Phill Dearstyne began swimming in the summer for the Westwood Swimming and Tennis Association at the age of 5 where he competed until the age of seventeen when he won the Westchester County Championship in the 100 freestyle and the high point award for the meet. Phill was also a USA swimmer during the winters for the Aqua Kings from his early years through high school where he achieved junior national status in the 50 freestyle.
During his high school career, Phill swam for Iona Prep, winning the Tom Borras award for high achievement in high school swimming as well as the Con Ed sports award. He was Captain of the New Paltz Hawks Swimming and Diving Team through college and has been coaching the Harrison Varsity Girls (fall season) and Boys (winter season) for the last twenty years at Harrison High School where he also teaches English. He also returned to Westwood Swimming and Tennis where he was the assistant pool director for Bill Mentz for ten years before taking over the head coaching position for the Dolphins for eleven seasons.
Phill joined the staff of Club Fit Aquatics in 2015, first working as an assistant coach to Marc Quintiliani before implementing a triathlete training course in the spring of 2018. Recently, Phill competed in the Westchester Triathlon in the fall of 2018 and continues to coach at Club Fit of Briarcliff, as well as coach and teach at Harrison High School.