Gary Winnick

Winnick was born on October 13, 1947, in New York City and grew up on Long Island in an entrepreneurial family: one grandfather sold restaurant supplies in the Bowery, the other had a garment factory, and his father, Arthur, ran a food service equipment business that later failed, though Winnick said it never occurred to him not to go into business. After high school, he attended college close to home at the C.W. Post campus of Long Island University, and before entering finance he worked in furniture sales.⁠[1][1][1][1]

In 1972, Winnick joined the Wall Street investment bank Burnham & Co.; after Michael Milken set up his junk bond operation in Beverly HillsBeverly HillsBeverly Hills is an incorporated city in Los Angeles County, California, known for its film-industry residents, Rodeo Drive shopping district and hotels. Incorporated on January 28, 1914, it covers about 5.71 square miles and recorded 32,701 residents in the 2020 census. It operates under a council–manager system. The Metro D Line extension reached Wilshire/La Cienega in May 2026.Open the full entry in 1978, he moved to the West Coast and learned the telecommunications business at the firm, later renamed Drexel Burnham Lambert, where he worked for 13 years in all. Drexel collapsed a few years later amid insider trading allegations, and Milken pleaded guilty and went to prison; Winnick was never accused of wrongdoing but had been subpoenaed to testify before the case was settled.⁠[1][1][1][1]

In 1985, Winnick left Drexel and founded the investment firm Pacific Asset Management. Before founding Global Crossing, the investment firm he ran was named Pacific Capital Group, which he confirmed at a 2002 congressional hearing still existed. He later recalled that he first retired at age 37 and “lasted through lunch.”⁠[1][2][1]

In 1997, Winnick founded Global Crossing. He told Congress that the company began as a single transatlantic undersea cable financed by him and his partners, something that had not been done privately in some 125 years, and that its early success led them to build a global telecommunications network. The company’s plan was to lay undersea fiber-optic cable to meet the rapidly growing bandwidth demand of internet companies in the late 1990s, and it ultimately laid more than 100,000 miles of cable; Winnick raised more than $20 billion for the project and served as the company’s nonexecutive chairman.⁠[2][2][2][1][1][3]

Global Crossing went public in 1998 and then acquired telecommunications companies including Frontier Corporation. In 1999 the company was worth more than $50 billion and Winnick’s stake about $6 billion, putting him at No. 1 on the Los Angeles Business Journal’s list of the wealthiest Angelenos.⁠[4][2][1][1]

In 2000, Winnick and his wife bought Casa Encantada, a historic mansion in Bel-Air, Los Angeles, from David H. MurdockDavid Murdock (Dole)David Murdock (1923–2025) was an American entrepreneur and investor who left school at 14, got his start building homes in Phoenix, and became known for acquiring controlling stakes in public companies. From 1985 he ran Dole and its parent company Castle & Cooke for decades, took Dole private twice, and for many years owned most of the land on the Hawaiian island of Lanai; late in life he invested in the North Carolina Research Campus, focused mainly on nutrition and longevity research.Open the full entry for $94 million, at the time a record price for a home in the United States. The 60-room Georgian mansion, completed in 1938 and overlooking the Bel-Air Country Club, had belonged to hotelier Conrad Hilton; Murdock had also set a record when he bought it for $12.4 million in 1980. Winnick then had designer Peter Marino lead a restoration costing tens of millions of dollars.⁠[1][5][5][5]

The internet bubble burst in 2000, and with it the projected bandwidth demand on which Global Crossing’s expansion depended. On May 23, 2001, Winnick sold nearly 10 million shares of Global Crossing stock for about $123.5 million; notes from a management meeting a week earlier showed the company’s revenue forecast for the quarter falling about $360 million short. Over the years, he sold more than $600 million worth of Global Crossing stock in total.⁠[1][1][2][2][2][1]

On January 28, 2002, Global Crossing signed a letter of intent with Hutchison Whampoa and Singapore Technologies Telemedia under which the two companies would invest $750 million for a joint majority stake in the restructured company, and at the same time filed for Chapter 11 in the U.S. Bankruptcy Court for the Southern District of New York, with coordinated proceedings in the Supreme Court of Bermuda. The company had $12.4 billion in debt, and it was at the time the fourth-largest bankruptcy on record in the United States; investors, including many employees who held stock through their 401(k) plans, were wiped out.⁠[6][6][6][4][1]

In August 2002, Global Crossing cancelled a public auction and accepted a $500 million bid from Hutchison Whampoa and Singapore Technologies Telemedia, under which the two companies would receive 61.5% of the reorganized company in return for $300 million in cash and about $200 million in notes, while existing shareholders received nothing.⁠[4][4][4]

On October 1, 2002, Winnick testified under oath as chairman of Global Crossing before the Oversight and Investigations Subcommittee of the House Energy and Commerce Committee, rather than invoking his Fifth Amendment right not to testify. In his opening statement, he said that, based on the facts known to him, the company’s bankruptcy was not the result of fraud but of a catastrophe that befell an entire industry. Regarding his May 2001 stock sale, he said the company had just reconfirmed its guidance on an analyst call, so the sale was not based on information that was not available to the public; as chairman, he said he was not aware of executives’ warnings about the company’s financial difficulties.⁠[2][2][2][2][1]

At the hearing, Winnick pledged that he and his family would personally contribute about $25 million, writing a check to the administrator of the company’s 401(k) plan to make up employees’ retirement losses, and called on chairmen and chief executives of other companies to do the same. Subcommittee Chairman James C. Greenwood said the pledge had shocked a lot of people; he also noted that it was not only employees who had lost $25 million, but investors who lost about $54 billion in the company’s collapse. The pledge was welcomed by some employees but criticized by others as stingy.⁠[2][7][2][2][2][1]

On March 19, 2004, Winnick and other former Global Crossing officers agreed to pay a combined $325 million to settle a securities fraud class action led by the Public Employees Retirement System of Ohio and the State Teachers Retirement System of Ohio; Winnick personally contributed $55 million, the company’s law firm Simpson Thacher & Bartlett contributed $19.5 million, and insurers paid the rest.⁠[8][8][8][8][9][9]

On July 20, 2004, the U.S. Department of Labor announced a $79 million settlement with former Global Crossing officers and directors over the employee retirement savings plan, under which Winnick paid $25 million from an irrevocable escrow account, fulfilling the pledge he had made to Congress, while the remaining $54 million came from insurance. The settlement barred Winnick and the others involved from acting as fiduciaries of benefit plans covered by the Employee Retirement Income Security Act (ERISA).⁠[10][10][10][10][10]

In December 2004, the U.S. Securities and Exchange Commission decided not to bring civil charges against Winnick or impose the $1 million fine that had been expected. The SEC’s two-year investigation found no evidence of fraud or insider trading, but found that company executives had failed to provide adequate disclosure about certain critical swap transactions. The SEC’s enforcement staff had recommended charges, arguing that although Winnick held the title of nonexecutive chairman he functioned as a hands-on officer who came to the office every day and was involved in major decisions; Chairman William Donaldson, however, believed he was not sufficiently involved in day-to-day operations, and together with two other Republican commissioners overturned the recommendation, over the objections of the two Democratic commissioners.⁠[11][3][11][3][3][3][3][11][11]

The Department of Justice likewise decided not to charge Winnick. He long maintained that he had done nothing wrong and was the victim of a market collapse.⁠[1][1]

After the fall of Global Crossing, Winnick kept a low profile, focusing mainly on family philanthropy and investing through his family office investment firm Winnick & Co. In a 2015 interview with the Los Angeles Business Journal discussing plans to invest in Los Angeles tech startups, he said, “I have no apologies for anything,” and called Global Crossing transformational, saying the internet would not be the internet today without that network.⁠[1][1][1][1]

In October 2019, Winnick listed Casa Encantada for $225 million, then the highest asking price in the country, but no buyer was found. In June 2023, Winnick and his wife listed it again for $250 million; Winnick called the house a work of art and said he had been its steward.⁠[12][12][13][5][5][5]

In November 2023, Winnick died unexpectedly at his Bel-Air home at the age of 76 and was buried at Mount Sinai Memorial Park in Los Angeles. He had been married to his wife, Karen, for 51 years.⁠[1][1][1][1]

Winnick died more than $150 million in debt. During his lifetime he had obtained a loan from CIM Group secured by assets including Casa Encantada and a Malibu home; after his death the loan went into default and CIM began foreclosure on Casa Encantada. In 2025, his widow, Karen Winnick, filed a cross-complaint in Los Angeles Superior Court accusing CIM of a “loan-to-own scheme” that turned an initial $100 million loan into $155 million in debt, and said she had not understood the terms; CIM denied any wrongdoing. The Winnick family’s attempts to stop the foreclosure were rejected in turn by the trial court, the Court of Appeal and the California Supreme Court.⁠[14][14][15][16][16][15]

Meanwhile, the asking price for Casa Encantada was repeatedly cut, standing at $195 million in October 2024; in April 2026, the Winnick family relisted it for $170 million. In July 2026, at a foreclosure auction held in Pomona, the house was bought by Peter ThielPeter ThielPeter Thiel is an American entrepreneur and investor, a co-founder of PayPal and Palantir Technologies, and the first outside investor in Facebook. He is a partner at the venture capital firm Founders Fund and founded the Thiel Fellowship, which funds young people to leave college and build new things; his public skepticism of higher education, his support for Trump in 2016, and his funding of litigation against Gawker Media have drawn controversy.Open the full entry through a limited liability company for $130 million.⁠[13][17][17][17]

During Global Crossing’s heyday, Winnick contributed more than $100 million to organizations including the Special Olympics, the Los Angeles Zoo and the Simon Wiesenthal Center, becoming one of Los Angeles’s leading philanthropists. He also served on the board of the Museum of Modern Art in New York and hosted fundraisers and cultural events at Casa Encantada.⁠[1][14]