After signing, Jackson spent his first professional season with the AZL Mariners, slashing .280/.344/.476 with two home runs, 16 RBIs, and six doubles in 23 games. He began the 2015 season with the Clinton LumberKings, where he struggled, batting .157 with no home runs and 35 strikeouts in 28 games. The Mariners returned Jackson to extended spring training in May, and reassigned him to the Everett AquaSox when their season began in June.[13] He spent the remainder of 2015 with Everett, batting .239 with eight home runs and 25 RBIs in 48 games. Jackson spent 2016 with Clinton where he batted .243 with 11 home runs and 55 RBIs in 92 games.
Atlanta Braves
On November 28, 2016, the Mariners traded Jackson and Tyler Pike to the Atlanta Braves for Rob Whalen and Max Povse.[14][15] Jackson began the 2017 season with the Florida Fire Frogs, and later that season, was promoted to the Mississippi Braves. He hit .267/.328/.480 with 19 home runs and 65 RBIs in 96 games[16] between the two clubs.[17]
The Braves added Jackson to their 40-man roster after the 2018 season.[18] They promoted him to the major leagues on April 7, 2019,[19][20] and he made his major league debut that afternoon. In 2020 for Atlanta, Jackson only received seven at bats, but recorded his first two major league hits.[21]
On June 24, 2021, Jackson was placed on the 60-day injured list with a strained left hamstring.[22] Jackson was reinstated from the injured list on July 21.[23]
On April 6, 2022, Jackson was traded to the Milwaukee Brewers in exchange for Hayden Cantrelle and Alexis Ramirez.[25] Jackson went 3–for–12 (.250) in 5 games for the Brewers, spending the majority of his time in Triple–A with the Nashville Sounds. His season ended prematurely when he was placed on the injured list on August 27 with left wrist inflammation.[26] On December 2, he was removed from the 40-man roster and sent outright to Triple–A Nashville.[27]
Tampa Bay Rays
On August 1, 2023, Jackson was traded to the Tampa Bay Rays in exchange for pitcher Evan McKendry.[28] In 14 games for the Triple–A Durham Bulls, he batted .281/.305/.561 with four home runs and ten RBI. Jackson elected free agency following the season on November 7.[29]
Jackson re–signed with the Rays organization on a minor league contract for the following day. He began the 2024 season back with Durham, and hit .282 with 7 home runs and 18 RBI in 22 games. On May 3, 2024, the Rays selected Jackson's contract, adding him to the major league roster.[30] In 58 games for Tampa Bay, he slashed .122/.201/.237 with three home runs and 12 RBI. On September 5, Jackson was designated for assignment by the Rays.[31] He cleared waivers and was sent outright to Durham on September 7.[32] Jackson elected free agency on October 1.[33]
New York Yankees
On November 8, 2024, Jackson signed a minor league contract with the Cincinnati Reds organization.[34] On December 20, the Reds traded Jackson and Fernando Cruz to the New York Yankees in exchange for Jose Trevino; he was subsequently added to New York's 40–man roster.[35]
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