The Chronicler of the Kingdom of New York: Peter Kaplan 1954-2013

(Illustration by Drew Friedman)

(Illustration by Drew Friedman)

Peter W. Kaplan, the former editor of the New York Observer, passed away after a battle with cancer Friday. He was 59. As The Observer’s editor-in-chief from 1994 to 2009, Kaplan took a paper with a small circulation and revolutionized the field of journalism, whether people knew it at the time or not. He crafted a voice among his writers that was in turns sophisticated, sarcastic, erudite and honest, a legacy that can be seen nearly everywhere in media today. The writers and editors who came of age under Kaplan represent a veritable checklist of journalistic success stories, including the gossip columnist Frank DiGiacomo; the New York Times editor Alexandra Jacobs; the New Yorker staff writer Nick Paumgarten; Choire Sicha, the founder of The Awl; Candace Bushnell—whose column Sex and the City, which Kaplan named himself, became a pop culture sensation even as the paper that printed it remained relatively obscure; and scores of others. There are few publications in New York City—either extant or extinct—that do not bear at least some of his influence.

Writers talk about the old Observer as if it were a sacred religious text. Under Kaplan’s tenure, the paper became nothing short of the best kept secret in New York. Its subscriptions never rose much above 50,000–this is true to this day; a spike in circulation, as one former writer speculated, was likely the result of a new crop of young talent moving to the city to try to make it in media. Still, the influence the paper had among the people who controlled the power in New York was incalculable.

“The paper got talked about by the people in New York who do the talking,” said Michael M. Thomas, a columnist who predated Mr. Kaplan, having been around for The Observer’s founding in 1987. “I remember once I wrote something in the paper and it irritated Jimmy Robinson who was then the CEO of American Express. And he called me up and yelled at me and I said, ‘For chrissakes Jimmy only 12 people read this newspaper.’ And he said, ‘Yeah and I’ve heard from all 12 of them.’”

Kaplan was born in Manhattan and grew up in New Jersey. His childhood hero, according to his brother James, was Popeye. By his teens, he transitioned to FDR. He went to his first presidential convention at the age of 16 and, his brother said, never missed another after that. He read Theodore White, Joseph Mitchell and especially Robert Caro with great attention. He attended Harvard and worked for the Crimson, both as an editor and cartoonist. (John Updike visited the Crimson offices one day and Kaplan drew his caricature. Updike signed it with a note: “This looks like me, I’m afraid.”) After college, he held a succession of impressive jobs: a reporter for the New York Times; the executive editor of Manhattan Inc.; and executive producer of the Charlie Rose show.

Much of his reputation, though, rests on his 15 years at The Observer. He was responsible for the paper’s look—its pink pages and hyperbolic caricatures made it look something like the New York Review of Books in drag. A skilled drawer, Kaplan gave over each week’s Observer cover to illustrators, commissioning the art himself. As an editor, he was legendary, his talent matched—according to those close with him—only by his personality. It may have taken a while for some of his staff to realize it, but he wore the same uniform everyday: tie, usually tucked into a blue oxford shirt (to avoid ink stains), navy blazer and khakis. His glasses were always filthy. Time management was not among his many skills. He commuted to The Observer’s offices from Larchmont, and stayed late most nights. His office was like the site of some horrendous natural disaster. His maxim was: “Sensibility is cheap. Reporting is hard.”

The man seemed to effortlessly cultivate his own mythology. Among Kaplanites—several referred to themselves as that—stories circulate like currency: a few mentioned how he lied about his age and held down a staff job at a radio station as a high schooler, until they got a good look at him. Others brought up, as if it were an old fable, how he and his brother James were living in Hollywood and were tapped by Peter Bogdanovich to write the sequel to The Last Picture Show, an experience that likely drove Kaplan back to New York with more ambition than before. (This, it turns out, is partly true. The brothers Kaplan sold an original screenplay to Warner Bros. in 1983 called Native Genius, according to James. He described it as a “Capra movie in a sense,” about a guy from middle America who invents a car that runs on hydrogen fuel cells, moves to the big city, almost gets corrupted, but doesn’t. They were assigned Mr. Bogdanovich as a director, who was bracing for a comeback. “For about six months in the 1980s,” James Kaplan said, “we were the first draft of the Coen brothers. We were hot in Hollywood. Everyone wanted us. It didn’t really pan out.”) Nancy Butkus, Kaplan’s longtime artistic director (they met in 1984 at Manhattan Inc.), described him as “the master of ceremonies” at editorial meetings every Wednesday morning. “You could have sold tickets,” she said. George Gurley, a former staff writer, described him as “the general or the coach. Like Vince Lombardi or Henry V.” Arthur Carter, the former owner of The Observer who worked closely with Kaplan and granted him a kind of carte blanche, said of the editor, “I’ve never met anyone who had the combination of intellectual brilliance and kindness to everyone he dealt with,” a sentiment that was echoed by everyone who knew him.

“Walking down the street with him to get coffee could be a chore,” said Tom McGeveran, the editor of Capital New York, who took over The Observer as interim editor when Kaplan left in 2009, “because he wouldn’t walk on sidewalk grates or under awnings. And he also couldn’t allow a beautiful woman to walk by unnoticed.”

He could exhume whatever was novelistic out of any story, whether it was a 3,000 word profile or a short item. His goal was for writers to talk about what their subject ate for breakfast without losing sight of the big picture. The New York he chronicled with his staff at The Observer was one of essentially comical wealth and power. In a New York magazine piece commemorating the tenth anniversary of September 11, 2001, Kaplan described the “almost pornographic response” readers had to the paper’s weekly coverage of gaudy real estate transactions. The headlines, most of which Kaplan wrote or rewrote himself, frantically dictating to Ms. Butkus on Tuesday nights before the paper went to the printer, were the stuff of good farce. Here’s one random example: “Acid Reflux, Chic Gastric Ailment, Replaces the Ulcer—Ask Gandolfini.” How could you not keep reading?

Whatever reverence The Observer’s devoted following had for the paper, The Observer’s staff had—and has, still—even more reserved for Kaplan.

“He inspired in me, and other people as well, a completely blind loyalty,” said Adam Begley, the paper’s former books editor, who described Kaplan as “the only boss I’ve ever had.” Mr. Begley got the job one day when he went to the office to visit Kaplan’s assistant, Deirdre Dolan, with whom he was friendly. She asked him if he wanted to meet Peter, and he walked out of the office as the paper’s book reviewer. “The first time I met him,” Mr. Begley said, “I thought to myself, I don’t think I can ever have a conversation with this man. He had the most elliptical way of talking you could possibly imagine. It just went in every direction except to the point. And there were these huge long pauses. He would go: So,” and here there was a long silence, “and then,” another silence, “a minute would pass. And you would think, I can’t do this anymore. And then he would say something absolutely brilliant and startling. I went from thinking I don’t think I can ever have a conversation with this man again, to thinking, I always want to hear this man talk. And he never got any better at stringing together sentences. He dealt with people who were intensely verbal who were all dying to fill in his pauses, but he could suspend you.”

He also knew more about any reporter’s beat than the reporters themselves. When he took over as editor after Susan Morrison in 1994, he had a reputation as something of a cultural aesthete. Terry Golway, then The Observer’s politics reporter, was initially unconvinced. He grilled him on Al Smith, New York’s governor in the 1920s and the lifeline for many of Robert Moses’ early public works projects, thinking he’d have his new boss stumped.

“And of course he and I got in a half-hour conversation about Al Smith and Robert Moses and FDR,” Mr. Golway said. “That’s when I knew I would love this guy. He could go from talking about City Hall to talking about Broadway and be smart about everything.”

“Encyclopedic” is a word many people used to describe his knowledge. Elizabeth Spiers, a founding editor of Gawker and former editor-in-chief of The Observer, recalled phoning Kaplan “the second I got The Observer job” and “begging for his advice.” He asked Ms. Spiers where she was from.

“And I said, ‘I don’t think you’ve ever heard of it. It’s a rural town of about 2,500 people in Alabama called Wetumka. And he said, ‘Oh I used to live there.’ I thought he was bullshitting me, but then he proceeded to describe the back route of how to get to Wetumka from Montgomery in great detail. His roommate at Harvard was Bobby Kennedy Jr. and apparently they both decided they would write their theses on civil rights, so they moved to Montgomery for a summer.  He started listing off the names of people my parents would know. It just seemed so appropriate that he would know more about the little town that I was from than I did.”

The “days of wine and roses,” as Tom McGeveran called them, of Manhattan media in the late 90s were over long before Kaplan left The Observer. In his last years at the paper, he navigated a number of issues that continue to plague the industry—namely, endless budget cuts and the digitization of the news. He can be known as somewhat musky, a relic of a bygone era, but he embraced this new frontier gracefully.

“He used to say, ‘Everyone’s trying to find a life on Mars on the web, but we need Saturn. We need Jupiter,’” Mr. McGeveran said. “I think a lot of editors were afraid of it, but I don’t think he ever was.”

“Peter Kaplan was a partner, a mentor, and a friend,” said Jared Kushner, The Observer‘s publisher, who bought the paper in 2006. “Others have said that Peter saw The Observer as one big ongoing novel. If that’s true, then no editor ever did more to bring that story’s characters vividly to life. Peter was a great editor.”

Kaplan stayed on until 2009, relaunching The Observer from a broadsheet to a tabloid format, and making sure the publication lived through a tumultuous recession. His name remains synonymous with the paper he edited for 15 years.

“I feel Peter Kaplan’s presence in this office every single day,” said Ken Kurson, The Observer‘s current editor-in-chief. “Coming here to sit in what I still consider ‘Peter Kaplan’s chair’ I have daily WWPD thought balloons form above my head. I think I would have been weighed down by it, even intimidated by that presence, except for the fact that Peter himself was habitually generous with advice and suggestions and encouragement when I started. The city has lost a very good man.”

After leaving The Observer, he became the editorial creative director of Conde Nast Traveler, though he is notoriously averse to travel. (Eventually, he was told that if he wanted to work there, he had to leave the country at least once; he chose Bermuda, and the article he wrote has the classic Kaplan headline, “Bermuda Schwartz.”) His last role was as the editorial director of Fairchild Media, where he recently helped relaunch the men’s lifestyle magazine M.

He is survived by his brothers James and Robert; his wife, Lisa Chase and their son, David; and three children from his previous marriage to Audrey Walker, Caroline Kaplan, Charles Kaplan and Peter Walker Kaplan.

The writers he worked with went on to great things, but we’ll never know what Kaplan would have accomplished outside ofThe Observer if given more time. He was a thoughtful editor who valued prose and diligence in an era now marked by viral videos and breaking tweets. He left his mark on so many people, though, it’s not exactly accurate to say he was a holdover from a different time. Those who worked with him won’t forget the frantic closes, trying to beat the New York Sun to the printer, fiddling with a subhead until the final possible moment.

“Peter just thought that if it wasn’t a mad dash at the end,” said Mr. McGeveran, “and if you weren’t an editor who was still worrying over a single word in the headline on the front page, then what on earth are you doing with yourself?”