Before coming to "New York," Moss worked at "The New York Times", where he edited the "New York Times Magazine" and served as the paper's assistant managing editor for features, overseeing the Magazine, Book Review, Culture and Style sections. He brought to "the Times" a magazine sensibility. "Moss became a guru of this change – an anti-"Times" sort of figure in the middle of the "Times". A magazine person at a newspaper, an openly gay person in a repressed atmosphere, a mild man among bullies and screamers," described media writer Michael Wolff in a 1999 profile of Moss in "New York" magazine. When "Ad Age" named him Editor of the Year in 2001, the writer Jon Fine called the "Times Magazine" "one of the best reads in the business. Mr. Moss smartly and subtly remade the title, from its photography to front of the book, all the while navigating the internal culture of the "Times". Under his watch, it became a showcase for thoughtful, long-form journalism. Like few other magazines, it thrives a few steps to the side of celeb-saturated culture and a few steps beyond the typical political polarities.” Moss shifted the balance of writers from "Times" staffers to nonfiction writers experienced in magazine journalism. During his time there, the magazine included as regular contributors Michael Lewis, Andrew Sullivan, Michael Pollan, Lynn Hirschberg, Jennifer Egan, and Frank Rich, among others.