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Jackson is a product of the New York Red Bull Academy, which he joined at the age of 13. At age 16, he moved to France with his family and played with Toulouse FC for two seasons, becoming the first American to sign with the team. He played with amateur team Crossfire FC when he returned to the U.S. from 2019-2020 and trained with Seattle Sounders in 2020. 

In April 2021, Jackson signed with Minnesota United FC (MNUFC) as a Homegrown Player after Minnesota traded for his rights from the Red Bulls. Jackson spent the 2021 season on loan to North Carolina FC before playing with MNUFC2 on a season-long loan in 2022. His performances for MNUFC2 stood out among the best of the league, particularly in key passes / chances created. The Loons midfielder was the top player in that category with 70 scoring chances created. At the club level, Jackson led MNUFC2 in games played (23 GP, 21 GS), goals scored (10) and assists provided (seven). The midfielder additionally finished tied for third in MLS NEXT Pro regular-season action with his seven assists. Among his key contributions on the field, Jackson scored MLS NEXT Pro’s 800th-ever goal during MNUFC2’s match at Timbers2 on September 11. 

Jackson’s performances throughout the 2022 season earned him MLS NEXT Pro Best XI honors.