A native of Miami, Jennings attended Carol City High School, where he was a first-team Class 6A linebacker as a senior.
Jennings led the Chiefs in tackles and had a dominating performance in the 1996 state championship win over Tampa Hillsborough.
[5] Jennings settled in Jacksonville, Florida, and became an assistant football coach at Mandarin High School.
In November 2009, he was charged with aggravated assault after a failed attempt to rob a Check 'n Go store in the Southside neighborhood of Jacksonville.
[6] Jennings now holds the linebacker coaching spot at Sandalwood High School where his son Branden attends.