He played college football for the Evansville Purple Aces, Illinois Fighting Illini and Northwestern Wildcats.

Since he was a senior after his single season at Northwestern, he elected to enter the NFL draft and surprised many by being selected by the New York Giants in the fourth round.

After his failed stints in New York he played for the CFL's Ottawa Renegades and Toronto Argonauts; and the Evansville BlueCats of the Indoor Football League.

[2] Following his senior season in high school, Bennett accepted a baseball and football scholarship at the University of Illinois.

[2] However, after his junior season the school decided to drop football forcing Bennett to transfer to Northwestern University.

[2] On March 10, 1999, when some National Football League (NFL) scouts came to work out D'Wayne Bates and Barry Gardner, Bennett decided to join the workout.

In 2001, New York expected Bennett to work in tandem with Tiki Barber but after suffering a hamstring injury, he was released on September 3, 2001.

[5] After multiple injuries to their running backs, the Giants became interested in re-signing Bennett but because of NFL rules they were unable to do so until January 2002.

During this time period, he was offered contracts by the Philadelphia Eagles and Miami Dolphins but rejected both hoping to return to the Giants.