Peter Kaplan

The Cranky Wisdom of Peter Kaplan

New York’s last romantic gets his own magazine.

• Nathan Heller
• September 14, 2012 | 12:00 am

CLAY MCBRIDE

ALMOST EVERY DAY for several decades, Peter Kaplan, the former editor of the New York Observer, has dressed in the same outfit before departing for work. There is, surely, a shade of Harold Ross in his round, tortoiseshell spectacles, a hint of the Depression-era newsman in his rolled-up sleeves, his tucked-in tie. But beyond those points of reference, Kaplan is just Kaplanesque. He wears pale blue oxford shirts each day because the color pleases him. He likes khaki trousers because tan is a great complement to blue. (“It happens at the beach,” he likes to say—“the ocean meets the shore.”) For years, Kaplan bought dress shoes made with steel supports, because he thought the extra weight helped tone his legs. But the shoes stopped being made a while ago, so now, instead, he wears Aldens (brown, because his mother told him black shoes look severe), except on weekends, when he dons a pair of Nikes (a suggestion from his girlfriend) and lets his blue shirt get somewhat untucked. It is not that Kaplan is naturally a stiff or stringent guy. (His office in New York looks like a paper factory after a hurricane.) It is just that he knows what he likes and thinks there’s no virtue in second-guessing what has worked for half a century and counting.

At 58, Kaplan is the editorial director of Fairchild Fashion Media, a Condé Nast family that includes Women’s Wear Daily and Footwear News. He has an aging movie star’s smooth, youthful face and, like a star, the capacity to fill a room with outsized gawky charm. When he’s feeling gregarious, which he often is, he dons a barroom grin and says such things as There ya go! and Have a ball! (The latter is the subject of much speculation among Kaplan’s past associates, some of whom experience it as a kind of hex; “‘Have a ball!’ half the time meant ‘Go fuck yourself,’” former Observer staffer Choire Sicha explains.) His verbal style includes a lot of thoughtful pauses, during which he lingers on conjunctions like somebody leaning on a walkup buzzer (aaaaaaaaaaaaaand). And when there’s irony to be detected—there always is around New York—he has a way of registering it mostly in his right eyebrow, which lifts and swags abruptly like a kite in wind. Sometimes, though, extroversion fails him and a warier, more fretful Kaplan shows through. At those moments, the blue eyes go distant, the brow knits, and the mouth droops to an enigmatic grimace. It is the face of a guy seeing something ominous from a great distance, and it gives him an aspect of quiet gravity, of deep worry roiling beneath the neat gray hair.

Because Kaplan’s style is eccentric, those who’ve worked with him have spent a lot of time studying his favorite books, his eating habits, and his tics in search of insight. “Peter has a very unusual sense of time,” Adam Begley, the Observer’s former books editor, told me. “He’s always late—and then, sometimes, shockingly early.” Some staffers used to forge memos in Kaplan’s voice, carrying a mysterious inner life to the point of caricature. That caricature has recently gone public. A couple of former Observer stars, Jim Windolf and Peter Stevenson, two and a half years ago began tweeting as Cranky and Wise Kaplan, a pair of wild and wistful characters based on their boss’s outlandish interests. Enticed largely by this portrait, much of New York’s journalism world has come to regard Kaplan as a distant but endearing uncle—quirky, steeped in lore, and something of a daemon of the trade.

It is a truer assessment than many might realize. Although Kaplan is seen (or lampooned) today as a spokesman for the hoary charms of screwball comedy and ink-stained fingers, he has also, quietly, played a big role in marking the path of digital-age journalism. It’s hard to find a major publication right now, in print or online, that’s not in some way flavored by the old Observer: Subtract Kaplan from the media landscape of the past 20 years and you lose The Awl, much of Gawker, and a good bit of Politico, too. You lose many of the most distinctive reporter-stylists at magazines like New York, favorite bylines in the Sunday Times, and even members of the writing staff of “Girls.” It was Kaplan who hired Candace Bushnell, a struggling freelance contributor, and suggested that she write her way into the mounting erotics of money and power in ’90s New York by reporting them as a narrative he called “Sex and the City.” And it is Kaplan who attended to many voices long before they started tearing down the mainstream. Nikki Finke was a Kaplan writer. So was Ben Smith. It’s not just that his spunky sensibility has seeped into the DNA of Internet prose. (Sicha, a defining voice of Gawker and a co-founder of The Awl, told me that when he sits down to write, it’s still Kaplan’s taste and standards he is trying to meet.) What Kaplan offers is an eye to the long arc of journalistic craft—a sense of how today’s reporting, form, and style compare not only to the coverage of, say, the last election cycle, but to the greater arc of journalistic evolution since the late Jazz Age.

That style of thought has made him an attractive recruit. In 2010, Sidney Harman offered him Newsweek’s editorship (Kaplan turned it down, thinking the magazine required a bigger miracle than he could offer), and Arianna Huffington has previously tapped him for the top spot at The Huffington Post (“I couldn’t get past the fact that the page evaporated every day,” he says). In 1998, shortly after news broke that Tina Brown was leaving The New Yorker, S.I. Newhouse’s secretary rang Kaplan and asked for an appointment. The morning of the meeting, his temperature rose to 102 degrees and he stumbled into Newhouse’s office sick, unprepared, and overly excited by some original “Krazy Kat” drawings hung on the wall as objets d’art. “It was the worst interview of my life,” he says; today, he thinks the fever, which vanished afterward, was like Alvy Singer’s L.A. nausea: his subconscious’s way of swatting away a job he didn’t at that moment have the will or stamina to manage.

Fourteen years later, though, Kaplan finally finds himself at the helm of a stylish New York magazine. M, which launches this month under the Fairchild umbrella, is Kaplan’s latest, proudest project: the fullest realization of his ambitions for bound print. M is nominally the reboot of a long-retired Fairchild men’s magazine called M: The Civilized Man, but the new version is a ground-up reinvention. M will appear quarterly and—unusually for a luxury-market print magazine—its editorial infrastructure is being cobbled together on the cheap: Kaplan produced the first issue by borrowing staff from other Fairchild properties, like Women’s Wear Daily, and bringing in a couple of trusted ringers from the old days, like Windolf, to help wrangle and edit stories.*

After nearly two decades of working mostly with newsprint, for a narrow audience, Kaplan is poised to make his mark on heavy paper. He’s concentrating on details to set it apart from the rest of the newsstand: three grades of paper (80-pound uncoated stock for the cover, 70-pound coated and uncoated inside—the same mix used for Henry Luce’s luscious 1930s Fortune), a selection of “real fonts” from the old days, and layouts he calls “masculine without being silly.”

“I thought there might be a place for a men’s magazine that had a different kind of voice—a much wittier, more sophisticated, grown-up voice, and that was much more a lateral conversation than trying to whack you over the head with Mila Kunis,” he explains. “I’ve got two sons who are in their early twenties, and they are culturally demanding. They have a tremendous sense of humor. They are digitally fluent and literate at the same time. They are impatient to the point of being dismissive of two-thirds of the culture that’s being foisted on them.” This new-style guy also tends to dress deliberately, with a knowing sense of fashion, and in that nexus, Kaplan saw his opportunity.

ON LABOR DAY, I met Kaplan at the corner of East 43rd Street and Lexington, behind Grand Central, to ride with him back up to Larchmont, New York, where he lives. Kaplan had been driving all morning—he had just dropped off his 26-year-old daughter at the airport—but he didn’t seem tired. It was cool out, with storm clouds riding toward the city on a strong breeze, and the streets were clear. I got into Kaplan’s compact Honda SUV and we took off northward on York.

Kaplan is a voluble talker, and his conversation tends to start with one subject and spread in overlapping branches. In the car that morning, Kaplan rhapsodizes about Dwight Macdonald (“a rigorous essayist who has a sense of humor and loves the English language”) and Evan Thomas’s new Eisenhower biography, Ike’s Bluff (Thomas wrote an essay about Eisenhower for the first issue of M), then weaves in Robert Caro’s latest volume about LBJ (“the greatest magazine profile ever written times a million”).

Also—and this is the last thing that he thinks I ought to know—the car is extremely low on fuel and may run out of gas at any moment.

“OK, we’re about to make the choice,” he says as we approach the last turnoff in Manhattan. “Left to gas, right to”—the eyebrows rise—“who knows what.”

We go right. As we idle at the stoplight, Kaplan takes up his Caro ruminations again, but drops them midsentence as a panhandler with stringy hair and baggy clothes approaches to ask for money.

“Oh, come on, lady, don’t make me do this!” Kaplan complains with an air of easy defeat. He carries a wallet, but most of his cash is stuffed haphazardly into his khakis, which means that in order to pay for anything, he must literally empty his pockets onto the nearest surface and root through the detritus. At the moment, he is sifting through a mass of crumpled paper, old receipts, and money he’s shoveled into his lap. The panhandler looks on. “God, I don’t have a single!” he exclaims. “All right, wait a minute! Wait a minute! Wait a minute!” Finally, he finds a dollar bill, and the window comes down. “There ya go. There ya go!”

“Thank you,” the panhandler says, and moves to the next car.

“OK!” Kaplan shoots back. He starts rolling up the window and turns to me. “Was that a man or a woman, do you know? Do you have any idea? Do you have a guess?”

I say a woman.

“I’m not sure.” As the panhandler passes again, he commits—“Yeah, it’s a woman”—but follows her with his eyes until the light changes. “I think.”

In recent years, Kaplan’s life has steadied somewhat from the high-strung, high-wire labors of his early career. While he spent most of his twenties and thirties bouncing from job to job, today he has something like free pasture in his role at Fairchild. Where the late ’90s were a tumultuous period in his private life (in the space of a few years, he went through a divorce, with three kids, and started dating his current partner, Lisa Chase, then an editor at the Observer), he today enjoys a placid-seeming suburban existence with Chase, their eight-year-old son, and his older children.

On the FDR Drive, he has just begun talking once more about Caro’s book when a loud phone ringer goes off, and a caller ID—“Bobby”—flashes on the Honda’s dashboard screen.

“Uh-oh,” he says. He begins rummaging for his iPhone between the seats. “I don’t know who it is. Uh-oh. Hang on. Bobby?” He begins shouting. “Bobby! ... Bobby—you there? ... Bobby!”

There is silence for a long time; then, at last, a low, mellifluous voice booms through the car’s stereo system, in surround sound. “Hey,” it says. “How’s your kidney stone?”

“I think it’s not a kidney stone!” Kaplan shouts back. “Thank you. I called the doc—I think it’s not.”

“Ugh,” says the voice.

“Listen, I’m going to try to come up to your house at around four! Will you be there?”

The voice says four is fine, and Kaplan signs off. He grins sheepishly.

“It’s my college roommate, Bobby Kennedy,” he says. “Whose bridge we’re about to get on—look, there ya go!” Before long, the RFK Bridge, rattling underneath us, has reminded him about the awesome nuance of Caro’s RFK portraiture, and he returns to the book, about everything Caro got right, as we hurl on toward the Bruckner Expressway.

KAPLAN GREW UP mostly in Northern New Jersey, far enough from the metropolis that New York represented something to be conquered but close enough that the city exerted a magnetic pull on his imaginative life. His parents, both New Yorkers, liked to steal into town for “romantic weekends”; sometimes, he and his two brothers were allowed to come along. Once, when Kaplan was four, his parents took the family to see Robert Preston in The Music Man at the Majestic Theatre. He developed a high fever on the ride into town, and when they arrived, he dragged his father into the men’s room, where he threw up through most of the overture. Later, they slipped back into the hall and watched the musical while sitting on the steps. The Majestic is a jewel box of a theater, and Kaplan, feeling purged and dreamy, absorbed the performance like a piece of cotton paper taking on a watermark.

Today, Kaplan’s cultural nostalgia is famous. It centers on the period, before the tumult of the ’60s, when the Broadway stage still marked the zenith of pop culture and the silver screen still shimmered in the public imagination. “Lots of references to Hollywood history, proper nouns, and a lot of them in a row—sometimes obscure ones,” Suzy Hansen, a former editor at the Observer, told me of Kaplan’s style both on and off the page.

“I seized on the thirties for a lot of psychological reasons, like I was desperate to understand my parents,” he told me at one point. “That was their moment.” His initial points of access to the period were also his first loves onscreen—the Fleischer brothers’ “Popeye” cartoons and The Wizard of Oz. Early on, he stumbled into the work of George S. Kaufman, through whom he found his way to Harold Ross and the Algonquin table. Ross, in turn, led him to Henry Luce—and on it went.

Larchmont itself was a show-business resort town, and as we pass through its broad streets, he takes a detour to the waterfront to try to explain why the Westchester shore has, for him, a small measure of romance.

“There!” he exclaims as some trees clear and we come to a small, crescent-shaped beach looking across the sound. He points toward the far Long Island shore. “I have one main dream in life. You see those three high-rises across? I want to dynamite them.” The towers are short, rectangular, and scarcely noticeable unless you’re scanning the horizon. A car behind us honks. “They are the one thing,” he explains, driving on, “that keeps you from being able to imagine that it is what it was.”

ON SEPTEMBER, 11 2001, Kaplan’s train from Larchmont stopped before it could approach the warren of underground track and switches leading to Grand Central. By the time he got to the Observer’s East Side offices, New York was in the throes of its greatest change in years. As Kaplan explained last year in an eloquent remembrance for New York magazine, the town’s sensibility in the late ’90s had been one of comedy and excess. He wrote, “Irony was the voice of the city—a voice easily assigned to a town without heroes—smartness without wisdom. Seinfeld’s epic whine was our ‘Leaves of Grass.’ Sincerity, purpose, emotion were déclassé. Incomes and real-estate prices climbed ceaselessly and so did exhibitionism, steeped in wealth, full of avarice without apology.” By September 12, that had changed.

As much as September 11 shook all New Yorkers, it may have shaken Kaplan personally, in part because his identity is tied so closely to a thriving image of the city. When other people saw the gritty Gotham of the ’80s, Kaplan saw the glowing center of the world. Where locals steer clear of the overcrowded, steamy Midtown streets, he walks them like a monument. In choosing between two New Yorks—the gleaming, romantic Xanadu of Broadway shows, sun-struck towers, and parkside walks or the grim metropolis of undersized apartments and trash—Kaplan openly favors the former. Driving in from New Jersey, he says, his father always hailed the appearance of the New York skyline with the same phrase: “There’s the Emerald City.”

Today, Kaplan sees this idealism not just as an affective mindset but as an editorial one, since, after all, the way that you imagine a place shapes the way that you identify its news. As a student of Clay Felker, he championed what the New York magazine editor liked to call “point of view”: the belief that writing from your particular experience of a subject was necessary not just for rich reporting and editorial honesty but because it opened up a space for bold intelligence.

On Kaplan’s watch, the Observer went full-color, gave more space to headlines and illustrations, and focused on a kind of quirky story no other paper in town could pull off. Alexandra Jacobs, now a New York Times style writer, lambasted Ugg boots (“the heinous shearling footwear—the winter equivalent of Birkenstocks—that women are wearing all over Manhattan”) and reported on the state of the then-new Condé Nast cafeteria (“The effect is slightly vaginal, accented by hanging chrome lamps which look like fallopian tubes or sea anemones”). Candace Bushnell explored “a Manhattan literary-romantic subspecies” she called “Bicycle Boys” (“Smart, funny, romantic, lean, quite attractive, they are the stuff that grown-up coed dreams are made of”). And Frank DiGiacomo wrote a moving elegy to John F. Kennedy Jr.—a profile that bears the clear trace of Kaplan’s fingerprints. (“He made the city his Forest of Arden, his Emerald City.”) Kaplan liked to describe the paper as a kind of foil to the comprehensive, earnest coverage of The New York Times, paying homage to Gotham’s elite even as it tickled the feet of the city’s titans.

Yet despite its reputation as the wittiest broadsheet in town, or possibly because of it, the Observer never had much of a mainstream following. For years, its circulation hung in the mid-five figures, a suspiciously small audience for a paper often hailed as the Sainte-Chapelle of New York publishing. “If the Observer is so great, why don’t more people read it?” the media critic Jack Shafer asked in Slate in 2006. “Perhaps because 1) they don’t know about it, and 2) it really isn’t that great. It takes nothing away from Peter Kaplan’s stunning performance as the Observer’s editor to point out that too many Page One stories start out brilliantly but peter out after the jump to the inside.” The paper acquired a reputation as a launching pad for young, promising writers but was never seen to be a career destination. “I think for a lot of people it’s up and out,” Michael M. Thomas, who wrote the paper’s “Midas Watch” column for 22 years, told me. “A lot of people, I think, outgrow the Observer.”

Still, was that, in some sense, the point? Kaplan appeared to love helping new voices take shape on the page. His main approach in cultivating young journalists was to take them seriously, both as young journalists—when kids came in to interview, he’d often ask them what sort of writer they wanted to grow up to be—and as young people trying to figure things out. Former staffers recall epic klatch sessions during which he’d inquire about their lives, ruminate about his own history, and, in matters as disparate as reporting and romance, offer advice. He was known to return phone calls unpredictably, but when he did, the conversations could run on for hours.

“In a way it looked, from the outside, like, ‘What does he do all day? He just talks to people all day?’ And yet that was his real strength,” says Jim Windolf, who decamped for Vanity Fair in 2000. “Each single person was the main person, as far as they knew, in their conversations with Kaplan.”

George Gurley, an Observer reporter who left in 2009, told me he still has trouble thinking of himself as anything but a Kaplan writer. “I have this idea that I’m just taking a sabbatical,” he says. “I’m just waiting for that call, and then I’ll come back.”

A LOT OF PEOPLE were confused when Kaplan, on the heels of his Observer run, took a job at Condé Nast Traveler, a magazine not widely known as a bastion of oppidan irreverence. They were just as baffled when, a year or so later, he moved to Fairchild and Women’s Wear Daily. To Kaplan, though, these ventures seemed a natural outgrowth of the milieu he loved: a universe of glossy magazines and little papers with big mandates. “It’s a business newspaper,” he explains, of Women’s Wear Daily. “John Fairchild, when he ran it, was this tremendously witty, towel-snapping elitist, and the paper, like the Observer, had talking headlines.”

It was also one of the first papers Kaplan ever read. “When I was growing up, my dad’s briefcase would snap open, and there were three or four things that I would always lunge for. One, weirdly, was Women’s Wear Daily,” he says. (Kaplan’s father, a West Point graduate, started out in the shirt business and ultimately led a women’s wear company.) “Another was The Newark News, which had great comics.” Gradually, he found his way to The New York Times, The Herald Tribune, and The Wall Street Journal. But he loved the magazines most of all. “He would bring home Esquire. The big old Esquire. Harold Hayes’s Esquire. The Norman Mailer–Robert Benton–George Lois–James Baldwin–Hemingway–Dwight Macdonald–David Levine Esquire. This big fucking trove would come in every month. And it had hugely witty covers that talked to you directly, and a voice. I didn’t understand half of what was going on, because it was very grown-up writing and impenetrable. But it was the closest thing I’d seen in a magazine to a comic book.”

In high school, Kaplan joined the newspaper. His older brother James, himself a fiction writer and lauded biographer, describes Kaplan as a gregarious and popular student, albeit one proudly out of step with the countercultural mainstream of that late ’60s era. It was around this time that Kaplan started taking on his oxford-khaki look, adopted in tribute to his family’s natty eye for clothing. “We have a history, going far back to our grandfather, of dressing British and thinking Yiddish,” James Kaplan says.

Kaplan left for Harvard in the fall of 1972 and quickly fell into the heady swing of the place. “I had largely inhabited what you could kind of call a David Levine universe—Lyndon Johnson, Richard Nixon, big heads, small bodies,” Kaplan says. “There were a lot of guys like that, just these huge, oversized figures.” He became a sort of protégé of Robert Coles, the psychiatry professor cum magazine writer cum social activist. And, in his spare time, he ran a film society, Herman J. Mankiewicz Pictures, with his classmate Henry Little Griggs III.

“I thought that maybe he would do something in Hollywood, but he was first and foremost a writer,” Jill Abramson, a college friend of Kaplan’s who is now executive editor of The New York Times, told me. Kaplan introduced her to Griggs, whom she later married, and she and Kaplan also worked as Harvard stringers for Time. When Kaplan was unreachable, his assignments often went to her. “I benefitted from the fact that Peter was often hard to find,” Abramson says.

Harvard in those years was a hotbed of rising journalistic talent: The Harvard Crimson’s leadership included Michael Kinsley (who went on to become the longtime editor of this magazine and founder of Slate); by the time Kaplan’s class was in charge, the paper was being led by Nicholas Lemann (now dean of Columbia’s Graduate School of Journalism). Kurt Andersen, Spy’s co-founder and later the editor of New York magazine, ran the campus humor magazine.

“It was a lot like a big episode of ‘Little Rascals’: Everyone was running around causing trouble,” Kaplan says. “Part of it was the glamour of the Watergate era, but it wasn’t just that. I’ll tell you what it really was.” He crosses his hands behind his head and shuts his eyes to tune out the surroundings. We’re in his Fairchild office, a dim, hangar-like room off the Women’s Wear Daily cubicles in the company’s Third Avenue headquarters. “An incredible fucking explosion of belief—that not only would print change society and politics but it was worth it just because the making of it and the reading of it was galvanizing.”

Early in 1974, he came to his brother James with a proposition. “Peter called me one night and said, ‘What do you think the most fun thing we could do would be?’” James Kaplan recalls. The most fun thing they could do, Peter quickly told him, would be to get a magazine to send them to Hollywood to cover the Oscars. They wrote up a pitch. Only Lewis Lapham, then the editor of Harper’s, bit. Bearing an assignment letter and $500 as their carte blanche, Peter and James and one of Peter’s college friends flew to Los Angeles. Peter loved it. He interviewed John Huston and Jack Lemmon. He went to see George Cukor at his house, a visit interrupted by a phone call from Katharine Hepburn. By the time the young reporters headed home, they had pages and pages of notes—too many. They froze at the typewriter. “It was just like the ‘Spruce Goose,’ Howard Hughes’s plane,” Peter Kaplan says sadly today. “It was too big.”

KAPLAN RICOCHETED among various magazine jobs, largely unhappily, through his first several years out of school. In the course of quitting a post as a “baby editor” at Esquire in 1980, he pitched the magazine a profile. NBC had taken a chance on a young comedian named David Letterman, a tall kid launching a new morning show.

“I spent way too much time with Letterman,” Kaplan says. “I drove him nuts. I went to comedy clubs with him, I stayed in the car with him. He was private—he didn’t like it. His girlfriend liked me”—the Kaplan eyebrow lifts—“but he didn’t. I was a fucking irritant.”

By the time Kaplan sat down to write the profile, he was feeling overwhelmed and worried he would freeze—Harper’s all over again. So he looked to his Old Masters. Taking out Gay Talese’s Fame and Obscurity, he opened to the legendary write-around profile “Frank Sinatra has a cold” and studied its form as one might study a sonnet. He noted where Talese had live action, flashbacks, biographical exposition, and the way these pieces fit together. He took his Letterman notes and arranged them according to Talese’s schema, and then ran the whole thing through the typewriter—and again, and again, and then once more. “I could see what he was doing, finally, after like twenty drafts,” Kaplan says. Esquire bought the story and gave him a TV column to boot.

Kaplan loves to write, he told me, but never felt as if he had the skill to play at the highest level—as he’d need to if he hoped to support a growing family. After joining Jane Amsterdam to make a dummy ofManhattan,inc., the spunky ’80s business magazine, he spent a bit more than a year as a TV reporter for The New York Times, but left when his wife got pregnant. “I did not want to be a Times-man with a baby,” he says. “It was not a life I wanted to live.” He ended up back at Manhattan,inc. for a while, then at a men’s magazine venture that failed. Around that time, his third child was born, and Kaplan took an editing post at Condé Nast Traveler—an ironic endeavor in certain ways, since he hates traveling and did not own a passport. In 1993, Charlie Rose asked him to be an executive producer on his show—another gig that let him get to Larchmont at a decent hour—and it was from that perch that Arthur Carter, who owned the Observer, called him in 1994.

In taking on the salmon-colored weekly, Kaplan realized he could finally be master of both his editorial domain and his schedule. “I used to say to Kurt Andersen, when he was running New York magazine, ‘Ya know, you’re driving a town car, and I’m driving a two-seat M.G.,’” he says. But “it was close to the ground, and there were no shocks. The wind was always in your face. Who wouldn’t love that?”

KAPLAN LIVES ON a leafy street about a mile inland from the sound. His house is large and well-appointed, painted pale yellow trimmed with blue, and there’s a sun porch in the front with a long driveway cutting to a spacious lawn out back. It is a house he bought with his ex-wife and the home in which he raised his children. Inside, the décor is simple and elegant. Against one wall in a small, book-filled alcove near the kitchen sits a poster from JFK’s 1960 campaign, showing the candidate with his arm around a young Caroline; “It’s okay to dream,” the caption says. File boxes are piled on one side of the living room beside the couches, which are blue and khaki colored. A Rothko print hangs at the mantle. When we arrive, Kaplan’s loquacious eight-year-old, Davey, is reading a book at the kitchen counter. His mother, Lisa Chase, who’s now an editor at Elle, is on her way to shuck corn out back.

Kaplan takes me to a garage, at the rear of the garden, that he calls his “shrine.” “It’s my old Observer office, reconstructed,” he explains. The garage has been converted into a carpeted study with bookshelves on three walls. Near one, there’s another couch—khaki trimmed with blue piping.

When Kaplan left the Observer, after a 15-year run as editor, the move seemed at once abrupt and overdue. In 2006, Arthur Carter, who had then been funding the paper at a loss for nearly 20 years, had given Kaplan two months to find a buyer before shutting the operation down. When Jared Kushner, a 25-year-old real-estate scion, emerged as the winning bidder, Kaplan was relieved—and people then at the Observer say he stayed relieved even as the paper became harder to run. “Working with Jared was making Peter crazy,” one of his editors told me. Kushner wanted to turn it into a dynamic, streamlined business and kept cutting editorial budgets; Kaplan, who famously hated to fire anyone, scaled back incrementally. A former staffer told me he thought Kaplan finally left, in 2009, partly because he knew layoffs were imminent and didn’t have the heart to wield the ax.

But there were other considerations at play, too. “It was important for me to find a way to make first-rate journalism economically viable on the Internet, above and beyond aggregation,” Kaplan had told me back in New York. “I wanted the fucking Observer to work on the Internet, and they kept strip-mining it. And it wouldn’t. It wouldn’t.” Suddenly, he drew himself up and shouted to no one in particular. “I wanted sensibility journalism to be sold, and to matter!” he cried. “OK?”

The theme of M’s first issue, appropriately enough, is “ambition.” With styled photography and pieces from veteran Kaplan writers like Philip Weiss, culture doyennes like Lynn Hirschberg, and younger Observer alumni, the issue tries to understand how the expression of American ambition has changed over the past several decades. It’s a question Kaplan has been pondering a good deal recently, in part because he’s trying to figure out where the next generation of ambitious, genre-bending journalists whose work will both turn heads and last—the auteurs of the craft—are coming from. Five years ago, he thought it was just a matter of time before this brave new style made an appearance. Now he’s not sure. “Where is the thing?” he asks me in his garage office that afternoon. He’s frowning anxiously and staring at a far wall, where an enormous Philip Burke canvas of Roger Federer rests. “Why isn’t it coming up?” I realize in that moment that Kaplan isn’t straining toward the past as hard as he is thinking of the future—that the cultural nostalgia, Larchmont beaches, 70-pound stock, and Hepburn comedies aren’t so much a plea that the old world will come back but that the new one will, finally, come alive.

 “When the Observer was cooking pretty well,” Kaplan told me at one point, “I always had the same feeling, which was that I was really lucky, because it must have been like what running a really good small jazz band in the thirties would have been like.” By then, his voice had quieted. “And I’m always waiting for the magazine where the editor is playing a song for me.”

*M’s inaugural issue will feature a spread about The New Republic; that story and this profile were conceived and reported independently.

Nathan Heller is a film and television critic for Vogue. This article appeared in the October 4, 2012 issue of the magazine.