Shortly after I got the editor-in-chief job at The New York Observer in 2011, I had drinks with Peter Kaplan, the longest running editor of the paper, to beg for advice. Peter had been the editor of the Observer for 15 years and I had been the editor for about three weeks.
We met at Naples 45, a so-so Italian place on the backside of Grand Central filled with people who looked like stockbrokers, but convenient to Peter’s office at Fairchild. I had met Peter a few times before but most of what I knew about him came from friends who had worked for him: he was brilliant and charming and demanding and idolized by his staff. The New York Observer during his tenure was fearless and smart and its influence far exceeded its size. And you could see Peter’s fingerprints all over New York media. Peter’s people were on the masthead of pretty much every major publication and his style and sensibility were often reflected in their work.
So needless to say, I was intimidated. I had been reading Peter’s Observer since I moved to New York in 1999, and when Nick Denton and I launched Gawker in late 2002, I thought of the Observer as its only real competitor. That said, it was a completely asymmetrical competition—there was no way I could come close to the kind of work the Observer was producing.
Around that time, I began to get job offers from traditional publications and ended up going to New York. The day I got the job, I had drinks with my new colleague Deborah Schoeneman, who was an Observer alumna herself—and Peter’s former assistant—and George Gurley, who was still doing sprawling, riotous profiles of New York weirdos for the paper.
“New York magazine?” said George. “Why didn’t you just come to the Observer?”
“What?” I said. “You guys didn’t ask me!”
George then informed me that you didn’t get a job at the Observer via recruiting; you just went in and asked for one, which it would have never in a million years occurred to me to do. I do know a couple of people who were in fact recruited by Peter, but I also know several people who actually did just go in and ask. The Observer’s late production manager, Tyler Rush, moved all the way from Arkansas because he had met a woman in New York and he wanted to work at the Observer. So he moved here, marched into the Observer’s townhouse the day after he arrived and walked out with a job. So I spent the next few years wondering if I should have just screwed up my courage and asked Peter for a job.
“You should have,” Peter said, when I relayed this story. “I’d have hired you.”
(Then we both sort of acknowledged that if he had hired me, I wouldn’t be the editor of the Observer in 2011, ha ha. Which is true. I know without even having worked for him, that I would have been a Peter Kaplan loyalist and probably part of the exodus of staffers that happened near the end of his tenure.)
The irony is, I got the job in part because I made an argument to Jared Kushner, the owner of the paper, that the Observer needed to go back to the kind of stories and coverage it was doing under Peter. It had morphed into an odd crypto-business publication and it had lost a lot of its bite in the process. The paper’s tagline—“Nothing Sacred but the Truth”—had been stripped in favor of the cringe-inducing “Money, Power and the City”, and a typical feature was a softball Q&A with a minor real estate broker headlined “The Player.” The mission seemed to have changed from afflicting the comfortable to comforting the comfortable in the most shameless way possible. And it was sad to see because I remembered so vividly how great the paper had been just a few years before. I wanted it to be that paper again.
So when Jared asked me to come in to talk about consulting on the Observer’s web strategy, I told him I wasn’t interested in fixing the website because fixing the website wouldn’t fix the Observer. You had to fix the paper as well. And then I rattled off all the things that made it so amazing during Peter’s tenure. It was not intimidated by power, and it didn’t kowtow to it. The writing was sharp and witty and intoxicatingly brilliant. The paper had a distinct viewpoint and a style that was recognizable as uniquely the Observer’s.
Peter had been responsible for all of these things. I don’t know if Jared recognized the description as the exact paper he had acquired in 2006, but he found the version that I articulated compelling enough that he offered me the editor-in-chief job.
And so I emailed Peter to seek counsel. He had always been very nice to me, but I wasn’t sure how he would react to the fact that the paper was now being run by a web brat who 10 years ago might have been a very junior level Observer hire. But, as I would see over and over again, Peter was an enormously generous person. If privately he was horrified by it, he never let me see it. We met for drinks periodically throughout my tenure at the Observer and he gave me a lot of honest, unflinching feedback and good advice.
He told me that my “number two” was the most important hire that I would make because you needed someone who had your back when things went bad, and that your number two may or may not be the number two on the masthead. He stressed the importance of hiring the right people, generally—people who really understood the paper’s mission and cared about the quality and integrity of what it produced. He cautioned me about trying to replicate too much what the Observer had done in earlier years because nostalgia could be dangerous. And I could ask him point blank if something was a stupid idea, and he would tell me as nicely and warmly as possible, that yes, it was.
I could also tell that he missed the Observer. He loved the paper deeply and wanted it to retain the high standards that he had set as editor—standards I wasn’t sure I could ever hope to meet. One former staffer told me that no matter how much you knew about your beat as a reporter, Peter always knew more. And in conversations with him, I was always floored by how much he knew about… well, everything. It goes without saying that he was a voracious reader, but he seemed to absorb information by osmosis. Like all good reporters, he had a natural curiosity about things and it translated to a depth of knowledge and experience that is incredibly rare.
I felt—and still feel—some disappointment that I never actually got to work for Peter, but lucky to have been able to ask him for counsel when I unexpectedly became the custodian of the great paper he built. He was encouraging and supportive and when things weren’t working out, sympathetic. (The day it got out that I had resigned, one of the first emails I got was from Peter. One line: “Welcome to West Berlin!”) And he didn’t have to be any of those things, but it was in keeping with who he was. For all of that, I am enormously grateful.