Coach Chupp attended Lakewood Ranch High School and played four consecutive years for the junior varsity and varsity baseball teams. After his high school career Chupp continued to play baseball for the South Carolina Upstate division 1 college baseball team. Following that year, Chupp transferred to the State College of Florida where he played for one year and then finished his career at Valdosta State University in Georgia.
“Following my baseball career, I wanted to start coaching and helping kids in the Lakewood Ranch community. I started right away with the help of Coach Kennedy providing me the opportunity of becoming an assistant my first year, then allowing me to be head junior varsity coach the following two years,” stated Chupp.
“The key is not the will to win. Everybody has that. It is the will to prepare to win that is imprortant.”- Bobby Knight