Which is more surprising: that Robert DeNiro and his partners at Tribeca films wanted to buy the New York Observer or that owner Arthur Carter got cold feet at the last minute? The Observer, the salmon-colored, slightly skewed weekly celebration of NY’s political-society-media world and its fascination with itself, has been an anomaly forever. A perpetual money-loser, the paper is still considered essential reading to a small yet powerful audience who long to see themselves caricatured on the front page. It would have been a vanity move for DeNiro & co, akin to Harvey Weinstein’s commitment to launch Tina Brown’s Talk magazine with Hearst. Though it presumably would have cost far less.

I have no insider knowledge of Carter and what did or did not go down at the eleventh hour; I certainly have no idea why a movie star would want to own a paper, unless it’s to make sure he gets the kid-glove treatment the next time he gets divorced. But I have to admit, I would have enjoyed a slight replay of the Talk fiasco if for nothing but schadenfreude. Like many writers in New York, I have my own personal ax to grind with the Observer and like to send occasional bits of bad juju its way.

In 2000, basking in the publicity that came from having been laid off from my job as a media columnist at Salon, I heard from a former Observer reporter that editor Peter Kaplan was looking for a writer to do something media related in the paper and that I should go see him. Getting into his inner sanctum proved more difficult than getting an audience with the Wizard of Oz and it was ultimately about as enlightening. Famously forgetful and more disorganized than your average college professor, Kaplan is protected by a more professional staff and has helped the careers of many NYO editors and reporters. Despite several blown appointments and at least one missed lunch date, I persevered. When I finally found my way into his lair — a veritable rag-and-bone shop of toppling piles of books and manuscripts — he told me excitedly about a new column he wanted me to write, a compliment to their weekly media column Off the Record.

I had what I thought was a great idea for the first one: a “magazine ICU,” rounding up some publications that were on their last legs. For starters I suggested Brill’s Content, George and Talk (all now defunct) and proceded with Kaplan’s blessing. The people at the publications themselves were surprisingly eager to talk, painting a rosy picture of their prospects even as they bailed water. I turned the piece in and after some back and forth with the editor (he thought I had been too nice to Talk, which was desperately trying to get its act together before Harvey pulled the plug) he agreed it would run…soon.

Time passed, things changed. My son was suddenly having serious emotional issues and I was flying to SF every other week, trying to sort him out. I remember standing outside of a clinic that Thanksgiving weekend, where a therapist had just suggested my son be hospitalized, trying to reach Kaplan on the phone and find out what the hell had happened to my column. At that point I was concerned that the magazines in question would go out of business before the column ran. What I got from Kaplan’s assistant was the runaround. I later learned that the then Off the Record reporter had screamed loudly when he learned I would be sharing his beat, and perhaps Kaplan got cold feet himself. Maybe he just didn’t like my column. But rather than tell me or even make up some convenient lie about what might be wrong, he whiffled and waffled and avoided me until I went away, sending me smarmy a thank you email before I put in for the kill fee.

What I remember thinking that day was that I wanted to get on plane, go back to NY and break his glasses while they were still on his face, though I’m sure my frustration over my son had something to do with my reaction. Such violence certainly wouldn’t have done much for my career here, such as it is. Though it might have got me caricatured in the Observer.