Carly Fiorina

Company: HP (1999 - 2005)

Biggest asshole moment: Forced soon-to-be fired employees to train their outsourced replacements.

Judging by a resume that consisted of 30,000 firings and a 50-percent HP stock decline, Fiorina is a sure shot for any worst CEO list. In 2001, she suggested employees take voluntary pay cuts, and while 86 percent agreed, she still outsourced thousands of jobs overseas and implemented huge layoffs. A 2008 article in Entrepreneur Magazine touched on the employee morale during Fiorina’s reign: "A survey of 8,000 employees revealed widespread unhappiness about poor communication and poorly implemented decisions...Some workers booed the CEO at company meetings.” Even during her run for Senate last year, Sen. Barbara Boxer released a viral ad claiming Fiorina fired thousands and “tripled her salary, bought a million dollar yacht and five corporate jets” as CEO. HP cut her loose and offered a $42 million severance package to never come back. After hearing the news, employees rejoiced and supposedly proclaimed, “The witch is dead.”