 His best year as a pro came during his rookie season with the Cavaliers when he appeared in 55 games and averaged 6.1 points per game.After his professional playing career ended, Bennett served as an assistant coach under Rick Pitino at the University of Kentucky from 1995 to 1997 and, later, under Pitino, with the Boston Celtics, during the 1997–98 NBA season.In 1996, while an assistant at Kentucky, the Wildcats won the NCAA Championship, defeating Syracuse, 76–67.