Jennings was born in Murfreesboro, Tennessee, and at a young age his family moved to Dayton, Ohio.
He starred at Dayton's Wilbur Wright High School where he was selected to play in the Ohio North/South All-Star game.
As a junior, he averaged 17.6 points and 16.1 rebounds and finished second in the OVC Player of the Year balloting to Morehead State's Harold Sergent.
[2] In his senior season, Jennings led the Racers to a 16–9 record and averaged 19.6 points and 15.1 rebounds.
[3] The Racers went to the program's first NCAA Tournament that year, losing to defending champion Loyola 101–91.