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16. Gerald Levin

Levin’s failure comes down to one colossal mistake: In his desperate eagerness to become a new-media CEO, he orchestrated a megamerger between Time Warner and a vastly overvalued AOL—one of the worst acquisition deals ever. “He had the largest midlife crisis in the history of American capitalism,” one of our panelists quipped.

THE STAT: The AOL deal destroyed over $200 billion in Time Warner shareholder value.

Time Warner Company Website

By Portfolio.com