He appears he was a primadonna from way, way back:
Olbermann’s tenure at ESPN was characteristically contentious. One of his co-anchors, Suzy Kolber, has said that Olbermann was sometimes so overbearing that she would lock herself in the bathroom and cry. Another colleague, Mike Soltys, has said that when Olbermann left the network, in 1997, “he didn’t burn bridges here—he napalmed them.”
However, if it weren't for Bill O'Reilly, Olbermann wouldn't be where he is today. Olbermann created a "feud" between the two, and he's ridden to fame on this every since. It helped open the door for Olbermann to be the second coming of Eric Severeid and provided viewers something that would already reinforce their beliefs.
Olbermann's political slant towards Obama became increasingly evident as the campaign season wore on:
Olbermann says that he began the campaign season determined to remain neutral on the Democratic race, although he was plainly friendly with the Clintons. (During an interview with Bill Clinton in 2006, Olbermann handed the former President a personal donation to the Clinton Foundation.) Olbermann liked Obama, but he believed, at first, that he would not make a strong candidate. As the tide began to turn Obama’s way, Olbermann began to grow impatient with Clinton surrogates’ attacks on Obama, and, seemingly, with the persistence of the candidate herself. As Obama neared apparent assurance of the nomination, Olbermann began to raise questions about Clinton’s arithmetic on the popular vote, about her wanting to change the rules regarding the Florida and Michigan primaries, about why she didn’t just do the right thing and get out.
He turned into a total hack, a total jerk. Olbermann risked turning off a huge chunk of his audience with his sleazy, sexist attacks on Hillary Clinton:
But, just as Obama must work to win Clinton supporters for the fall campaign, Phil Griffin has to repair a fractured audience base, a portion of which saw sexism in his network’s Clinton coverage and vowed to boycott MSNBC. Griffin knows that some of that anger is aimed at his star anchor. “It was, like, you meet a guy and you fall in love with him, and he’s funny and he’s clever and he’s witty, and he’s all these great things,” Griffin said of the relationship between Olbermann and the Clinton supporters among his viewers. “And then you commit yourself to him, and he turns out to be a jerk and difficult and brutal. And that is how the Hillary viewers see him. It’s true. But I do think they’re going to come back. There’s nowhere else to go.”
I think the damage is irreparable.
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