He played college football for the Maryland Terrapins and signed with the New England Patriots as an undrafted free agent in 2018.

[2] Jackson began his college career with the Florida Gators but injured his shoulder in the opening game and did not play for the rest of the season.

[5] While Jackson was a student at Riverside, college teams including the Michigan Wolverines and Penn State Nittany Lions expressed an interest in recruiting him.

[19] Jackson helped the Patriots reach Super Bowl LIII, where they defeated the Los Angeles Rams 13–3.

In week 4 against the Buffalo Bills, Jackson intercepted quarterback Josh Allen twice and blocked a punt which was recovered by teammate Matthew Slater for a touchdown in the 16–10 win.

[22] In week 14 against the Kansas City Chiefs, Jackson recorded his third interception of the season off a pass thrown by Patrick Mahomes during the 23–16 loss.

[21] In Week 1 playing in a game against the Miami Dolphins, Jackson recorded his first interception of the season off a pass thrown by Ryan Fitzpatrick late in the fourth quarter to secure a 21–11 Patriots' win.

[26] In Week 7 against the San Francisco 49ers, Jackson recorded another interception, this time off a pass thrown by Jimmy Garoppolo, during the 33–6 loss.

[32] On March 17, 2021, Jackson received a second-round restricted free agent tender worth $3.384 million from the Patriots.

[38][39] In August, he underwent ankle surgery, which forced him to miss the preseason and the season opener against the Las Vegas Raiders.

[41] Jackson struggled while playing for the Chargers, leading to him being benched for Michael Davis in the Week 6 Monday Night Football matchup with the Broncos.

The warrant was a result of Jackson not appearing in court for a probation violation hearing, which stemmed from a criminal speeding arrest in 2021.