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Let Me Tell You About the Most Heartfelt $200 I Ever Made

If New York is better than ever—and it is! It is!—why does it kind of suck?


Michael Bloomberg’s first term actually ended on February 8, 2004, on the occasion of Sex and the City’s ante­penultimate episode, not long after Samantha pretended to be British to sneak into Soho House, the then-new private club with the kitchen-sponge-size rooftop pool. This was the episode in which gauche, chain-smoking “Page Six” staple “Lexi Featherston” did some coke at a geriatric party, yelled, “This used to be the most exciting city in the world, and now it’s nothing but smoking near a fuckin’ open window,” and then took a header out said window. The “girls” went to her funeral at St. Mark’s Church on the Bowery, once known as the site of the first performance by Patti Smith and Lenny Kaye and then suddenly an HBO backdrop. Manhattan had become a stage set of itself. Carrie Bradshaw was the Bernie Goetz of the Bloomberg era, shooting at the walls of heartache, bang-bang.

The hook was baited perfectly, and now, for the first time since the O’Dwyer administration—look it up!—more people are coming here than are leaving. But if New York City is better than ever—and we think it is—then why does it suck so bad?

The money, yes. And the cupcakes, and the ATMs, and all these apartments that somehow are in clock towers, which are all also just money. Among the young set, it’s newcomers’ parents paying up at our phantom tollbooth. There is now a class of New Yorkers with the luxury of not just money but also plenty of time. Once you got a crappy coffee at the deli or you didn’t get coffee. Now the city is a wonderland of delicious pour-over. Every day is choose-your-own-adventure when you’re not dying over the rent. Now there’s a substantial population who thinks New York’s a lark, or college 2.0, or an indie-lectual Rumspringa, a lazy not so Grand Tour before packing it in to get married in Dallas. Not to pick on the millennials: The olds aren’t suffering either. Now a vast number of them pretend to live in the city while gardening at their second homes, in the sweet spread from Germantown to Ghent to Kinderhook. The result: New York has fewer who’d bleed for her. Once the city was for people who craved it with the stridency of a young Madonna. The result was entertainment, friction, mayhem, disaster, creation, magic.

This might speak more to my tendency toward bad choices, but at the time, nothing about it seemed unusual. A few years after the first World Trade Center bombing, I was broke again, and my downstairs neighbor, a piano teacher, said that he could cut me in on a deal for some extra cash. All I had to do was put on a toga and a hockey mask and listen to this old naked guy talk about his arcane Vietnam War sex fantasy while my neighbor shoved a bottle up his ass. It paid like $200. Worth every penny. Now it’s funny; now it’s emblematic. Also, please don’t do this! You can show your devotion to the big city without penetration and/or role-play.

Once there were people fishing for dinner on the broken piers of Williamsburg, then there were stalled high-rises and dust, then blossomed a bouquet of condos, ferries threading through their mirror glare. In Manhattan, a city of thoughtful analysands became a city of home-schooled cognitive behavioralists, quick to self-prescribe and quicker to diagnose one another.

Years ago, I went for a job interview with Arthur Carter, the then-owner of the New York Observer. His maid let me into his East 67th Street apartment; there was a package marked lauder in the elevator. Carter’s big interview question was “What does your father do?” Part of the excitement of the city then was that you could feel like you’d infiltrated and helped to overthrow these archaic systems, the remnants of Edith Wharton’s city, even if you had to take the gross loaner jacket at the Metropolitan Club. No one asks what your father does now. They either already know or it doesn’t matter. That, thank Emma Goldman, is done.

We installed the ethos that pedigree was over and all money was now equally valuable. The mythology of Silicon Alley was forced to coalesce for good, with City Hall’s fervor behind it. The start-up culture wars—a fresh beef with the West Coast, except boring!—intentionally pitted us against the weirdo jerks of Palo Alto. The scrunchy-face foxy Foursquare co-founders appeared in Gap ads, clad in mediocre jeans but form-fitting venture capital. You were a good person if you were an entrepreneur. You were creating jobs, until you weren’t. The big floor-through lofts of Broadway between Houston and Spring filled up with inexpensive furniture and even less expensive young people, each with a bitter mouthful of Adderall, each office bright and identical. So far, we’ve disrupted a few things, mostly coffee-related.


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