Kent Massey grew up in Oklahoma where he was a top athlete in high school. He played football and basketball and ran track. Massey was a three-time state champion in the 2-mile run on the track team. Massey went to college at the University of Oklahoma but finished his degree at Dominican College in San Rafael, California. He later went back to school and earned an MBA from Georgetown University in 1989.
Massey won a bronze medal in Soling Class at the 1996 Atlanta Olympics, sailing alongside Jim Barton and Jeff Madrigali. Massey / Barton / Madrigali came into Atlanta on a roll, having racked up multiple victories in the previous year. They won the Soling Pacific Coast Championship in October 1995, and then within the week won the Soling North America Championship. Shortly afterward they took the Soling Match Racing Championship. Massey was a member of the St. Francis and San Francisco Yacht Clubs. Massey and Barton also won a bronze medal at the 1994 Soling World Championships.