Jennings won the 1991 Frances Pomeroy Naismith Award, given to the outstanding collegiate senior six feet tall and under, and was a second-team consensus All-American.

In that game, Jennings made 8 of 10 field goals, including 3 of 4 three-pointers, and was perfect in 4 free-throw attempts in 41 minutes.

From 2004 to 2007, Jennings was the head coach of the boys' varsity basketball team at the private Highland School in Warrenton, Virginia.

[2] Jennings joined the staff at his alma mater, East Tennessee State, as a graduate assistant coach for the 2007–08 season while he completed his degree.

[7] On July 27, 2023, Jennings was named head coach at Culpeper County High School, his alma mater.