Woodruff’s prowess as a track athlete became evident at Connellsville High School, where he broke the national high school mile record. He attended the University of Pittsburgh and qualified for the U.S. Team for the 1936 Olympic Games in Berlin. His crowning achievement was an exhilarating, come-from-behind gold medal victory in the 800m finals. Trapped on the outside, he stopped running, let everyone pass him, then used his nine-foot stride to win one of the most storied races in Olympic history.