06/25/2007 11:58 am ET Updated May 25, 2011

How Obama Ruined My Crush On Obama

The last thing I expected to feel after a night with Barack Obama was underwhelmed. Friday night's GenerationObama fundraiser appeared to be the perfect, relatively affordable way to step for a moment into the magical world of OBAMA; to stand side by side (or at least in the same large room) as the real thing. Barack with me tonight!

I don't think I was alone in my thinking and it's hard to imagine that Obama could find anywhere a more willing audience than the five hundred or so young Manhattanites who paid a hundred dollars to listen to him speak on Friday night at the Hammerstein ballroom. Should a movie producer ever be required to cast the scene the inevitable glamour of Hollywood would not stray greatly from overall appearance of said crowd, who showed up well-heeled in their business and cocktail attire, ready to impress and be impressed, all while dipping their toes in the rush that is Obama.

But then Ben Harper took the stage with an earnest blend of acoustic tunes that strayed dangerously close to sounding like a sixties protest singer; if there is a problem that Friday night's crowd faces, it must be that our relatively comfortable lives leave us too little to protest, and Harper's earnestness was, alas, somewhat lost on the room. This was the sort of Daily Show-watching crowd where, had he broken into an acoustic version of the recent YouTube sensation "I've Got A Crush on Obama" he might have left the stage with more credibility. After all, ring tones notwithstanding, this is supposed to be a different sort of campaign. But no such luck.

Shortly thereafter, against the backdrop of a huge American flag, Obama took the stage. There is no arguing that Obama has got "it." He oozes it. And in person he comes across as more forceful than his televised appearances would lead one to believe. However, as his speech progressed it felt more and more as though we were watching him on television; there was simply no gesture on his part that suggested he knew where he was, or to whom he was speaking. If one was to judge by the speech alone -- more or less, a patchwork of familiar stump speeches that anyone who has been paying attention to his campaign thus far (and believe me, that included everyone in the room) had heard before -- it would have been easy to draw the conclusion that he was anywhere in the country.

The thing is, he wasn't anywhere in the country. The group of people who came out on Friday, represent a strata of young professionals in New York who are accustomed to a certain level of access. This was an audience that is capable of big gestures, the kind on whom the list of local grass roots groups handed out at the end of the night was rather lost. It was also an extremely media-savvy audience that, put to use, could be reasonably influential on just the bracket of internet-friendly, under thirty-five voters that Obama is so appealing to. This was not an audience that needed to be lobbed familiar platitudes. But you'd never guess that from what Obama was saying.

Not that there was anything to argue with in his speech. However, an awareness of time and place is the corner stone of good campaigning. Is Manhattan really the best place to go on about gas taxes? And yes, while it might be hard to find a more concentrated bunch of Bush haters, to say that we are all frustrated because our politicians are doing nothing is widely missing the mark in a city that loves its nationally active mayor and just this week is boasting a possible trifecta of Presidential candidates. Not to mention a Senator who has spearheaded the charge against Attorney General Gonzales, and a Governor who was elected primarily because of his headline-grabbing tenure as state attorney general. We all have our gripes, but New York City is certainly not suffering from a lack of active politicians.

Furthermore, there was no mention of 9/11. Certainly no one wanted to hear the Giulani treatment, but to skip it entirely? This is obvious stuff here; it is impossible to imagine Bill Clinton (or Hillary for that matter, or even Bloomberg) addressing Friday night's crowd and mistaking it for pleasant crowd somewhere in the middle of America. It should have been seen for what it was, a privileged, connected, capable and somewhat cynical group that was excited enough by Obama to spend a Friday night in midtown with him. This was an audience that should have been taken full advantage of. Opportunism, after all, is a trait New Yorkers have been known to reward their politicians for possessing.

I happen to think this was also an audience that should have been challenged. Obama would have done well to walk on stage and pull his own version of Kennedy's inaugural "ask not" speech. Something along the lines of: what I see before me is a group of educated, media-savvy, influential voters who do not need me to tell them that a gas tax is necessary, or that health care should be available to single mothers in Harlem. A group who is just as much a product of the best that this country has to offer as I am, and while I appreciate you spending your money to come here, I should not be a cocktail party conversation piece. The onus is just as much on you to change things as it is on me. If you think I should be president you should put your unique positions to use." Or something like that.

What was the point of taking the time to address Friday's kind of audience if not to take advantage? Certainly not the fifty thousand or so that was raised, not when the payoff could have been so much more.

That said, even though Friday's appearance was a disappointment, I don't regret the money spent -- I'd consider spending it again. I want Obama to be everything we've been led to hope he is. However, it was worrisome. The room Friday night was a target so easy that a blind man would have had trouble missing it, and yet Obama did.

The apologist argument right now for Obama is that it is still early days. But next week is July, and the "early days" are numbered. Talk that Obama is running a traditional campaign, lacking the innovation and substance he has led people to expect, is on the rise and one can only imagine what a little bit of originality on Friday might have led to in terms of coverage. At the end of his speech, Obama threw in his sole New York anecdote about spending his first night in NYC sleeping in an alleyway, "New York will give you a lot of stories," he said. Unfortunately, the crowd on Friday was left with very little to that end.