Keith Olbermann MSNBC "History Will Repeat Itself!"

As an employee, Olbermann was his own kind of Worst Person in the World. His sense of superiority and caustic vibe eventually cost him gigs and friends at three networks. How naughty was he? Olbermann was the only former ESPN star not invited back for the sports network’s 25th anniversary (he’s allowed to participate on Patrick’s radio show only because Patrick promised that Olbermann would never set foot on the network’s Bristol, Connecticut, campus). He was fired from his first stint at MSNBC after he denounced his own show in a commencement address at his alma mater. Fox hired him to host its major-league baseball Game of the Week and then sent him home with a year left on his contract simply for being a malcontent.