Healy has had an extremely successful sailing and coaching career. He is in his eighth year as an assistant coach at Yale. Since he joined the coaching staff, Yale has won eight National Championships, five Ivy Championships and produced over 20 All-Americans.
As a junior Healy was a member of the International 420s world team numerous times as well as the North American and Midwinter champion in his class. He is a graduate of St. Mary’s College of Maryland, where he was a three time ICSA All-American.
Following his collegiate career, Healy was very successful on the national scene. He was a member of the US Sailing Team in 1994 and was the U.S. Sailing Men’s National Champion in 1995. He won numerous Mid-winter titles in Interclub dinghies. In 2002, he was the North American Lightning Champion and a year later he was the runner-up. He also found success in larger boats winning the Block Island Race Week two years in a row on his family’s 28-foot PHRF boat Sir-Prize.
Healy began his coaching career as an assistant coach at St Mary’s. During his time at St Mary’s, they won several district and national championships. He then became the head dinghy coach at the U.S. Coast Guard Academy for four years. He turned a struggling team into a nationally ranked one with five All-Americans. Healy also coached at the 1999 Youth Worlds in South Africa.