An Olympic Gold Medal winner like his dad, Paul H. Smart '14, Hilary gained his medal for the Stars at Torquay on the English Channel. He and Owen C. Torrey, Jr. '47 combined to win two Intercollegiate Star Class titles. Sailing was not recognized as an official sport until the spring of his senior year, he was voted to a major H in 1948 as an Olympic and college champion. As an undergraduate, he campaigned in the summers, and placed second in the world championships in Los Angeles in 1947, and then in 1948, placed third in the world in Lisbon. He was also the Harvard track manager in 1948.