Larry Ellison (Oracle)
Douchiest moment: Admitted to dating three Oracle employees…at the same time!
Look up the term billionaire playboy and chances are you’ll see Larry Ellison pictured. The ridiculously wealthy CEO who owns his own island put his charm to the test by messing around with three of his employees, at the same time. A female ex-employee, with whom Ellison had an affair with, launched a lawsuit alleging he tempted several female employees into bed with the offer of an Acura sports car. Ellison claimed it was a joke, but admitted when questioned that he had bought four Acuras in the previous year.
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