The American Dream is often sold as a linear climb, but for Gary Winnick, it was a vertical ascent followed by a devastating, high-speed freefall. Once the wealthiest man in Los Angeles with a net worth of $6.2 billion, Winnick’s legacy reached a somber milestone this week. As of December 2025, the crown jewel of his empire—the storied Casa Encantada mansion in Bel Air—is facing a foreclosure auction to satisfy debts exceeding $150 million.
It is a “billions to bust” story that rivals the most dramatic Wall Street scripts, beginning in the junk-bond trenches of the 1980s and ending with a widow fighting to save a home that was once the most expensive ever sold in the United States.
The Junk Bond Architect
Gary Winnick didn’t start at the top. A native of Long Island, his early career was defined by the high-octane environment of Drexel Burnham Lambert. Working at the infamous X-shaped trading desk in Beverly Hills, Winnick was a key lieutenant to Michael Milken. Together, they pioneered the use of high-yield “junk bonds” to fuel corporate takeovers, fundamentally reshaping the landscape of American finance.
Winnick mastered the art of leveraged finance, but he wanted more than to be a trader—he wanted to be a titan. In 1997, he founded Global Crossing, a telecommunications company with a goal as audacious as its founder: to lay a global fiber-optic network under the world’s oceans to meet the exploding demand for internet bandwidth.
It is a “billions to bust” story that rivals the most dramatic Wall Street scripts, beginning in the junk-bond trenches of the 1980s and ending with a widow fighting to save a home that was once the most expensive ever sold in the United States.
The Junk Bond Architect
Gary Winnick didn’t start at the top. A native of Long Island, his early career was defined by the high-octane environment of Drexel Burnham Lambert. Working at the infamous X-shaped trading desk in Beverly Hills, Winnick was a key lieutenant to Michael Milken. Together, they pioneered the use of high-yield “junk bonds” to fuel corporate takeovers, fundamentally reshaping the landscape of American finance.
The $50 Billion Colossus
For a brief window in the late 1990s, Winnick’s vision seemed infallible. Global Crossing’s market value soared to $50 billion. On paper, Winnick was worth $6.2 billion, making him the richest man in Los Angeles. His wealth was so vast and his spending so flamboyant that he became the poster child for the “New Economy” excess.
At the peak of his power in 2000, Winnick and his wife, Karen, purchased Casa Encantada for $94 million. At the time, it was the highest price ever paid for a home in U.S. history. The 40,000-square-foot Georgian-style estate, which sits on 8.4 acres overlooking the Bel-Air Country Club, was more than a home; it was a museum. The Winnicks spent tens of millions more on renovations, hiring hundreds of artisans to restore the property to its 1930s glory, including a dining room with Japanese-inspired lacquer finishes.
At the peak of his power in 2000, Winnick and his wife, Karen, purchased Casa Encantada for $94 million. At the time, it was the highest price ever paid for a home in U.S. history. The 40,000-square-foot Georgian-style estate, which sits on 8.4 acres overlooking the Bel-Air Country Club, was more than a home; it was a museum. The Winnicks spent tens of millions more on renovations, hiring hundreds of artisans to restore the property to its 1930s glory, including a dining room with Japanese-inspired lacquer finishes.
The Bubble Bursts
While Winnick was hosting fundraisers and cultural events for the elite at Casa Encantada, the foundations of Global Crossing were eroding. The company had borrowed $12 billion to build its network, betting on a “bandwidth boom” that arrived far slower than predicted.
In March 2000, the dot-com bubble burst. Startups that were Global Crossing’s primary clients evaporated, and revenues plummeted. In January 2002, Global Crossing filed for Chapter 11 bankruptcy. It was the fourth-largest bankruptcy in U.S. history at the time, wiping out tens of billions in shareholder value and the pensions of thousands of employees.