[1] Initially a student and football player at Springbrook High School in White Oak, Maryland, Jackson transferred to Dr. Henry A.

[3] As a senior in 2018, Jackson made 39 receptions for 612 yards and 12 touchdowns, playing both wide receiver and defensive back on a Wise team that went undefeated en route to the MPSSAA Maryland 4A state championship.

[8] Although he had been recruited as a wide receiver, Jackson was more interested in playing cornerback, and he convinced the Fort Scott Greyhounds coaching staff to let him change positions partway through the season.

[9] A coaching change at Fort Scott prompted Jackson to transfer to East Mississippi Community College to solidify an NCAA Division I opportunity.

[6][10] When the 2020 football season was canceled due to the effects of the COVID-19 pandemic, East Mississippi head coach Buddy Stephens connected Jackson to Freddie Roach and Nick Saban.

[6] After receiving offers from programs such as Oklahoma, Florida, Tennessee, and Auburn, Jackson committed to the Alabama Crimson Tide in August 2020 and signed with them that December.

[11][12] He made his Alabama debut on September 4, playing defensive back and taking a special teams role in the Crimson Tide's season-opening 44–13 victory over Miami.

[13][14] Used mostly on special teams, Jackson made his first start for Alabama in the 2022 College Football Playoff National Championship against Georgia, following injuries to Josh Jobe and Jalyn Armour-Davis.

[25] Jackson started all 12 games for the Ducks during the 2023 season, allowing only 19 receptions for 200 yards while recording 34 tackles, two quarterback sacks, and a team-leading three interceptions.

[36] Although the Vikings had an established cornerback group in Byron Murphy, Shaquill Griffin, and Mekhi Blackmon, they were in search of another young player to develop at the position.

[38] Jackson was the front passenger in a Dodge Charger headed north on Maryland Route 4 when it was struck by Cori Clingman, a 24-year old woman from Upper Marlboro, who was driving an Infiniti Q50 and changing lanes at high speed.