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I just watched a lot of Keith Olbermann on youtube (my head is spinning.) Now I can present an 'educated opinion' 
First: tcaud et al, if he is ESTj, I would have to seriously reconsider my benchmarks for that type... He seems to use quite a bit of Ne--more than others ESTjs I've seen... For example, compare Olbermann's frequent use of Ne (and lack of Fi) to an ESTj in a comparable position, CNN HN personality Nancy Grace.
That said, tcaud, what you write about Olbermann's comment to Obama DOES seem to me to be an expression of Te, (like you interpreted it.) However, it does not seem to be out-of-line with 8th function Te, i.e. 'using Te to sell ideas,' (put very simply.) He was, after all, using it to persuade Obama (who may or may not have been watching--or had an aid watching.) In the videos I watched, I did see Olbermann use a lot of Te.
I considered INTp as well, b/c it was mentioned in this thread... Like I said, Olbermann DOES use a lot of Te; however, he does not use it incessantly, e.g. Ben Stein (INTp) or Gore Vidal (INTp,) who do... Whereas the Ni is blatant in Vidal and Stein, (just look at their faces, lol,) it is not with Olbermann... In fact, it's not a trait I noticed at all.
In thinking of ppl similar to Olbermann, (in terms of personality/presentation/sense of humor,) I thought of:
* Kevin Nealon
* Jon Stewart
* Larry David
Each of the above mentioned, I consider to be ENTp... Like them, I consider Olbermann to be ENTp... Probably the Ti subtype.
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