Peter Kaplan, who died on Friday at 59, of cancer, was an editor whose career spanned and encapsulated what one of his many employees and protégées – John Homans now at New York Magazine – calls the "late Renaissance" of American journalism.  It is a career mainly associated with the New York Observer, which he edited for 15 years, but one that also tells a larger story of how the world turned in New York publishing.  Kaplan came to the city from Harvard in 1976, when print – newspapers, books, magazines – was arguably the most influential business in the city. Time, Inc was Google. Ivy League editors were princes among the mighty. He went to work at New Times, a bi-weekly feature news magazine, launched a few years before by Jon Larsen (whose father was of the Time, Inc elite) and George Hirsch, a former publisher of New York Magazine, from which all other magazines of the period descended. New York was started by Clay Felker, who all editors aspired to be. (New York, after 45 years as a weekly, has just announced that it is scaling down to a biweekly schedule.)  Single title magazine companies seemed like a reasonable model and could be found all over town – or, as it were, midtown. Who didn't want to be in publishing?  In 1976, Rupert Murdoch launched a successful hostile takeover of New York Magazine, which also got him its sister publication the Village Voice, which, at the time, had a per-line classified advertising rate higher than any other in the world. In 1982, Bill Ziff, who owned a stable of hobby and trade magazines, one floor up from New Times, sold his titles for $1bn (half of them to Murdoch, the other have to CBS because even television networks wanted to be in publishing), making magazines an official gold mine.  Alas, New Times, which lasted through the 1970s, closed because its general interest topical subject matter was not as attractive to advertisers as the new "targeted" subject matter. Indeed, New Times sister publication, the Runner, about the new running craze, was sold to Ziff, its upstairs neighbor and included in the billion dollar sale. (Ziff went on to build yet another billionaire dollar publishing company around computer magazines.)  After Felker had been forced out of New York Magazine, he bought Esquire, where Kaplan was next hired. Esquire, the dominant magazine journalism title of the 1960s, had began to ail in the 1970s, in part because the men's publishing category had become so over-crowded. Men, who currently represent a minuscule publishing audience, were then the most attractive and profitable demographic in the industry. Felker's Esquire, expanded and renamed Esquire Fortnightly, quickly faltered, and had to be rescued by Chris Whittle, a small-time out-of-town publisher, who rode a revived, if dumbed down and advertiser friendly, version of Esquire to instant power in New York.  Kaplan, who had an unhappy segue at the New York Times Magazine, went on to become the number two editor at Manhattan, Inc, a business magazine in the style of New York Magazine, launched in 1984 by Herbert Lipson, a publisher from Philadelphia, and edited by Jane Amsterdam who had worked with Kaplan at New Times – and, who, in the tight knit, incestuous, and Kremlin-like New York publishing world, married (and later acrimoniously divorced) New Times founder and, subsequently, Village Voice editor Jon Larsen.  Manhattan, Inc, covering the new money of the 80s, and, in almost sporting fashion, the rise of the exaggerated figures on Wall Street, was, briefly, the hottest spot in New York journalism life. Indeed, 1985 marked the high point of revenues in the magazine industry. It was all downhill from there, but no one knew it yet.  In 1987, the stock market crashed causing turmoil between Lipson and his editors and, in short order, the exit of Amsterdam and Kaplan. Felker would return briefly to take their place, before Manhattan, Inc closed, along with the decade. Kaplan, who returned again unhappily to the New York Times, began trying to create and raise money for his own magazine – a new, sophisticated men's title. Smart Magazine, another sophisticated men's title, had just recently been launched by Terry McDonell, a former Rolling Stone editor, with backing from Psychology Today publisher and high flying magazine entrepreneur Owen Lipstein. But when Esquire, beginning to see a drop in the market, sold itself to the Hearst Corporation, McDonell was hired to take over and Kaplan was handed Smart.  But this was 1990, and the recession that year caused a sudden retrenchment of consumer advertising spending with print suffering more than all other media. It was an inflection point from which began the great decline in print advertising. And it trapped Kaplan at a magazine that could not afford to publish – or even clean its offices (a bad fix for the disorganized and messy Kaplan).  But then in a seismic reshuffling, Tina Brown left Vanity Fair to edit the New Yorker (bought in 1985, in its last profitable year, by Conde Nast), and Graydon Carter, who had gone to edit the New York Observer after the collapse of Spy Magazine, which he founded, went to Vanity Fair, leaving the Observer to Kaplan.  The Observer, a weekly newspaper on Manhattan's Upper East Side, was an odd fish publication started by the Wall Street financier Arthur Carter, an odd fish publisher. If it ever had a hope of making money, this passed quickly and it became merely a rich man's indulgence, though never a terribly extravagant one. A shoe-string indulgence.  Its first iteration was as a small town newspaper in New York, modeled after a similar paper Carter owned in Connecticut's Litchfield Country. Then Graydon Carter (no relation), taking from his Spy experience, and ever influenced by New York Magazine, turned it into the model of reporting on powerful people in business and media – that was the newspaper Kaplan took over.  Carter (Graydon) never got along with Carter (Arthur). But Kaplan did. Kaplan seemed to understand, earlier than most, a new reality about publishing. You had to lower your expectations. It was as though Kaplan, by then having endured so many of publishing's dashed hopes and dreams, was satisfied having no horizons beyond staying within the losses that Carter would support. Ever tempted, he nonetheless rebuffed (mostly) any interest by larger titles or, later, by new digital enterprises. He tended what he called "my little newspaper".  And, for quite some time, his hunkered down or even ostrich-like approach was an effective publishing model. Employing the young and inexpensive, or the old and over-the-hill – and being himself satisfied with a modest living – he was able to put out a weekly publication with heart and imagination.  Its influence, as has often been noted, was much greater than its size, but, with a real readership in the tens of thousands, that might not be saying much. But it knew its break even (well, sometimes break even) place. And still, this was not enough. In 2006, Arthur Carter sold the paper to 25-year-old Jared Kushner, a rich man's son, who Kaplan, now middle aged, had little patience for, finally leaving the paper in 2009.  Since then, the Kaplan legend, casting him as the last of a breed, has only grown, helped by a set of Twitter homages engaged in some ultimate ironic projection of Kaplan into a world that was wholly foreign to him, and by the reverence of the many people he trained, a downwardly mobile generation of journalists who now populate the internet.  That's the way it was.
Michael Wolff: Kaplan transformed the New York Observer and was part of the city's publishing elite during the magazine era's last golden age