“It’s dreadful,” Anna Wintour said in early October, looking out the south-facing windows of her 25th-floor office in 1 World Trade Center, which has been home to Vogue and its publisher, Condé Nast, since 2014. It’s the neighborhood she hates — corporate, sterile, and encumbered by security. She preferred the previous headquarters, in Times Square, which offered the ability to pop out for afternoon matinees on Broadway and, more important, the feeling that Condé Nast was at the center of it all. But the landlord had given the world’s glitziest publishing company a deal to move downtown, and Condé built out 23 sleek, futuristic floors as though magazines were thriving. This proved overly optimistic. 3 years later, in 2017, Condé lost more than $120M; Graydon Carter, who relished his life among the moguls and stars, a player among players, announced his departure after 25 years running Vanity Fair; and Si Newhouse, the company’s Medici-like benefactor, died at 89. Members of the old guard couldn’t help but look around the room during Si’s memorial, at Jazz at Lincoln Center, and see that it was also a funeral for the glory days of the company. As David Remnick, the editor of The New Yorker, put it to a fellow media executive in 2017, Condé was facing the same daunting challenges as the rest of the media business and seemed to be in “a dignified state of panic” as it belatedly adapted to low-margin, constantly pivoting digital realities, closed and sold titles, and underwent a “restacking” — the chosen euphemism for squeezing everyone onto fewer floors so Condé could sublet some of the fancy real estate it now realized it could no longer afford.