Keith has never thought of it as self sabotage - what he actually thinks of it as is pre-emptive self protective instincts. After all if he's going to fuck up in a spectacular fashion then he figures he may as well do so on his own terms rather than another persons timetable.
(Dan is the exception but then Dan has always been a mysterious exception to everything in Keith's life - he's beginning to think that it's just that Dan has some kind of magical power. Or they got out of working together before Keith had gotten really bad. It's probably a little of both).
So Keith has arrived at his current (perfected) state of curmudgeonly stubborn bridge nuking but he's also arrived with a possessive streak that has followed him all his life, despite his best efforts to shake it because it's entirely and completely unreasonable and he knows it but it's always always been a part of him, even as he is burning bridges. He also manages to be jealous of any hold anyone has on any of his friends...while refusing to have anything to do with the friend in question himself.
Keith Olbermann has never said he was sensible in any sense.
He hates that Rachel has her own show, because it means she belongs to a whole other set of people once again. Even though he had as much to do with promoting the idea that she should be on TV regularly as probably anyone he still resents the fact that she has a separate show. A separate set of people who have claims on her, her time, her brain and her laughter. And it's not him alone. He knows that it was never him alone. There was Susan and that ridiculous bloody dog and her family but he can still feel the envy eat away at him that they have so much of her and he does not.
Susan is a wonderful woman - sweet, brilliant and incredibly funny and she and Rachel adore each other and Keith? Keith hates her, bitterly and hates himself for it because he likes Susan very much really but he can't shut out the voice that says 'that's my Rachel, it isn't your Rachel'
This is why he's so incredibly, mind bogglingly fucking unqualified to engage in relationships in general, Keith had said once to Dan, who'd just made a snorting noise in his general direction and called him some kind of ridiculous name.
Keith Olbermann has lists of his jealousies.
He is jealous of Richard Wolffe going on other peoples shows and on the campaign trail in general. He's jealous that Gene Robinson made friends with Rachel and Rachel made friends with Gene. He is jealous of Melissa and Rachel and their easy, happy friendship. He is jealous of Jon, Stephen, Rachel and Richard. And Richard. Richard bloody Engel. Richard Engel the foreign correspondent, blithely and charmingly going into danger. Richard Engel, the effortlessly unaware of his good looks. Richard Engel who can speak fluent Arabic and knows as much about getting around war zones as Anderson.
He and Anderson aren't friends, not exactly. They are not enemies or strangers but they are not friends. They certainly have friends in common (Jon, Stephen and Rachel), they have regular social events in each others company and they even have fun bantering but they are not friends. They have, Keith thinks, an uneasy relationship. Keith needles Anderson about anything and everything (mostly about how Anderson has a terrible show, terrible media choices and terrible choices in regards to the disclosure of his personal life) but he'd be the first to turn on someone else who attacked him. Anderson makes him incredibly angry and incredibly admiring all at once and it's distinctly uncomfortable for Keith to articulate exactly why this and therefore exactly what Anderson is to him.
And yet, he is still jealous of those who count Anderson as friends. It's a kind of white hot jealousy that makes him want to needle Anderson more than ever.
When he sees Anderson, Richard Engel and Rachel together he feels sick and spends all his time making barbed remarks about 'infotainment airhead journalism' the next time he sees Anderson at lunch. Variously Rachel, Jon and Stephen have tried to intervene and talk to him about it but Keith dodges them. He does not want to talk about anything relating to Anderson Cooper. Not now, not ever. Especially not now, watching Engel, Rachel and Anderson with their easy chemistry and their arms around each others shoulders. The way they have in jokes and travel stories and similar interests and and a something that he will never share.
When Keith Olbermann leaves MSNBC he makes sure to blow up all the bridges behind him as thoroughly as he can. It's easy enough to make it clear enough he never wants to talk to any of them, ever again. It's easy enough to change his number, change his habits and change his eating spots. It's easy enough to be insulting and ignore the times that Dan tries to talk to him about his life choices. Much better this way. Much cleaner, much less chance of leaving any kind of scar. In any case, he's happy where he is and Cooper is an annoying rich boy, aping Batman.
Keith doesn't keep up with his former friends. Dan does. Dan will inform him of certain things. Things like Rachel and Susan adopting a second dog, Rachel becoming an honorary aunt to Melissa's baby and to her new friend Chris' kids, Richard Wolffe going to work for the Obama administration, Richard Engel's capture and rescue. Dan doesn't mention Cooper though. For Cooper? Keith finds himself trawling the gossip blogs.
When Anderson Cooper comes out? Keith nearly throws his iPhone across the room. When Anderson Cooper gets married, Keith Olbermann doesn't comment at all. When Anderson Cooper adopts a baby girl? Keith Olbermann makes no comment and refuses to believe he cares in any way. He even refuses to believe in his own jealousy. After all, he and Anderson were never even friends. Not really.
He never expected to actually like Keith. Anderson still remembers the times he was fairly sure he just downright could not stand being in a room with Keith and yet, he liked him.
Which is a very strange place to be in.
They were friends of each other's friends (Jon and Stephen and then Rachel and various) but Anderson? Anderson was fairly certain they'd never have gotten on at all, alone and yet some of the best discussions he's had in his life? He had with Keith. Not about journalism, which is a subject that genuinely does divide them with rancour but other things - sport (all kinds, though Anderson cannot understand Keith's loathing for soccer), politics (sometimes), the art of writing (Anderson edits Keith's sentences and Keith adds that touch of soaring oratory to Anderson's), nature and one memorable night, American Idol (somewhere there lives a photo of Keith with a tiara upon his head, blithely bellowing a song).
Anderson still wouldn't call them friends. It's not even that he has a crush on Keith (back then) - he's had that with friends before - it's that there's a streak of genuine cruelty in some of Keith's barbs - something that wants to just hurt and it crashes up against something in Anderson that wants to hurt back just as viciously and just as cruelly. They do not bring out the best in each other, in the end.
(Maybe, Anderson thinks later, if things had been a little different they might have been wonderful together. But things are not a little different - they are what they are).
Anderson knows that. He regrets the way Keith severs so many of his connections to people and that all Keith can do is (it seems) destroy relationships pre-pre-emptively and he regrets the loss of their not a friendship but still comforting companionship but he does not regret having met Keith Olbermann.
(Even if Keith seems to regret having met him. Among many other people - Keith seems to go through life regretting meeting people he'd called friends and companions).