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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
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).

The Cosby ShowWMG/Live Action TVCovert Affairs

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