This story is over 5 years old
Tech by VICE

Oh Kaplan, My Kaplan!

A former intern remembers the editor of novelistic New York journalism, who inspired a generation of writers and launched a thousand fake Tweets.

Dec 13 2013, 7:50pm

On the legacy and obsessions of the last great pre-Internet editor, who died last week at 59.

If anyone knew the real Kaplan, it wasn't me. I was only a summer intern at the New York Observer when he was editor there; I would wonder what kind of magic (or whining) happened in his office when one of his hard-working, underpaid writers would disappear inside for half-hours at a time. I didn't know for instance that Peter Kaplan had dreamed, early on, of being a cartoonist, or that in his 20's he and his brother sold a screenplay to Hollywood about a scientist who invents a hydrogen car and resists being corrupted in the big city, with Peter Bogdanovich set to direct (the movie didn't happen, luckily for journalism in New York and everywhere). I didn't know he was friends with Glenn Close, one of many well-wishers at his funeral last week (well, no one seemed to know that; for an out-of-towner, his New York connections were unfathomable).

But I knew him just enough to feel lucky to have known him at all. Even at a distance, he looked like a rare species in an unwelcoming jungle: a man of ideas who was generous and inspiring and interesting, and not pretentious or humorless about any of it. Kaplan was a stylist, especially of himself. But his style didn't feel premeditated, just prefigured by a lost New York. Old-fashioned and madcap, unafraid, encyclopedic, goofy, conspiratorial, wise-cracking. Meandering, aloof, boy's clubbish, intimidating, but rarely impolite or mean. Peter's snark was infectious—it would cast a long shadow across the blog landscape—because it was invigorating, charming even. 

Maybe he wouldn't have fit in at the New Yorker—he said he may have ​subconsciously sabotaged his job interview there—but with his necktie and trenchcoat and big eyebrows and furtive grin he looked like he belonged in one of its cartoons. His looks and playful impudence always made me think of David Letterman (whom he loved, and once profiled), but a more avuncular, Yiddish version, if such a thing were possible. You wanted to hear him ramble. (And after he left the Observer, you could, constantly, sort of: Kaplan and his cranky, old-timey erudition inspired half a dozen parodic Twitter caricatures, a semi-inside joke by two former colleagues. What other editorial voice could do that?)

At the morning idea meetings in the paper's crowded townhouse headquarters on 64th St. the interns and the young reporters and editors would crowd around to toss out tales of hijinks in Albany or in the Hamptons or the wilds of Brooklyn into the gristmill of Peter's brain, and maybe he would say the hell with it, meaning yes, or change the subject and ask you about something completely unrelated. Any topic or personality seemed like it could be fair game—something, at least, to have fun with. (At his funeral, his brother James recalled that a few weeks before Peter died on November 29th from leukemia, the doctor gathered the family around his hospital bed to deliver the bad news. Peter grinned a little, James recalled. "Feel free to use this as material," he said.)

On Tuesday night, nearly a week after those pitch meetings, Peter tended to be camped out in front of a computer screen in his office or in the production room, with half that staff milling about, eyeing him, as he tried to come up with the rambling headlines that festooned the front pages alongside its great cheeky illustrations by people like Drew Friedman, Bob Grossman, and Barry Blitt. Watching him eyeing the screen and then the layout table, with its draft of the front pages that would be published next day, I imagined was like watching a doctor trying to save a patient. On some late nights, his sleeves would be rolled up and his arms folded and his jaw gently clenched, as he locked himself in his office or paced around a corner of the production room.

The moment was a metaphor for the week of meeting and reporting and writing that led up to it: the torturous process of edits and re-edits, idea meetings, tears, cursing and the slamming of doors. The cluttered townhouse was an embodiment of all of that; some compared it to a journalist Hogwarts. Even its salmon-colored walls seemed to be made of the paper. There was an alchemic quality to it all. The headlines were like spells. Like everything else, they were the most important thing. This was, Kaplan would say, the era of "the O.C.D. Observer." 

Obsessed, he would sink into a kind of headline trance. Anyone could shout out their ideas, but Kaplan was the captain, chasing a whale of a headline through a psychic place I imagined resembled his office, which was perpetually stacked with folded-up newspapers and books and cigar boxes and dusty bottles of half-full scotch with bows on them. The headlines would emerge, sometimes overwrought and always one-of-a-kind. 

In the summer of '01, after working with the other interns on a splashy feature on terrible internships at the city's big media companies, I was asked to fill in for Peter's tireless assistant for a week, opening the mail, fielding phone calls from exasperated writers, blocking the door to his office. And then one afternoon, in a move that seemed born out of both pity and desperation, another editor asked if I would accompany Peter up to Columbia for a lecture he was giving to the journalism students there, mainly to tote a stack of Observers (I was good at this; distributing the paper like political leaflets at Central Park concerts was practically a summer intern ritual). Of course I said yes. 

There we were one Saturday, awkwardly, alone together in his car, shooting uptown. He seemed a little worked up, unsure of what he was going to say to the students or to me or both. He scanned the windows while I nervously leafed through that week's paper, but somehow we found things to talk about, like what I was working on, and his turn as a producer on "The Charlie Rose Show." He loved television (he used to have a TV column) like he loved Hollywood, especially old Hollywood.

I cradled the papers, and put them on a table, and stood in the back of the giant lecture hall as Peter began his lecture with the caveat that he wasn't interested in talking about newspapers.

Perhaps it was already obvious but it dawned on me like a slap in the face: the Observer was no more just a newspaper than New York was just a city. By then I, who had grown up in New York City and in the paper's shadow, had come to think of the Observer—despite or because of its small circulation (always around 50,000) and non-existent profits (it lost millions every year)—as the finest-written publication in the world. The Observer couldn't be just a newspaper: no, it was more like a magazine! And along with the old movies, there were few things Peter loved more than old magazines.

I don't know if there were slides (that would have been uncharacteristic) but I remember, as he told stories about the first great American periodicals, seeing those old magisterial covers flashing before my eyes; the illustrated covers of The Saturday Evening Post, and Time, and Life, and that granddaddy Fortune, of the art deco type and the fogginess that surrounds the Chrysler Building in old postcards. The empire of Luce, the dominions of Shawn and of Felker. Ross. Newhouse. Lapham. EsquireNew York magazine in the '70s, with its verve and its pointedness, its impious investment in the city and its power brokers. Its something to say-ness. Its illustrations. The AtlanticRolling StoneVanity Fair. I was delighted to hear him talk about Spy, which I had once discovered in a dusty stack at home, like a collection I wasn't supposed to see.

He barely mentioned the Observer, but he was plotting out the referents for his own paper and his life, and its irreverence and playfulness and writerliness and relish for detail. It was all fascinating and new, this old stuff. These weren't magazines, they were monuments. Somehow it all looked magical, and Peter's point was that we were inheritors to all that.

He was talking about what was most important, about publishing as something bigger than the sum of its parts. It was about a point of view and a way of life. 

At the end, Peter asked the students about their favorite magazines, where did the future lie? What was the best new magazine out there, he asked, and called on some of the kids. There weren't many volunteers, but they might have named things that sounded impressive and literary. And then he ventured his candidate, what he called—I'm not exaggerating here—probably the Greatest Magazine Out There Today.

"O," he said. "Op-rah! The Oprah Magazine."

A sense of unease descended over the august lecture hall. There was silence, certainly. Unlikely doesn't describe this whitest man in the blue oxford and khakis with a penchant for cigars and Sondheim singing the praises of a supermarket glossy published by the queen of television. I tried hard to picture him at home on the weekend, thumbing through recipes and getaways. It didn't work. He hated travelling, and even after becoming editor of Conde Nast Traveler he would only go as far as Bermuda ("Bermuda Schwartz" was his headline for that dispatch).

And yet as he spelled it out, this was a Kaplanism—befuddling, subversive, punch-liney— that was hard to deny. O had good, solid writing, he said. And it was a great thing to look at! But more importantly, it was the only thing he could find on the newsstand, he said, that consistently had a strong voice, that knew just what it wanted to say. (This was made easier, no doubt, by its titular leader, who, Kaplan observed, appeared on every cover.) Its readership was built-in, which made for brisk business, and it commanded perhaps the most devoted of all readerships in the business.

But it didn't really matter to him what the magazine was saying, he was saying. He was talking about what was most important, the thing that tied Oprah back to New York, to the glory days of The New Yorker, and Esquire: in every which way, this magazine was about something bigger than the sum of its parts. It was about a point of view and a way of life. New York wasn't just a city and the Observer wasn't just a paper and Kaplan wasn't just an editor. It was bigger than that.

That's what journalism, magazines, newspapers, blogs, could be, whether they were reporting on the media, real estate, politics or art. If the reporting was good and the writing sublime, journalism could mean the whole thing. 

Illustration by Drew Friedman

There is no lack of point of view on the web, but there, the reporting and the writing parts tend to struggle through all the noise we're constantly making. My two summers at the Observer were in the pre-pageview era. had just launched; video was for TVs; gawker was still only a word meaning, I guess, a sort of stupified observer. Peter cherished the print era, clung to it, for the sake of journalism. When he decided it was time to leave the Observer in 2009, after nearly fifteen years, the paper's media reporter asked him how he felt. "It's as good as it gets. I had a little newspaper in New York City!" he said, like he had gotten away with something. "It's better to have a little newspaper in New York City than a big newspaper in New York City. Because then you only have to report and write for the people you care about. And nobody else."

A few months later, after he had taken a new job as creative director of Conde Nast Traveler Charlie Rose took the opportunity to interview his former producer (Kaplan is now credited as "executive of ideas" for Rose's new show). They talked about the interviewer's perennial topic of fascination: what does the internet mean? 

"I don't know what's going to happen," Peter said. "I have close friends who work in various, what I like to think of, as information supermarkets. Aggregation has undermined the American news process... It separates the news item from the news story. It's by definition a shallow landscape." 

"I have an evangelical mission to save the part of the print media that I love," he added. "Which is, to me, sophisticated, arcane, a little bit of a throwback to the '20s, but also a 21st century medium that the internet was a direct assault on." He described what that was, what the Observer was.

Peter on Charlie Rose, November 6, 2009 (Charlie Rose)

"It was an auteur's newspaper. The editors were like movie directors and they worked with the writers to do a complicated view of life in New York." Diagnosing power in the city was one of its missions, he said, but it was also, "in a weird way, meant to provide a Rashomon to the New York Times.

"And then of course the third thing," he said. "It was meant to be tremendous fun, and a reminisicence of what newspapers could be."

Peter was that to me: a reminiscience, however borrowed, of what editors could be, the fatherly editor figure I never had, and would never really have. He didn't edit the little things I wrote, that job fell to other wonderful editors. But Peter was a beacon. I remember that one of my last assignments for the paper was to report on a celebration of West Indian Day at Gracie Mansion, the erstwhile mayor's house. In lieu of a press pass (I don't think I ever saw one in the office), Peter dashed out a letter, which read, "To whom it may concern: Alex Pasternack is a reporter in good standing with the New York Observer. Please extend to him all courtesies and privileges. Signed, Peter Kaplan."

It's hard to explain the talismanic quality of this piece of paper, like a get out of jail free card, or something stolen from the Morgan Library. I imagined reaching into my bag and producing it and watching heads slowly nod and doors open. (It worked that time—I got some nice color and Mayor Bloomberg, who has his own mansion, told me about what it was like to visit the mayor's official house.) I still have the note, and I've since stolen its language for assignment letters I've written, for writers trying to get in doors far less fancy. Those lines don't say much, but they say more than enough. They came to mind recently after I read an elegy Peter wrote for Clay Felker, the legendary founder of New York, and his mentor.

His greatness may come down to at least these two things: He re-infused New York City with a sense of itself as the bourgeois capital of the world at exactly the moment the world was counting the city out. And he gave journalists a sense that they were up to the task of remaking the world. He gave reporters—Tom Wolfe, Gloria Steinem, Richard Reeves, Ken Auletta, Jimmy Breslin, refugees from newspapers and politics—the sense that they were writers who could change the world. One of Clay's great powers was that he knew that an editor's task was chest-bumpingly governmental: to make a journalist feel supported by a power greater than him- or herself.

Kaplan's Observer going-away party sounded like kind of event that one of the paper's reporters (or interns) would have loved to crash, so I took a tape recorder. The party room at the Century Club in midtown was gilded and glorious, but there was a palpable sense of faded glory. A stream of former Kaplan acolytes—people like Candace Bushnell ("Sex in the City" started as an Observer column), and Tom McGeveren and Choire Sicha and Gabriel Snyder and Tom Scocca (now editors of Capital New YorkThe AwlThe Wire, and Gawker, respectively)—all looked like they were wondering the hell what would happen next.

Tyler Rush, who managed the design and printing of the paper with a wicked wit and an Arkansan unflappability, praised the man whose headlines he laid out every Tuesday. "He can make even someone as cynical as me like New York," he said. George Gurley, the longtime Observer reporter, recounted with some ruefulness the time Kaplan tossed Gurley's keyboard out the window, because apparently it "wasn't being used."

"I'm always seeking his approval," Gurley said. "It's not like every time I did a piece he would say, 'great story.' But the half a dozen times he did, it was... I don't want to simplify it or reduce it," he trailed off. "Look, I need my therapist to work me through this. It might take the rest of my life to really figure it out. Imagine someone having that much of an effect on you. In an ultimately good, inspiring way. He's just a genius and not just a journalist."

Near the door was a table piled with copies of a faux Observer, full of dozens of Kaplan appreciations from his reporters, as well as people like Bogdanovich, Tom Wolfe, and Mayor Bloomberg. It was printed in the paper's new shrunken tabloid size, but designed to look like the old broadsheet. Nearby, I spotted Gay Talese holding a drink, looking less glum than the others.

"He has a kind of detachment with regard to the city and its power-brokers and its shakers and its fuck-ups," he said about Kaplan. "He really has a very eclectic vision of who runs and doesn't run New York. He has a great eye."

Talese mentioned a string of famous magazine editors from the past, and threw Kaplan in at the end. "He makes people feel young, even an emeritus journalist such as myself, because he brought a spirit of New York that no other paper had brought."

He wanted to be optimistic about the future, he said, pursing his lips. "I am so hopeful that it will continue even without Peter," meaning the Observer and its brand of journalism. "I think what he did when he was there has influenced so many people that the lessons have been learned."

A beat later, he added: "I am not one of those who's pessimistic about print!"

This was 2009. Rumors of a print apocalypse, not to mention other calamities, were fresh in the minds of many people at the party, not least the guest of honor. In the years that followed, Kaplan himself would go on to praise web publishing and the iPad, even if it sounded conciliatory, even as the Observer shrunk (this week, news comes that the paper is preparing to change its format again, and, most shockingly, will lose its old-timey logo and famous pink hue). But Kaplan was an irresolute defender of the kind of journalism print represented. (2009, before today's internet, was also a time when people still read things.) When he arrived at M, the last magazine he would direct, Kaplan proudly pointed out that its paper stock was like the kind Henry Luce had used to make Fortune. "A tactile magazine is meant to get beat up and carried around," he wrote in his editor's letter. "If it gets dirty and scuffed, good."

Finally, after everyone had had a few drinks, Peter got up for one more speech to his crew. "Sometimes I think now, I don't think print has ended, I think it has many great eons to go," he said. "But the Observer was a punctuation on a certain era of print I think," he said. "We took care of things, we named every square inch of the paper, and identified with it."

"If The Observer is anything it's a battle for New York," he continued. "It's the fight for wit, for integrity, for real reporting, for real writing, and for not killing stories even when they irritate the publisher. A fight for the New York idea."

Afterwards that publisher, Arthur L. Carter, got up to speak. In the melee of the recession he had sold the paper to Jared Kushner, a young guy with a more business-minded agenda. I had rarely seen Carter before. He gestured back to a New York of change and openness, and to a pre-9/11 New York, "consumed by overreaching excesses in taste and money," hypocrises the Observer relished exposing. He said he would miss all those years with his editor, whom he called his soul mate. "It will never be the same!" he said.

Kaplan demonstrating "the proper Carson/Letterman pencil trick" (Greg Watermann)

I wrote up the party in the style of the fly-on-the-wall society dispatches I'd learned to do as an intern, but I couldn't find an editor who wanted it (figuring they wouldn't be interested in the nostalgia, I didn't send it to editors at the Observer). A little while later though, I wrote Peter an email, proposing that I pitch some stories for Traveler. I saw it as an excuse to send him what I'd written.

He wrote back quickly. Of course I could write!—I could practically hear him saying it—but the question was, was there money to pay me! The other part of the letter was more important, and I think the only bit of writerly affirmation I ever got from Peter. "It was really nice, and made me good and weepy," he wrote.

Reading that now, thinking about all I gleaned, all I missed, I feel that way too.


Thanks to Lizzy Ratner for the headline, and to all the good Observerers.