Career
At Benjamin Franklin High School, Jennings played football, basketball and ran the 200 meters and participated in the shot-put. The 30-year-old father of 4-year-old Mason, Jennings played basketball at North Philly rec centers for years before he decided to box at the age of 24. Jennings was 13-4 as an amateur.
He reached the finals of the 2009 National Golden Gloves, losing by decision to veteran Lenroy Thompson.
In 2012, Bryant earned a 10-round unanimous decision over fellow prospect Maurice Byarm (13-0-1), of Washington, District of Columbia, on January 21 at the Asylum Arena in South Philadelphia on the National Broadcasting Company Sports Network Fight Night opening card.
Neither fighter had gone beyond six rounds before the bout, he took the bout on five days" notice. The fight took place at Aviator Sports Complex, Brooklyn, New York and was televised on National Broadcasting Company Sports.
Jennings controlled the fight with his jab and power punches.
Jennings then faced Steve Collins (25-1) on June 16, 2012 at the Prudential Center, Newark, New Jersey. The fight was co-main event as part of National Broadcasting Company Sports Fight Night event, including Tomasz Adamek versus Eddie Chambers. The fight took place at the Prudential Center, Newark, New Jersey.
Jennings faced Bowie Topou on December 9, 2012 at McGonigle Hall, Philadelphia, Pennsylvania.
The fight was aired on National Broadcasting Company Sports Fight Night. He beat high-rank contender Mike Perez to earn title shot as mandatory challenger, Number.1 WBC contender.
Jennings signed with promoters Gary Shaw and Antonio Leonard after buying out his existing agreement with Russell Peltz. Jennings versus Klitschko
After the fight, Klitschko admitted that this was one of his hardest fights in years.
Jennings versus Ortiz
Jennings lost by TKO to undefeated Cuban boxer and heavyweight contender Luis Ortiz on December 19, 2015.