A native Rhode Islander, Coach Greenfield grew up around the water. He first started sailing locally on Narragansett Bay at Saunderstown Yacht Club and then attended Boston University where he sailed for eight seasons and served as a captain for the nationally-ranked coed team. In recent years, Greenfield has been an active member of the 5O5 class as well as various inshore and offshore keelboat classes. He has won the ORC East Coast Championships and NYYC Annual Regatta as the tactician on the Tripp 41 Entropy and placed first in division, and overall, in the PHRF class for the Vineyard Race as the navigator on the R/P45 Miracle. As a team racer, Greenfield has competed at a number of U.S. Racing Championships (Hinman Trophy) and British Team Racing Championships (Wilson Trophy) including two second place finishes at the Wilson Trophy. In 2015, Greenfield and his team earned a silver medal at the ISAF Team Racing World Championships.