Peter Kaplan at the Observer: An Oral History

Photo: Patrick McMullan

After fifteen years running the New York Observer, today is Peter Kaplan's final day on the job. He'll start Monday as creative director of Condé Nast Traveler. Kaplan groomed countless young journalists in his years at the Observer, many of whom now populate the city's more remunerative newsrooms. Jesse Oxfeld spoke to a number of Observer alums to create an oral history of the Kaplan era.

Frank DiGiacomo, 1993–2004: Graydon Carter, and then Susan Morrison, first turned the Observer into — let me think of a Tom Wolfean phrase — this salmon-colored Manhattan-flake streamline baby. But it was Peter, when he took over in 1994, who got behind the wheel and said, "Lemme open this thing up and see how fast I can get it going." He had real ambitions for the paper — not that Graydon and Susan didn't — but Peter really looked at it as, What can I do with this thing? How can I take this thing to the next level?

Graydon Carter, founding Observer editor: Peter is a great editor, and I thought that he would probably last a year or two years with Arthur Carter. I think it's one of his great accomplishments that he managed more than a dozen years with Arthur. He produced an original and colorful or vibrant chronicle of the last fifteen years in this city. My version was the black-and-white sketch of what he did, but he gave it color and vibrancy that I never got a chance to.

Warren St. John, 1996–1998: He has a way of taking the seemingly small changes in Manhattan media or Washington media or business and casting them in this grandiose, epic, novelistic light. You see it in the headlines in the Observer, but you also see it in the assignments. There's rich narratives in the seemingly mundane, and he'd always tell us that the Observer is a kind of ongoing novel about New York City.

DiGiacomo: It soon became evident that Peter was very much a disciple of Clay Felker. And as a result of that, he wanted the paper to be about power. That became the mantra.

Terry Golway, 1990–2004: When Susan Morrison had left and Peter had not yet come on, he left a message for me, saying, "Look, you don't know me, but I want you to know, I read you in the paper, and" — and can still hear his words, saying this — "I'm a big fan." But then his first two weeks, I was trying to get in to see Peter for the longest time, but he was constantly getting distracted. At one point I finally got my audience, and I was about to go into his office, I got a phone call from him, "Terry, I can't, er, something's come up, and I can't make it." And I slammed down the phone and I kicked the garbage can across the room.

Andrew Goldman, 1998–2000: I was coming from Boston, and I was sort of in awe of the newspaper, and I wanted the job more than anything. And because I couldn't take a day off from work or something, Peter invited me to come to Mamaroneck on a Saturday to interview with him. And he showed me around Mamaroneck and we looked at the water and we had a beautiful day together, and I loved him, and at the end of it, he looked me in the eye and he said, "I want you to come work at my newspaper," and he shook my hand. And I left there, and I couldn't get him on the phone for three months after that.

Alex Kuczynski, 1994–1997: I was like 23 or 24, and I kept sending these blind pitches to the masthead, signing them Alex Kuczynski. And, finally, after a year, Peter apparently stands up in a meeting and says, "Somebody call this guy Kuczynski." And I just love the fact that he had faith in some random person who just kept sending stuff over the transom every week for a year.

Rebecca Traister, 2000–2003: What's that thing they do in academia, when somebody retires and they put together a book of people's memories of him? There's a specific German word for that volume [Ed: Festschrift] — and I always wanted to do one of those of all the people who thought they had a job at the Observer after multiple interviews with Peter Kaplan who then arrived for their first day of work and discovered that in fact they did not have a job. You used to hear from so many people these stories about, "Oh yeah, Peter Kaplan, I had like fifteen interviews with him, and then I showed up for work and it turned out I wasn't really hired."

Goldman: Peter Kaplan's assistant sat in front of his office, and reporters, being what they are, you'll kind of look over the shoulder and see the messages. And I remember five days straight there was a message from Walter Isaacson. And he kept calling and he kept calling, and finally: "Walter Isaacson called again. He says it's not bad."

St. John: I remember one evening when I was writing "Off the Record," I had to write a front-page feature about Geraldo Rivera and how his career was being resurrected by the Lewinsky scandal. And I couldn’t imagine how in the world I was going to write this piece, I wasn’t feeling it at all. It was one of these late Monday nights at the Observer, and I went into Kaplan’s office, and he closed the door, and he sat me down, and he basically had me convinced after twenty minutes that I was writing Armies of the Night, that I was writing one of the great snapshots of our time and culture. He’s amazing in that way.

Kuczynski: I wrote a cover story about going to have an upper colonic, back when all the social people were having high colonics. And, truly, it was the most revolting experience of my life. And Peter was like, "You've got to do it for the good of the paper." And I was like, "I will have a tiny man put a garden hose up my ass for the good of the paper, yes!"

DiGiacomo: When Princess Diana died in 1997, I was in California interviewing Bridget Fonda for a freelance piece. I was also recovering from Lyme disease, and the antibiotics I was taking were almost worse than the disease itself. But Peter figured that if I was well enough to travel for some other publication, then I could write a cover story for the Observer. I got back on Sunday and knew that he wanted me to write an essay that tied Di’s death to the age of fame for Wednesday’s paper. But by that Monday, it seemed to me that everything there was to say about Princess Diana’s death had been said, and I couldn’t find anything new to write. The problem is, I waited until the last minute to tell Kaplan this. But instead of going to find another writer, he did a remarkable thing. He shut his door for like four hours — there were people waiting outside to get him to sign off on other aspects of the issue — and he just banged out this brilliant piece that is one of the best things the Observer ever published, and one of the smartest stories written about Diana in the aftermath of her death. As they used to say in my hometown, he totally knocked my dick in the dirt.

Jason Gay, 2000–2004: His gift for headlines is unmatched. Do you remember the piece George Gurley wrote about Ann Coulter, where she joked about Timothy McVeigh neglecting to bomb the Times? Peter stared at the screen for hours trying to come up with the exact right line. We'd settled on a pretty lame headline, but at the last minute, Peter's face looked like it was about to explode. "COULTERGEIST!" he said. It ran across the front page, one word. As usual, it was perfect.

St. John: When I was at the Observer, they would print out the stories on this laser printer, put glue on the back of them, and cut them with an X-Acto knife, and paste them onto this board, and put them in this suitcase that would be taken to the printing plant. So there were these nights of sitting around in the room around the laser printers, drinking beer, or worse, and gluing the paper together. And just barely making the deadline for the printing presses. There was this incredible camaraderie, and competitiveness, a joie de vivre about a racy scoop. It felt a lot more like the movie about a newspaper than any other place I’ve worked.

Goldman: I remember the office being just a very anxious place — although part of that was probably just the overcrowding in the old townhouse on East 64th Street. Whenever you hear about chimp overcrowding, primate overcrowding, and then suddenly they start pulling each other's arms off, I always think about the New York Observer. It was many privileged, overindulged, underpaid chimps around computers and eventually wanting to kill each other.

Goldman: Kaplan is a great teacher. Wednesday-morning meetings were just — they were terrifying, because you didn't want to be caught with your pants down. There was never any yelling or histrionics, but there was this fear of him being disappointed. And ultimately a fear everybody had at the Observer — which never really came to pass — of getting fired.

Nick Paumgarten, 1995–2000: Has anybody talked about his silences? Sometimes he just goes, "Ahhhhhhhhh," and stops. And sometimes he's thinking about something else; sometimes he's thinking, "I don't know what I'm going to do with this pathetic reporter who's earnestly asking for help"; I think sometimes he's thinking about actually trying to solve your problems, or his own problems — which often were the same thing. But it's one of those things, where you hear the tick of the clock, and time just sort of slows down. There's something magical about time in that office — it just sort of slows down. Was it Miles Davis who said that the white spaces around the notes are as important as the notes themselves? Sometimes those silences made the stuff that came out after the silences that much better.

Gay: There are certain things you can talk to Peter for hours and hours about. Like, if Julia Roberts is on Letterman — he could give you an hour on that alone. You might think that it's not the best use of time to listen to the editor-in-chief of a newspaper rhapsodize about Julia Roberts on Letterman for an hour. But it is a brilliant hour.

Kuczynski: When I left for the Times, he kept smacking his forehead. "Alex! Alex! Alex! You're making a huge mistake!" He has this habit of smacking his forehead. "You'll never write in the first person. You'll never write about yourself. You'll never write with color. You'll never use any interesting language. Or at least I highly doubt it." But then he gave me a going-away party, and he gave me an Olivetti typewriter. And I still have it.

Gay: There were a handful of running pranks on Peter, almost all of them performed by Peter Stevenson and Jim Windolf. One involved Jim pretending to be Peter's kids' piano instructor and demanding payment immediately for past lessons. In another they pretended to be a tree company out in Westchester, calling about a tree that had crashed into Peter's roof. They'd make Peter's assistant barge into a meeting and get him to take the call. And Peter would always wind up thinking it was a pretty good joke.

DiGiacomo: Once Stevenson and Windolf secreted something like a five-pound box of salt in Kaplan's briefcase to see if he would notice. The thing about Peter was that, except for his tie, he was extremely consistent in terms of his dress. He always wore khaki pants, a blue oxford shirt, a trench coat when the weather called for it, and he lugged around this leather satchel. I think Stevenson and Windolf were attempting to determine whether Kaplan actually looked at anything in that briefcase when he went home at night, and you should ask them how long it took for Peter to find the salt, but I think he schlepped that briefcase around for a while before he discovered it.

Gay: I remember Alexandra Jacobs and Deborah Schoeneman got him to come to a party by himself in Brooklyn on a weekend. They were so excited, like they'd caught an alligator in the bathtub. And there he was, in the middle of the party, in khakis and his tie tucked into his blue oxford shirt.

Kuczynski: Everybody was just secretly in love with him. At least, I think all the women were madly in love with him. You gotta love a guy in a blue oxford.

Gay: Alexandra Jacobs says that the Observer exists as a musical that Peter writes in his head — he does all the casting, there are all kinds of crazy protagonists and antagonists, and crises real and manufactured, but in the end, everyone goes home entertained and happy. I don't think there's a better way to describe the Peter Kaplan era.