The Seattle Mariners selected Jackson in the fifth round of the 2015 Major League Baseball (MLB) draft.

[2] The Seattle Mariners selected Jackson in the fifth round of the 2015 Major League Baseball (MLB) draft.

[9] On March 1, 2017, the Mariners traded Jackson and Aneurys Zabala to the Los Angeles Dodgers for Chase De Jong.

[10] The Dodgers assigned him to the Rancho Cucamonga Quakes of the California League,[11] where he played in 66 games, batting .254/.367/.429 with eight home runs and 30 RBIs before his promotion to the Tulsa Drillers of the Class AA Texas League, where he finished the season, hitting .234/.346/.324 with one home run and ten RBIs in 29 games.

[15] The Philadelphia Phillies selected Jackson in the Rule 5 Draft on December 13, 2018, and traded him that day to the Baltimore Orioles in exchange for international bonus slot money.

[20] He spent the rest of the 2019 season with the Triple-A Oklahoma City Dodgers, hitting .209/.300/.319 with 6 home runs and 28 RBIs.

[22] On December 10, 2020, the New York Mets selected Jackson in the minor league portion of the 2020 Rule 5 Draft.

On April 15, 2022, Jackson was added to the Athletics roster for their road trip to Toronto as a coronavirus-related substitute.

[31] His older brother, Brett Jackson, played in Major League Baseball as an outfielder for the Chicago Cubs and Arizona Diamondbacks.