Jackson, 28, joined the Patriots as an undrafted free agent in 2018. He worked his way up to become a Pro Bowl player in 2021, leading the NFL with 23 passes defended that year. In his first four seasons in Foxborough, Jackson recorded 25 interceptions.
In 2022, Jackson tested free agency and signed a five-year, $82.5 million deal with the Chargers to join a defense that included Joey Bosa and Derwin James. It didn’t work out, however, as Jackson dealt with an early-season injury and was benched in Week 6. A patellar tendon tear suffered the next week officially ended his first season in L.A. early.
The 2023 season for Jackson started in a similar way to 2022. He started in the Chargers’ first two games and recorded an interception. However, Jackson was benched the following week and told NFL Network’s Bridget Condon that he was “confused” by the team’s decision.
The following week, the Patriots traded for the veteran CB, also swapping 2025 sixth and seventh-round picks with the Chargers. Though he saw some significant playing time at first, reliability questions emerged by Week 10, and he was eventually placed on the non-football illness reserve list, effectively ending his tenure with the Pats.