From $6B to bust: How Gary Winnick, LA’s richest man, lost it all after owning one of US’s priciest mansions
[Special thanks to David S. Luber (Florida Probate Attorney) for bringing this article to my attention.]
The former junk bond trader who was once the richest man in Los Angeles, with a net worth that peaked at $6.2 billion, saw his fortune collapse, leaving behind a widow now fighting foreclosure on one of America’s most storied mansions.
Gary Winnick, a Long Island native and former Drexel Burnham Lambert executive, rose in the 1970s and 1980s working alongside Michael Milken, mastering leveraged finance at the height of Wall Street excess.
His wealth surged during the late 1990s internet boom. At his peak, Winnick was widely considered the wealthiest man in Los Angeles and was said to be so rich that even his housekeeper became a millionaire. By the time he died in 2023 at age 76, however, he was more than $150 million in debt.
Winnick built Global Crossing into a telecommunications giant valued at roughly $50 billion, borrowing heavily to construct a global fiber-optic network based on projections of exploding demand for bandwidth.
He spent accordingly. In 2000, Winnick and his wife, Karen, purchased Casa Encantada, the famed Bel Air estate once owned by Conrad Hilton and David Murdock, for $94 million, then the most expensive home sale in U.S. history. Tens of millions more were spent restoring the 40,000-square-foot estate to museum-level standards.
The couple amassed a portfolio that included a Malibu beach house, a New York pied-à-terre at the Sherry-Netherland Hotel, and a significant art collection featuring artists such as Cy Twombly and Edward Hopper. Winnick also served on the board of the Museum of Modern Art and hosted high-profile cultural events.
The collapse began in March 2000, when the dot-com bubble burst and Global Crossing’s startup clients ran out of cash. Revenues plunged while debt ballooned into the billions.
In January 2002, Global Crossing filed for Chapter 11 bankruptcy, erasing tens of billions in market value and costing thousands of employees their jobs. Pension funds and shareholders sued, alleging executives had misled investors.
Winnick had already cashed out roughly $730 million in stock before the collapse. In 2004, he paid $55 million to settle shareholder lawsuits and was never criminally charged.
Despite the fallout, Winnick continued funding an extravagant lifestyle and investing in media and technology ventures, many of which later failed or ended in litigation. Legal battles multiplied, driving up borrowing costs.
By 2023, his debt had grown to approximately $155 million. That year, Casa Encantada was listed for $250 million, the highest asking price in the country at the time, but the sale never closed.
After Winnick’s sudden death on November 3, 2023, two weeks before a scheduled deposition, his widow said she learned for the first time that their homes, art, and even her wedding ring had been pledged as collateral. Following default, CIM, the lender behind a $100 million revolving loan secured by personal assets, moved to foreclose on Casa Encantada and the Malibu property.
The estate that once symbolized Gary Winnick’s rise ultimately became the centerpiece of his downfall.
For more information see Ariel Zilber “From $6B to bust: How Gary Winnick, LA’s richest man, lost it all after owning one of US’s priciest mansions,” New York Post, December 19, 2025.