Graydon Carter, who for a quarter-century has courted, cajoled, calibrated and occasionally caricatured an establishment he in his salad days once ruthlessly mocked, is outtathere. The editor of Vanity Fair magazine since 1992 announced Thursday that he will step down in December, vacating one of the most high-profile jobs left in the churning universe of magazine journalism, where the cultures of celebrity, politics and the arts uneasily mix.

Canadian born and originally bylined with an E. in front of his name, Carter, 68, has parlayed his position with entrepreneurial flair, developing side careers as Hollywood and Broadway producer (The Kid Stays In The Picture, Gonzo, I’ll Eat You Last: A Chat With Sue Mengers), restaurateur (New York buzz magnets the Waverly Inn and the Monkey Bar), author (What We’ve Lost), major domo of Hollywood and Washington’s most storied parties and, especially since the 2016 U.S. election cycle, relentless political gadfly and epistolary abuser of Donald Trump.

Those diversions notwithstanding, Carter has navigated Vanity Fair through changes in the business of journalism that have defeated many a competitor, shaken Condé Nast to its roots and seen lesser publications under the same roof disappear under the gimlet eye of its deceptively deshabillitated chairman (now emeritus) S.I. Newhouse. With his colleagues Anna Wintour, at Vogue, and David Remnick, at The New Yorker, Carter eventually embraced the digital age, overseeing rapid-action websites that added value to the print editions while urging their brands into ancillary businesses.

Carter also expanded the platform he inherited from Tina Brown, the savvy British editor Newhouse brought in to revivify the gasping title in 1984. (Disclosure: I’ve written for Vanity Fair, and my former wife was a long-time contributing editor under both Brown and Carter.) They benefited from changes already upending the newspaper business. With advertising cash infusions from the entertainment and fashion industries, Brown, Carter and a handful of other chief editors were able to pay top dollar for serious journalists who added Pulitzer Prize- and National Magazine Award-winning cachet to the titles. Among the writers Carter brought to Vanity Fair were Bryan Burrough, Sebastian Junger, Christopher Hitchens, William Langewiesche, Cullen Murphy, Donald Bartlett and James Steele.

Carter’s reign has not been without its controversies, notably in 2005, when a British court awarded director Roman Polanski £50,000 in damages for libel resulting from a 2002 story by A.E. Hotchner.

Carter arrived at VF after a stint as editor of the New York Observer and, most famously, as co-founder and editor, with Kurt Andersen and Tom Phillips, of Spy magazine, scourge of LBO kings, masters of the universe, the mainstream press and, especially, the “short-fingered vulgarian,” Donald J. Trump. Carter, who declared the 9/11 attacks “the end of irony,” unembarrassedly embraced the irony of his own C.V. An affection for nostalgia and pop history informed many of the magazine’s back pages. Vanity Fair‘s celebrity covers, he averred, were just so much shiny wrapping to entice newsstand oglers into paying for the serious stuff inside.

“Wonderful amalgam or cognitive dissonance?” the late Times media columnist David Carr once wrote. “However you view the current cultural conversation, some of the blame can be traced to Vanity Fair. We are either a vacuous people who can occasionally be seduced by a big narrative about the Asian flu or we are a serious people who occasionally need to read about what Gwyneth really thinks. Either way, Mr. Carter is editing a magazine for both sides of the brain.”

Who will step into Carter’s very expensive shoes, knows God. The selection process undoubtedly will provide entertainment for the chattering classes in the weeks ahead.