Mike was named the Connecticut Gatorade Player of the Year his senior year at Rockville High School before attending the University of Connecticut. At UConn, Leonard played under legendary coach Andy Baylock for four seasons. Mike signed as a free agent with the Boston Red Sox, where he finished the 2006 season with Single A Greenville. During the offseason, Mike instructs at several of the Academy's camps, specializing in hitting and catching. He is currently the head coach at Middlebury College.