An outsider’s insider, ex-Vanity Fair editor Graydon Carter knows how good he had it

The retroactive FOMO flows fast and thick through “When the Going Was Good,” former Vanity Fair editor Graydon Carter’s memoir about the final golden age of magazine publishing. The glamour. The power. The boldface names.

The expense accounts.

“Extreme expense-account creativity was looked upon with the same sort of reverence as writing a particularly fine story,” Carter writes of his days at Time, where he arrived in 1978 as a Canadian pup looking to break into the American journalism business. He writes of a colleague who tried to beg out of covering a visit from the pope by inventing some conflicting family vacation plans. His editor suggested he send the family on said vacation and expense it. So the enterprising reporter had some phony letterheads printed up and was promptly reimbursed for the vacation nobody took.

It’s a funny story. It’s also emblematic of a time when magazines had money to burn and muscle to flex. There was no internet, and readers who wanted to be in the know went to these things called newsstands. At Time, Carter worked with such future stars as A-list biographer Walter Isaacson and Pulitzer-winning book critic Michiko Kakutani (“Michi” to her pals). He ate and drank well, often for free. But he didn’t fit the Time mold. “I wasn’t Ivy League — a credential the magazine put great store in — and I wasn’t as buttoned-down as some of my peers,” he writes. He was booted over to the still-barely-relevant Life, where he plotted the escape that would shake up magazines and New York.

Carter wasn’t just non-Ivy League; he never even graduated from college. There’s nothing to-the-manor-born about him; one of the book’s liveliest chapters chronicles his time working on a Canadian railroad line, sweating elbow-to-elbow with ex-convicts and other misfits with whom he developed camaraderie and a hellacious work ethic. Even when he drops names — and you don’t last 25 years as the editor of Vanity Fair without dropping names — you get the sense that he still can’t believe this is his life. You might not think of humility as a defining Graydon Carter trait, but that’s part of what comes across here.

He’s a sort of outsider’s insider, not unlike another Canadian who climbed quickly and made his bones in the New York spotlight, “Saturday Night Live” creator (and Carter confidant) Lorne Michaels. A New York native celebrity schmoozer probably wouldn’t have come up with the idea for Spy, the satirical monthly that Carter created with Kurt Andersen and Tom Phillips in 1986.

There was nothing like Spy, a deeply reported New York gossip magazine with a literary soul and a bottomless sense of mischief. Carter and his often underpaid staff came up with devilish nicknames for their primary targets. Donald Trump, then a bullying real estate player, was “the short-fingered vulgarian.” They cultivated inside sources eager to deliver dish on the wealthy and powerful. “We wanted to be outsiders on the ramparts picking off the big shots,” Carter writes. “We wanted to champion the underdog and bite the ankle of the overdog.” The only thing worse than landing in Spy was not landing in Spy.

“When the Going Was Good” is at its best when Carter is the underdog biting at ankles, or a Don Quixote who learns to tilt at the right windmills. Spy, for all its buzz, didn’t really translate to monetary reward. Carter’s detailed account of the overhead and rigorous scheduling that go into running a magazine is eye-opening, and makes it pretty easy to see why so many glossies didn’t survive the digital transition. Even when he started at Vanity Fair in 1992, Carter faced a mighty task, inheriting a staff loyal to his predecessor, Tina Brown (an insider’s insider). It didn’t help that he had ruthlessly skewered the magazine in the pages of Spy. “New editors generally mean changes, and changes can mean unemployment,” Carter writes. “When the new editor has spent the past half decade ridiculing the magazine, its senior staff, its contributors, and its house style of over-oxygenated writing, well, that did nothing to lighten the mood. I would have hated me if I was in their place.”

Of course, he did just fine. Some of the best writers in the business graced the magazine’s pages during Carter’s tenure, including Bryan Burrough, Michael Lewis, Maureen Orth and Mark Bowden. The magazine’s annual Oscar party became an institution. And boy, did the money flow. In a recent essay for the Yale Review, Burrough, whose books include “Public Enemies” and “The Big Rich,” recalls that for 25 years, Vanity Fair contracted him to write three 10,000-word articles per year — for a peak annual salary of $498,141. “That’s not a misprint,” Burrough assures us.

It couldn’t last. “You never know when you’re in a golden age,” Carter writes. “You only realize it was a golden age when it’s gone.” The economic collapse of 2008 wasn’t kind to the magazine business; nor was the social media age. Carter bristled at plans to centralize Vanity Fair management under parent company Condé Nast and then-artistic director and Vogue editor-in-chief Anna Wintour. He left the magazine at the end of 2017; in 2019 he launched the digital newsletter Air Mail with longtime friend and colleague Alessandra Stanley.

“When the Going Was Good” is catnip for those of us still addicted to magazines, who still harbor the delusion that we’ll get to that pile on the table as soon as we can. Carter seems to know how fortunate he was to ride the wave and thrive as a shot-caller back when that meant something more than it does today. The going was indeed good.

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