Moreover, I think he tries too much to make these high level interviews about himself, by pretty much saying "I know more than you do and I can dominate whichever league you're playing".

With Olbermann, it'll be a lovefest because he thinks he's making up for the terrible abuse Obama may have suffered at the hands of O'Reilly.

And even with the softballs, Obama is coming across a bit awkwardly. He's had a couple of good lines --"Republicans are pretty good at working the refs" -- and he just paid tribute to the economy under Bill Clinton, but I think he needs to work up a little more outrage about the economy, and the Republicans' failure to address it.

"Republicans aren't change" or "we're going to move in a fundamentally different direction" isn't good enough. He is not tying Bush's economic failures to McCain. For all some people know, when Obama says McCain is no change, he might be talking just about Iraq.

Obama needs to pin the tail on the elephant. "McCain is going to continue the same economic policies that got us into this mess" or "Are you going to rehire the folks who got us in this mess, or are you going to fire them?"

And Obama should need to fed these lines by KO, anyway.

I thought Obama looked weak when he at first refused to acknowledge OReilly's points.  My impression was that Obama was in command of the facts but was trying to not acknowledge that some would lose under his plan.  He recovered at the end of the interview when he finally admitted that some would pay more and couched it in human terms of a minimum wage waitress struggling to get by vs OReilly and himself paying a bit more.

The fact is Obama is in favor of income distribution.   That's a legitimate position. Many agree with him.  He should figure out how to say so in a politically palatable way.  Waffle waffle waffle makes him look weak.  There are clear differences between the candidates on the issues.  Not everyone is going to always agree with you. I think it is a mistake to try and not offend anyone.  It makes you look weak.

OReilly made the point at the start of the interview that he had to cut Obama off / keep him on track because he was only given 30 minutes for the entire interview.  He knows it makes him look aggressive (rude?) and acknowledged he had complaints about that style. To be fair, Obama's speaking style has been described many ways but rarely described as concise and to the point.  It's probably OReilly's only shot at Obama.    Obama wanted to be during the RNC.  Both sides made tradeoffs.

I actually like O'Reilly's style of not letting Obama get away with rambling or get into his talking points.  I'd like it better if a similar style was applied to both (or all 4 candidates).  It is rare to see a candidate get thrown off their pre-scripted answers and not be able to hide.  When it happens, it shows the depth (or lack thereof) of the candidate's knowledge.   No matter what you think of Obama, it would be hard for anyone to make the case that he doesn't understand a great deal.  He looks on top of his facts.

Later on in the show, OReilly called Obama a very tough guy, a very determined driven man.  He said he could only learn that face to face.  He aid he was very impressed.