WMG / Countdown with Keith Olbermann

Keith timed his exit as both a Take That! to the network brass and a boost to his now-former colleagues.
He could've left a few months earlier, before the Lean Forward campaign; he could've left a week or so later, after the State of the Union. But he left after marketing spent a lot of money on new ads featuring him and the Friday before the biggest non-election event on the American political calendar, making a big splash and ensuring that many extra eyeballs would be on MSNBC. (Maybe not the Fox News crowd, but plenty of people who would normally have watched on CNN, C-SPAN, or one of the broadcast networks).

Keith was pushed out because MSNBC is owned by a big corporation that is willing to program liberal hosts as a market niche, but not economic populists (as that's bad for big corporations).
Keith's being pushed out isn't guessing: It's fact. Some MSNBC apologists might see it as due to Keith's abrasiveness...but normally you put up with an abrasive employee to get ratings. When you look at MSNBC's record, though, it likes its hosts to be liberals that focus on social issues (e.g. environmentalism, civil liberties/rights) or foreign policy (Rachel Maddow in particular is foremost anti-war).

Keith focused too much for MSNBC's brass on economic populism, including a stinging rebuke to President Obama when Obama extended all of Bush's tax cuts despite having a Democratic Congress at the time. Maddow agreed, but didn't focus on it. Lawrence O'Donnell actually supported Obama's decision.

Also angered by Obama's relative fiscal conservatism was Cenk Uygur, who was sent packing despite getting much higher ratings in the 6 p.m. slot than Ed Schultz had, and Schultz had been promoted to prime time. They offered Uygur more money if he would quietly move to an obscure weekend slot. He refused.

But then Schultz started getting aggressively into economic populism over proposed Social Security and Medicare cuts. He accepted getting moved to weekends, toned down his populism on those issues, and finally was let out of the penalty box back onto weekdays (though in a lesser slot).

MSNBC hosts like Chris Hayes and Maddow can be to the left of Obama, but Hayes focuses on social issues (especially environmentalism) and Maddow on war and peace. Focus on economic populism and MSNBC won't let you keep doing it.

  • As of now (late 2015) MSNBC has gotten rid of Schultz altogether as Schultz was, among other things, strongly behind Bernie Sanders' White House run (which is very anti-corporate), and is in fact rebranding the network away from liberalism. Maddow is the only liberal considered truly safe.

Keith was fired by ESPN due to his attitude vis-a-vis Roger Goodell
Look at the rest of the network: Will you find any serious criticism of the "business model" of the NFL? He has called the threat of franchise relocation "Shaking the taxpayer until their purses and their fillings fall out". He has frequently called on Goodell to resign and listed him in his "worst persons in the sports world". Now who does ESPN "happen to" have important contracts with? That's right.

And as for other issues (I have not a doubt in the world they exist), Olbermann has notably toned down his more over the top rhetoric from MSNBC days. He has been described as (for him at least) remarkably nice to colleagues. His departure was overwhelmingly described as friendly and professional (as opposed to previous firings that ended not only in burned bridges, but sometimes lawsuits). So maybe he was too expensive, but what kind of bad negotiator says "Hey I could get paid (less) doing what I love or I could ask for an unrealistic sum and get fired". Though it is of course always possible that the negotiations about money were all one giant misunderstanding or he somehow suspected MSNBC wants him back.

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