Gerald Howard is the former executive editor and vice president of Doubleday Books. He has worked with writers Don DeLillo, Paul Auster, David Foster Wallace, Debby Applegate, Hanya Yanagihara, Pat Barker, Sean Wilentz, and Bill Bryson, among many others, and is a recipient of the Maxwell E. Perkins Award for Distinguished Achievement in the Field of Fiction. This essay is adapted from his forthcoming biography, The Insider: Malcolm Cowley and the Triumph of American Literature, to be published by Penguin Press in November.