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Chief Executive Officer, Global Crossing
Perhaps the most ruthless of them all, the man Fortune calls 'The Emperor of Greed'. While his former employees in Rochester struggle desperately to make ends meet, Winnick is renovating his 'palace' in California, the most expensive single family residence in the US, worth close to $100 million. With the help of his long-time friends on the street, Winnick was able to keep his company's stock afloat long enough to gut what was left - a net for Winnick of $734 million.
But Winnick's initial investment in his company, $15 million, was only worth $8 million when the company collapsed, so the question of who that $734 million really belongs to is a valid one.
Winnick is the disciple of Michael Milken, the guru of the junk bond scandal of the 1980's. While Milken went off to be the guest of the government for dubious practices at Drexel Lambert, the disciple went on to found Global Crossing.
It is unlikely the US federal government will come down as hard on Winnick as it did on Ken Lay, for the simple reason that Winnick hedged his bets better. While Lay just threw political money around indiscriminately (but mostly to Republicans), Winnick targeted his money carefully and made sure all his accomplices were thoroughly compromised. Former president George HW Bush got a cool $14 million off a very shady deal with Winnick; the chairman of the Democratic National Party did the same.