When Nike plunked down $305 million for a slightly down-at-the-heel Converse in 2003, it tasked David Maddocks with getting the brand back in the running. (He did, helping to increase sales sixfold.) And so two years ago, when the 87-year-old footwear brand Cole Haan needed a refresh, Maddocks wasn't surprised when his phone rang. After all, he was Converse's CMO when the brand was bought by Apax Partners, the same venture capital firm that bought Cole Haan from Nike. But while the two jobs have some similar elements, Cole Haan lacks a hipster, rock 'n' roll past. It does, however, have an American past, and Maddocks has pioneered a variety of ways to send that message—from launching a documentary called the American Dream Project to melding traditional looks with high-tech engineering in Cole Haan's ZeroGrand shoes. We caught up with footwear's turnaround man in his New York office.