ESPN is famously—almost infamously—the most insular company in sports media, the product of a unique and grinding culture, sure, but also a wee bit of self-aggrandizement. ESPN executives have always displayed a certain smugness, believing that outsiders would surely drown amid the brand’s sheer deluge of obligations—half a dozen TV channels, a streaming service, a website and social, deals with all the biggest leagues, etcetera. The story of George Bodenheimer’s Horatio Alger-esque ascent from the company mailroom to its presidency is still lore in Bristol. And when Bodenheimer decided to retire, Bob Iger only trusted an inside man, John Skipper, to take over. When Skipper had to go, Iger in turn plucked Jimmy Pitaro from his management team.