It takes an extraordinarily brave and clear-eyed writer to compose his own epitaph. Four years ago—four years before his death at age 59—Peter W. Kaplan did. He was speaking to the media reporter for the New York Observer, his media reporter, after he had just told his staff there that he would not be their editor anymore. "I had a little newspaper in New York City!" Peter Kaplan said. "You can't beat that."

That exclamation point was how he spoke, and the Observer published exclamation points because the voice of the newspaper—despite the words having passed through talented, headstrong individual writers and editors—was for 15 years the voice of Peter Kaplan. Listen up! He said it twice:

"It's as good as it gets. I had a little newspaper in New York City! You can't beat that. No matter who you are. I had a little newspaper in New York City. That's as good as it gets. 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."

The people who Kaplan had cared about, and who cared about him, filled the Larchmont Temple on Tuesday morning, rows and rows of extra chairs all the way through the movable partition to the far wall. The latecomers stood.

It was, unfortunately, an optimal funeral for turnout. That's what happens at 59, you catch all the generations: The oldsters who adored him as their boy wonder; the young ones who looked up to him as their rabbi or father figure; the ones at the height of their power and influence, to whom he was—what was he, even, to that cohort? Their peer, and peerless, a beloved friend and a bafflement.

Of course he had already nailed the epitaph. There was the whole temple full of writers and editors—Mark Whitaker and Richard Stengel, the former bosses of Newsweek and Time; New York's Adam Moss standing on the back wall; his Harvard schoolmate, New York Times executive editor Jill Abramson—and nobody in the room could touch him. His rabbi, Jeffrey J. Sirkman, conceded as much, in his opening remarks: "What else do we have but words?"

So the rabbi offered what words he could: In Kaplan, gone in the middle of Hanukkah, the people there had lost their shamash, the candle that lights the candles. At least one professional writer in the room had already had the thought.

James Kaplan, his older brother and a novelist, followed. "It should have been Peter talking for me," James Kaplan said, in opening his eulogy. And then Peter Kaplan did some of the talking for himself, through the elder Kaplan: The day he learned, in late November, that he was out of treatment options and that he was going to die, James Kaplan said, Peter Kaplan told him, "Feel free to use this as material."

The material! It kept unspooling through the eulogies: How a teenaged Peter Kaplan—who would later be notorious at Condé Nast as a travel-magazine editor who refused to travel—was expelled from high school in Tokyo on a year abroad, during which he also managed to strand himself on Mount Fuji. How Peter, still in college, "euchred Lewis Lapham" into sending the Kaplan brothers to Hollywood to cover the 1974 Oscars for Harper's, despite their never having written a magazine story in their lives—and how, for Peter Kaplan, hanging out with John Lennon, Ringo Starr, and Mick Jagger paled next to meeting Groucho Marx.

Naturally it would have. Kaplan's mode of outward expression was the madcap, even as his mind raced along tortuous inward courses, skirting sheer cliffs of anxiety. Life was joyous, because life might well be hellish. The whole Observer, in its classic era, was a comedic scenario: the staff, young and desperately ambitious, crammed into stairway landings and closets of its grubby, once-palatial 64th Street townhouse; the editor (invariably costumed in khakis, with a necktie tucked inside the front of a pale blue oxford) speaking in oracular mysteries and stacking headlines like champagne glasses, poured to overflowing with a flourish.

"We lived together like vaudevillians at an actors' boarding house," Kaplan wrote, in one of his rare direct addresses to the reader, when the newspaper abandoned the townhouse in 2004 for an office right below the Flatiron Building. Sometimes, after the move, people would see his figure in the distance, just stopping and tilting back his head to goggle at it, the crazy gorgeously ornamented geometry of the thing, right there. The Flatiron! Whatta town!

But the fun was immensely serious. Kaplan had a story to tell—an open-ended true novel, told serially and in parallel fragments—and he meant to encompass the city with it. The job of telling of it was an all-consuming task, and not always a delightful one to participate in. There was a reason the Greeks traveled to Delphi to talk to their oracle, rather than keeping it right there in the office and having regular meetings with it.

He could sit in abstracted silence as editors pitched one feature story after another, in what seemed to be maddening indifference, as the golden hour became nighttime outside the windows. The most experienced editors (the ones who understood that a cheery "Have a ball!" meant "Go fuck yourself") knew that the merits of the stories, as stories, had almost nothing to do with it—-that without ever admitting as much, Kaplan was thinking only of that week's scheduled cover illustrator, and what it might take to hook that particular artist's interest.

The front page was his kingdom, and he felt free to tyrannize it. After deadline, he would write an utterly crackpot lead onto a story, and leave the reporter and assigning editor to figure out how to make it true. Or he would jam an allusion to a long-forgotten Depression-era movie into the top of a piece, then demand that the most pertinent piece of news in the story somehow also appear in the same space. Editors would fume and rant behind closed doors, and on Wednesday morning they would start to hear back from readers praising those leads, the turns of phrase, everything that had seemed impossible in the harsh light of deadline.

The rabbi alluded to another Peter Kaplan story, one that had always hovered over him: How in 1998, when Tina Brown left the New Yorker, he was brought in to interview with the owner, S.I. Newhouse, for the most storied editing job in the industry—and, as the rabbi said, "somehow managed to sabotage himself." The story, as it is generally understood, was that he showed up late for his interview with Newhouse, in the grips of a probably psychosomatic fever, and told people afterward that he had spent the whole time raving about an original Krazy Kat cartoon on the wall.

And so David Remnick became editor of the New Yorker, heir to Harold Ross and William Shawn, and Peter Kaplan stayed at his little newspaper, as the writers came and went, and the editors came and went a little more slowly. Sometimes, in the middle of a particularly bad close, he would vanish. Apparently he would wander off to Grand Central, to watch the trains come and go for a while. Or he would lock himself in his office (his "tiny, neo-Collyer Brothers office," as James Kaplan described it), while the whole paper waited, to struggle privately, letter by letter, with those easy, zesty headlines. No one else could write them.

He stayed on. He stayed when Arthur Carter, the Observer's owner and founder, having unburdened himself of the townhouse, decided to unburden himself of the paper. Carter sold it to the callow real-estate scion Jared Kushner, and the madcap times gave way to a grim real-time reenactment of King Lear. The finances and sensibility of the paper were slowly crushed under the new owner's vicious blockheadedness, or blockheaded viciousness (the distinction between those two things was perhaps the only interesting mystery about Kushner), until Kaplan felt like he could no longer protect his Observer, as it had been.

Jared Kushner was in the temple to pay respects, with his jailbird father Charles Kushner, whose corrupt antics—embezzlement and an intrafamilial honeypot blackmail scheme—had once been Observer fodder. It was hard to fault the younger Kushner for showing up, but even harder to look at them.

There were plenty of other people to look at—Glenn Close, for one, to the surprise of more than a few former Observer staffers, who even still hadn't fathomed the depth of relationships and connections surrounding their boss. He would tell a twentysomething reporter to go ahead and call up this luminary or that one, and improbably the call would go through, the quote would make the paper, the whole thing coming off for reasons so occult that it was easier just to presume that the newspaper really had that power. Not for nothing, as the eulogies reminded the crowd, was Kaplan's hero the Cowardly Lion. Courage!

Courage! Peter Walker Kaplan, the youngest of the just-grown children from his first marriage, got up and—in tones of confidence and fondness—told the hundreds of people about how his father used to take them all on "mystery rides" on suburban Saturday afternoons, to destinations so anticlimactic that the getting there had obviously been the point. "Focus on the beauty of the ride he gave us," he said.

His firstborn, Caroline Kaplan, sang Irving Berlin: "What'll I do with just a photograph / To tell my troubles to?" Her voice was clear and strong, and the room overflowing with the savvy, the observers, the people who made their livings with words, could not do anything but quake.

[Image by Jim Cooke]