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.[1] He was rated as the No. 3 linebacker in Florida by the Florida Times-Union, and selected FSU over Auburn and West Virginia.
An All-Conference linebacker leading the Seminoles in tackles as a senior, Jennings was regarded as an NFL Draft prospect,[2][3] until just three weeks before the 2002 NFL draft, on March 30, 2002, he was near-fatally shot twice in the right shoulder by a jittery carjacker.[4] He eventually went undrafted and never played in the NFL.[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. Jennings claimed it was pre-Halloween prank.[6]
Jennings now holds the linebacker coaching spot at Sandalwood High School where his son Branden attends.