James C. Dragon has always been a sports fan, especially baseball. Dragon has played on amateur baseball teams in Lowell for numerous years, in addition to being a part-owner of the New Bedford Bay Sox. He also coached young basketball teams in Tewksbury, as well as founding and coaching Tewksbury's first American Legion baseball club, which made the playoffs by year two.

James C. Dragon graduated from Lynn Classical High School in 1971, where he participated in varsity basketball and golf. In 1983, he received a bachelor's degree from the University of New Hampshire and a law degree from the New England School of Law.