This whole Chicago Olympic bid was, from the start, a bit of happenstance that was going to make President Obama political trouble no matter how it ended. Unlike the movie theater, there was no happy ending to be had for Obama himself.
Let's consider the best case scenario: Chicago wins the bid after Obama jets in and is part of a whirlwind presentation to the IOC (International Olympic Committee) and is on his way back to D.C. before the voting is finished. That simply feeds into the narrative that has been woven by his opponents since he became the presumptive Democratic nominee: a smiling, charismatic politician fronting for crooked Chicago cronies in a political marriage of convenience. If Obama succeeded today, the story from conservative bloggers and news outlets would have been "Surprise, surprise... Obama came through yet again for his Chicago buddies in one of the biggest financial boondoggles of all: many millions of dollars flowing into the pockets of construction contractors to make the necessary improvements to host the game and then millions more in tourist dollars lining the pockets of the friends of Obama. It's good to be the king, er, emperor, er, The One." Remember, that was in the best case scenario.
A second scenario is that Obama doesn't go but Chicago wins the bid anyway. Not only does Obama's adoptive hometown feel pretty angry that the President was in a position to help it after all it had done to help him go from an Illinois state senator to the chief executive of the most powerful country in the world, but the opposition's refrain is now "Obama didn't go because he doesn't care about America and doesn't care if something important like the Olympics are hosted here... we said he was un-American and he has proven it yet again. The Democrats say that he is great for international relations and then he abandons his supposed 'hometown' when so much is on the line? He's not only un-American, he's ungrateful too." This is the second best outcome, which is pretty grisly.
A third scenario is that he doesn't go to make his pitch for the Chicago bid and the bid loses the vote. At that point, his hometown is extremely irate after losing while watching Obama do absolutely nothing and his opponents are saying "Obama is an ungrateful and un-American joke as President of this great country that cannot be bothered to do what all three other competing countries' leaders did: show up and make his argument why his country should be chosen to host the games. Who does this guy think he is anyway? This is contemptuous." However, this isn't yet the worst outcome.
The fourth scenario is what has just happened: Obama has put his reputation as a charismatic, lights-out closer on the line to bring the bid home for Chicago and the IOC thumbed its nose at Obama by voting Chicago's bid out in the very first round. Chicago is disturbed at losing but appreciative of their favorite son doing his best to try to carry the ball across the goal line for them. Obama, however, has handed his opponents a political gold mine as he climbed out on a limb too far and his opponents are now cackling and sawing it right out from under him. There is no need for me to suss out what his opponents would be saying because they are already saying it. Eric Erickson at redstate.com types “Hahahahaha. I thought the world would love us more now that Bush was gone. I thought if we whored ourselves out to our enemies, great things would happen. Apparently not,” while Rush Limbaugh says across the airwaves to the faithful RushNation that this was the "worst day of [Obama’s] presidency” and that the president had "wasted his country's time, and his prestige." Also "Obama demeaned the office of the presidency, going on this sales pitch," So, now, Obama has managed to spend political capital for nothing in return in the middle of a difficult legislative fight over healthcare reform, the touchstone of his first term, but he has also nearly destroyed the notion that when he enters the discussion that he is sure to carry the day which his detractors are busy gleefully pointing out as they play "pin the tail on the President." In a rare occurrence the President has allowed the situation to play him rather than him playing the situation. Faced with four unpleasant options that were all net political negatives, he swung hard and struck out by landing in the worst outcome available.
While it's true that this was an unavoidable no-win situation for President Obama, it is equally true that his pursuit of the least negative outcome has resulted in him fumbling the ball and now having to come to terms with the worst-case scenario: both he and Chicago have lost with no consolation prize. Perhaps the lesson to learn from this is when you're going to strike out no matter what, it is best to watch the ball pass instead of swinging so hard that the bat escapes and injures the nearest fans. Being caught looking is better than causing yourself more problems than you've already got.