Nathan Bailey moved to Weymouth in 1978 and attended Weymouth South High School where he earned honors as a student and basketball player. He played three years as a starting forward and scored a school record 967 points.

His 40 points and 26 rebounds are both single game records. Nathan was named a Patriot Ledger All Scholastic in 1984 and 1985 and a Boston Globe Player of the Week in 1985. He was an Old Colony League All Star in his junior year and was selected the MVP of the league as a senior.

After high school Nathan attended the United States Naval Academy and was a starting forward on the nation's 8th ranked team that featured David Robinson. The team made it to the final eight in the NCAA Tournament.

He transferred to the University of Pittsburgh in his sophomore year where he continued his basketball career as a member of the nation's 4th ranked team. At Pittsburgh he was named to the Big East All Academic Team and the Athletic Directors' Honor Roll.

Nathan met his wife Linda, a student and Division One volleyball player at Pittsburgh University. He is a graduate of the Pittsburgh Law School and is a practicing attorney. Nathan and Linda live in Pittsburgh and have a 6 month old son, Evan.