8. Global Crossing Ltd; $30.19 billion
Founded by Gary Winnick and three business associates in 1997 through Pacific Capital Group, Winnick's personal venture group, Global Crossing Limited is a telecommunications company that provides computer networking services worldwide.
The company is legally domiciled in Bermuda, although its administrative headquarters are in New Jersey. Global Crossing's rapid rise and fall attracted tremendous attention and it was quickly revealed that the company, particularly its executives, lavishly spent money on "themselves and their digs."
Four of Global Crossing's CEOs received at least $23 million in personal loans from the company, some of which were forgiven entirely even when bankruptcy was becoming a greater possibility. These same CEOs also received over $13.5 million in after-tax signing bonuses along with lucrative stock options. Between 1998 and 2001, Winnick sold approximately $420 million in Global Crossing stock.
Even as the company's financial situation went from questionable to grim, work continued on Winnick's Bel Air mansion, valued at $92 million and considered the most expensive home purchased in Los Angeles.
The company, inevitably, filed for bankruptcy on January 28, 2002.
In 2004, Global Crossing settled a class action lawsuit over the losses the employees incurred from their pensions and 401Ks. Investors and former employees received $325 million in settlement. Winnick contributed $30 million to the settlement.
Since emerging from bankruptcy, the company has attempted to re-focus its business.
Image: Chairman of the Board of Directors Gary Winnick of Global Crossing Ltd reacts as he testifies during a hearing before a House subcommittee on oversight and investigations on Capitol Hill | Photograph: Alex Wong/Getty Images
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