Stephen started skating at age 5 because his older sister skated and because his mother was encouraged to enroll Stephen in sports for health reasons. He was inspired by watching the 1994 Winter Olympics.
Until 2009, Stephen trained in Boston and though he now trains in Wilmington, Delware, he continues to represent his home club of Skating Club of Boston.
Stephen has missed the 2010 and 2011 U.S. Championships due to injury. He returned to the ice for the 2011-12 season, winning bronze at Nebelhorn Trophy, gold at Ice Challenge and finishing sixth at U.S. Nationals.