Growing up in Kingston, Jamaica, Osbourne lived primarily with his grandmother and then his great grandmother. His mother had him when she was 18 and still in school, and his father moved away to England when he was seven. At the age of 9, Osbourne moved to Flatbush section of Brooklyn, New York. He would bounce around after that, making a stop in Florida where he played high school football alongside Jacoby Brissett in William T. Dwyer High School.[2] After dropping football for wrestling, he exceled as a member of the school’s wrestling team, where he became a three time state finalist.[10] Osbourne enrolled at Wisconsin's Carroll University, where his high school coach Ben Tomes had just accepted a position. After reaching nationals as a freshman, Osbourne hit a bump in the road, as the wrestling program was shut down the ensuing year.[11][12]
Osbourne works as an assistant teacher for his full-time job.[13]
Mixed martial arts career
Early career
Osbourne made his amateur mixed martial arts debut in 2013, originally starting his training at small gym in Waukesha, Wisconsin. He made his mixed martial arts debut at NAFC: Explosion in 2015, he submitted Brent Lee via rear-naked choke in the second round, before defeating his next two opponents in David Rhodes and Doug Milbrath. He would then lose his first professional fight against Antonio Sanchez via unanimous decision at RFA 39, Osbourne faced Cory Galloway at Pure Fighting Championships 5, and went on to defeat him via split decision. Osbourne would lose against this time to Jose Luis Calvo via kneebar in the first minute of the bout at United Combat League: Havoc In Hammond 4. Osbourne would win his next three bouts; Seigenald Aurtan Daley Jr in the first round via triangle choke at Pure Fighting Championship 9, Daley Jr for the second time via TKO in round one at Pure FC 10, and finally Kelly Offield in round one via triangle choke at HD MMA 15.[14][15]
Dana White's Contender Series
Osbourne faced Armando Villarreal on July 16, 2019, at Dana White's Contender Series 20 for a chance at a UFC contract. He won the bout after submitting Villarreal via armbar in the first round, earning a UFC contract in the process.[16]
Ultimate Fighting Championship
Osbourne made his UFC debut against Brian Kelleher at UFC 246 on January 18, 2020.[17][18] He lost the fight via a submission in the first round.[19]
Osbourne was expected to face Jerome Rivera at a UFC event on January 30, 2021. The event never materialized and the pairing was canceled.[20]
Osbourne was expected to face Denys Bondar in a catchweight bout of 130 pounds on February 6, 2021, at UFC Fight Night: Overeem vs. Volkov.[21] However, Bondar withdrew during fight week due to undisclosed reasons and was replaced by Jerome Rivera, with their bout taking place at featherweight.[22][23] Osbourne won the fight via knockout out in round one.[24]
Osbourne was expected to face Amir Albazi on July 17, 2021, at UFC on ESPN: Makhachev vs. Moisés.[17] However, Albazi pulled out of the fight in late June citing injury. In turn, Osbourne was pulled from the card entirely and rescheduled for a future event.[18]
Osbourne faced Manel Kape on August 7, 2021, at UFC 265.[25] At the weigh-ins, Kape weighed in at 129 pounds, three pounds over the flyweight non-title fight limit. The bout proceeded at catchweight and Kape was fined 20% of his purse, which went to Osbourne.[26] He lost the fight via knockout in round one.[27]
Osbourne faced C.J. Vergara on November 6, 2021, at UFC 268.[28] At the weigh-ins, Vergara weighed in at 127.4 pounds, 1.4 pounds over the flyweight non-title fight limit. The bout proceeded at a catchweight and he forfeited 20% of his purse to Osbourne.[29] Osbourne won the fight via unanimous decision.[30]
Osbourne was scheduled to face Denys Bondar on February 25, 2023, at UFC Fight Night 220.[36] However, Bondar withdrew from the event for undisclosed reasons and he was replaced by Charles Johnson.[37] Osbourne won the fight via split decision.[38]
Osbourne next faced promotional newcomer Asu Almabayev at UFC on ESPN 50 on August 5, 2023.[39] He lost the fight via a rear-naked choke submission in the second round.[40]
Osbourne faced Jafel Filho on March 16, 2024, at UFC Fight Night 239.[41] He lost via rear-naked choke submission at the end of the first round.[42]
Osbourne faced Ronaldo Rodríguez on September 14, 2024 at UFC 306.[43] He lost the fight by unanimous decision.[44]
Osbourne is scheduled to face promotional newcomer Luis Gurule on April 5, 2025 at UFC Fight Night 256.[45]
