That you are surprised
he's made some fairly inane gaffes (for - as you pointed out- a pedigreed Ivy-leaguer) doesn't surprise me. The majority of the media has a vested interest in propping the man up and if a misstatement (and that's all these are) isn't uttered by a Republican, it holds little interest for the media. The media refused to do it's job leading up to the November 2008 election, but those of us who had an interest in learning of his background, his mentors, his actions, his lack of experience... well, suffice it to say we are not surprised that he governs using tactics straight out of Alinsky 101.
I respect the office, but he - Barack Obama - gets the same level of respect he gives to those who don't worship him or hang on his every word... even in your imaginary meeting scenario.
He is all "Chicago-Way" politics, enriching his friends and supporters as he stumbles along and he has failed at the job he was elected to do, which was to provide leadership... be the leader of all the American people... just my opinion.
Who knows... he may still maneuver his way out of the box he's built for himself, but he has a little over one year to do it.
Be thankful I didn't take you up on your bet... you would've lost.