Company: eBay (1998 - 2007)
Biggest asshole moment: Shoving an employee in an executive conference room, which resulted in a financial settlement of around $200,000.
Outsiders admired her for transforming eBay into a billion-dollar business, but employees reportedly perceived her as a rageaholic who could not complete a sentence without swearing and attacked employees. One alleged altercation in 1999 had her throwing a phone at a marketing exec because the eBay site crashed, while another, in 2006, had her spazzing on recruiters for not interviewing a candidate: "Are you fucking kidding me with this shit? Do I have to fucking do everything myself?...I don’t need this fucking shit.” However, nothing topped her 2007 shoving incident with employee Young Mi Kim right before a scheduled media interview. Kim threatened to sue the company and walked away with a six-figure settlement. Whitman resigned as CEO in 2007 and eBay employees have sighed in relief ever since.