Bennett graduated from Walla Walla High School in 1983, playing football for his father, Shorty Bennett, and then embarked on a college football career at both the University of Idaho and Whitworth College. A 1988 graduate of Whitworth with a degree in secondary education and math, Bennett spent two years as a graduate assistant coach at Washington State University, adding a Master’s degree in physical education from WSU in 1990. He also spent one season as the offensive coordinator at California State University, Chico (Chico State) and one year as wide receivers coach at Idaho.
As a collegiate head coach, Bennett spent six seasons as the head coach at Western Oregon University in Monmouth, Ore., compiling a 27-32 record from 1995-2000. During that time, he helped guide the school through a transition from the NAIA to NCAA Div. II ranks, leading the Wolves to the NAIA playoffs and a Columbia Football Association championship in 1997.
Following his coaching stint at WOU, which also included three seasons as an assistant coach, Bennett spent six years at the NCAA Div. I level as an assistant coach. He was the quarterbacks coach and recruiting coordinator under Joe Tiller at Purdue University from 2001-05 before becoming the assistant head coach at Michigan State University under John L. Smith in 2006. While at Purdue, he coached current Dallas Cowboys quarterback Kyle Orton.
Bennett has been married to wife Melissa for 24 years. The couple has three children, sons Blaine John (22) and Matthew (19), and daughter Brianne (21).