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Peter Kaplan, an editor who defined an era of New York City publishing, died Friday night. The cause was cancer, his brother told The New York TimesHis death at age 59 came as a shock to many admirers since his illness was not well known outside of a close circle of confidants.

Kaplan, who most recently had been the creative director of Fairchild Publications, had many stops during his career — Esquire, The New York Times, the Charlie Rose show, Condé Nast Traveler, and short-lived business magazine Manhattan, inc. — but he will always be best known for the fifteen years, from 1994 to 2009, that he edited The New York Observer.

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Kaplan trained journalists to harness their voice and write with an unimpeachable wit. He filled his paper with writers like Candace Bushnell, whose Sex and the City column would inspire the HBO show, Philip Weiss, Joe Conason, Ron Rosenbaum, Rex Reed, Frank DiGiacomo, Terry Golway, Alexandra Kuczynski and trusted lieutenants Jim Windolf and Peter Stevenson. Observer alums are scattered throughout the media landscape: Alexandra Jacobs, Jim Rutenberg, Lorne Manly, Landon Thomas at The New York Times, Nick Paumgarten at The New Yorker, Andrew Rice and Carl Swanson at New York,  Jason Gay at The Wall Street Journal, Choire Sicha at The Awl,  Tom McGeveran and Josh Benson at Capital New York, Ben Smith and Doree Shafrir at BuzzFeed, John Koblin at Deadspin, as well as writers like Rebecca Traister, George Gurley, Andrew Goldman, and Spencer Morgan. (Gabriel Snyder, editor of The Wire, started out at The Observer, too.) 

Kaplan's New York City was a vibrant, powerful place, whose characters and energy, from Wall Street titans, showbiz stars, politicians, real estate developers and media creatures, sketched the 20th century. Kaplan was "regarded by those who knew him as a throwback to an earlier age — to the New York of the Stork Club, the Automat and the Algonquin," as The Times' Margalit Fox put it in her obituary. Many of Kaplan's former proteges heralded his recent editor's note for M magazine, the men's fashion title he relaunched for Fairchild in 2012, as "real Peter Kaplan writing":

It is often hard for me to reconcile the New York City of 2013 with the grainy brown-and-white images of my childhood—when the city seemed to be a clogged network of narrow streets and ancient restaurants with broken fizzing neon lights, often missing a letter.

Kaplan cherished power, "paying homage to Gotham’s elite even as it tickled the feet of the city’s titans," as Nathan Heller wrote in The New Republic last year. "The vigorously reported, tart-tongued coverage of New York’s power elites that Mr. Kaplan helped bring to The Observer prefigured the work of many websites devoted to politics, culture and the press," wrote The Times' Margalit Fox.

Heller drove around Kaplan's neighborhood with the former editor, talking about life with the man who embodied print media more than anyone. Kaplan told Heller about an ugly stretch of high-rises he wanted to "dynamite," that ruined his view.

Known for his years spent as an editor, Kaplan was also a stunning writer, with an unforgettable eye for English and its many hypocrisies. "The barefoot contessa wore rubber thongs," begins a famous Ava Gardner profile written by Kaplan for The New York Times

I don't know why I'm still bothering you with my words; I never worked for Peter and did not know the man. He was a personal hero, a man made a myth through whispers, New Republic profiles and cranky, wise impersonations online. We spoke on the phone once about the fate of those Twitter accounts; he was everything in that 76 seconds people say he is. M is my favorite magazine.

So you should be reading something from the Longform selection of Kaplan-related work. You should dedicate time to his essay on New York City before and after the September 11 terrorist attacks, written for New York Magazine's 9/11 anniversary issue. You should dedicate time to the oral history of his New York Observer tenure. You should dedicate time to the Slate and Village Voice essays, written in 2010 but just as important now, about his many parody Twitter accounts, in all their cranky, wise and real glory, run by Windolf and Stevenson.

But you should really read "Never Hold Your Best Stuff," the essay written by Kaplan after the passing of his own former editor, Clay Felker. 

This article is from the archive of our partner The Wire.

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