I distinctly remember the morning that Michael Bloomberg was elected mayor of New York. Two months after 9/11, I woke up in my microscopic studio apartment in the far East Village, once known as Alphabet City, and walked to work and glanced at the New York Post as I walked by the local deli. The headline declared the billionaire businessman, who had been smeared as a “dilettante” and largely written off, as the winner of the election. He beat Mark Green, a far more experienced local politician, and the favorite by all accounts, by a mere two percent.

It was a stunning upset.

I was shocked. Everyone I knew had voted for Mark Green. Most editorials had supported him, including the New York Times, which stated the case, thus: “This an easy call, Mark Green gets our endorsement for mayor….Mr. Bloomberg has run hard, but the fundamental argument behind his candidacy is flawed. He claims that as a successful entrepreneur, he is better qualified to be mayor than Mr. Green, a career politician. …” The Times editorial noted, “Mr. Green has not been the most lovable candidate in New York City history, but he has demonstrated a deep understanding of the issues, a sensible approach to public policy, and the soul of a fighter. That may be the quality he will find most useful if he becomes the city’s next mayor.”

The culture watchers at Paper magazine ran a letter from the editor written by David Hershkovits introducing a profile on Green that had gone to press before the election. The piece celebrated our new nightlife-friendly mayor, Mark Green. It read: ‘‘Mayor Mark Green. Get used to the sound of it because, by the time you read this, the former public advocate will have been elected.”

It was not to be. And in a way, it was OK. Bloomberg turned out to be a far better politician and mayor than the Times had predicted. The take-away for us, and for Barack Obama, is that almost no one saw it coming.

I find the Green upset to be particularly instructive to the Obama-McCain duel. There were a few differences. Bloomberg, unlike McCain, was no one’s media darling. When it was revealed that Bloomberg had preemptively  quit exclusive clubs, the Daily News called Bloomie’s handling of questions,  “lame and defensive.”

But like McCain, he was regularly depicted as curmudgeonly and an ineloquent speaker. By contrast, Mark Green—now the president of Air America—was often portrayed as being too smooth or slick.

Though the polls have been consistently tight, and though many handwringing pieces have tried to examine why Obama is behind, the recent polls were the first indication of serious trouble in Obama-land.
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