You're a damned fine writer, and you have a good sense of humor—both evidenced in this OP.
However, I think your assignment of blame for Keith's “going over to the dark side” ( a common epithet hurled at him these days by certain disappointed folks) to his association with and influence from his guests misses what really went down with him.
He was pretty down-the-middle with Obama and Clinton until Senator Clinton pushed a big, red button on him that seems wired directly into the pain centers of his central nervous system.
That “big, red button” was the “fear” card. When Sen. Clinton started playing some of the terror/fear verbal games (albeit without the same bared teeth zeal) as the hated Rudy Giuliani, it set Olbermann off. Now that may not be fair, but it IS a known raw nerve for him. He's made MSNBC a resurgent force in cable news in large part due to his indignation over Bush, Cheney and their flunkies on the right side of the aisle's playing that card so often that it's paper-cut their fingers down to the bone. The “fear” card is Keith's
http://www.youtube.com/watch?v=-WIQ67vRg6c&feature=related">“Susquehanna Hat Company” trigger (an old vaudeville routine where a seemingly mild-mannered fella goes ballistic at the mention of the hat company). I personally don't have a problem with that being a lever that flips him—it's a legitimate issue that should set most people off. It certainly did with Giuliani, as it even turned New Yorkers—the people most directly affected by 9-11 against him, and that's saying something, considering how Rudy was lionized for his “handling” of things on that fateful day.
“America's Mayor” wound up a pariah in his own city for his naked over-pandering. It set people against him in a bad way. People who were celebrating him mere months before.
I remember Olbermann's almost trembling with rage when Sen. Clinton went there. His whole vibe was “how could you?”, and he hasn't gotten over it. It seemed to be a deal-breaker for him and he's been at best, skeptical of her and her candidacy ever since. I believe it was January of this year when it went down—just before New Hampshire's primary.
http://www.youtube.com/watch?v=7BB4Vvgn_4k">Here's a YouTube link from around the time it all blew up. People at the time remarked on how upset and angry he seemed over this. I noticed it too. It wasn't guests turning him with crafty power-of-suggestion verbal undernotes. The “fear card” moment was a corner he turned with her and he hasn't looked back since.
And while I can semi-understand her “going there” to blunt the GOP's domination of that spur of the discussion, going “there” is the one thing that everybody knows gets Olbermann fired up like few other bits of political gamesmanship. He'd spent the last two years roasting Cheney and Bush every time they pulled that and it seemed to genuinely shake him when the senator from NY supped at that table too.
You could hear the camel's back snap like a dry twig that week.
Wolffe? Buchanan? Good as they are, they ain't Svengalis. She (Sen. Clinton) pushed the wrong button on the wrong pundit/journalist and she's paid for it ever since.