Jackson started training in wrestling at high school to get away from street life as most of his friends ended up in jail or dead. With good results in wrestling, Jackson set his goal to be an Olympic wrestler; however, he chose to stay back and take care of his sick grandparents and turned down the opportunity to wrestle in college. Jackson did an invitational wrestling match, Team USA vs. Team Japan and started training in the Olympic training center in Marquette, Michigan. His dream of becoming an Olympics wrestler would not materialize as in February 2013, International Olympic Committee members voted to remove wrestling from the Olympic programme. During this time, one of his friends, Devondrick Bankston, was preparing for a fight against Raufeon Stots, and asked him to help on wrestling drills at Red Schafer MMA gym. At the gym, he met Gato, a Puerto Rican, who managed to talk him into competing in a Brazilian jiu-jitsu tournament without a real class instructions. Eventually, Jackson gave up his Olympics dream and transitioned to mixed martial arts.
Jackson started his professional MMA career since 2017 and fought primarily on the regional circuit in the Pacific Northwest United States. He amassed a record of 6-0 before being signed by UFC.
Two month after the win over DiSciullo, Jackson made his promotional debut on 11 day notice, replacing Benito Lopez, on August 4, 2018 against Ricky Simon at UFC 227. He lost the fight by unanimous decision. Jackson was originally scheduled to face Brian Kelleher on November 3, 2018 at UFC 230, replacing injured Domingo Pilarte At the weigh-ins, Kelleher weight at 137 pounds, 1 pound over the bantamweight non-title fight limit of 136. He was fined 20 percent of his purse, which went to Jackson. On November 3, it was reported that Kelleher withdrew from the bout due to illness and thus the fight was cancelled. The pairing was left intact and rescheduled for December 29, 2018 at UFC 232. At the weigh-ins, Jackson weighed in at 137 lbs, 1 pound over the non-title fight bantamweight limit of 136 lbs. Jackson was fined 20 percent of his purse to Kelleher and the fight proceeded at catchweight. Jackson won the fight via submission in the first round. Jackson faced Andre Soukhamthath on April 13, 2019 at UFC 236. He won the fight by unanimous decision. Jackson faced Felipe Colares on January 25, 2020 at UFC Fight Night 166. He won the fight via unanimous decision. Jackson faced Brett Johns on July 19, 2020 at UFC Fight Night 172. He lost the fight via unanimous decision.
