Gary Boles began his Kaskaskia College basketball career playing for Coach Chuck Mundell. Gary was a member of the 1960-61 Blue Devils Basketball team which finished 19-8. Gary had a career high of 48 points in one game that season, assisting his achievement of 28 points per game in scoring, resulting in Gary's ranking of 8th in the nation. This accomplishment was subsequent to his receiving NJCAA All-American Honors and being named All Conference Team Most Valuable Player for the Southern Illinois College Conference. 

Gary also played in the North-South All-American Game in Lawton, Oklahoma under the direction of Coach Jack Hartman. After Kaskaskia College, Gary continued his education on a basketball scholarship at McKendree College and after completing college, Gary taught and coached for sixteen years. Gary was a basketball coach at Odin Grade School where he won a SIJHAA State Title in 1970 with a 26-1 record.