is now fighting to keep control of their homes, art and jewelry, all of which Gary put up as collateral against a massive loan. The revelations have shocked L.A.’s upper crust, and even some of the couple’s closest friends, many of whom assumed that Gary had almost unlimited financial resources. “How this was not better managed is just totally beyond me," said Lori Hyland, whose late husband, L.A.