In 2010, Jackson played for the Daytona Cubs of the Class-A Advanced Florida State League, and participated in the 2010 All-Star Futures Game.

Rated as the 38th best prospect in baseball by Baseball America before the 2011 season, Jackson started the year with the Tennessee Smokies of the Class-AA Southern League, before earning a promotion to the Iowa Cubs of the Class-AAA Pacific Coast League.

[7] On August 5, 2012, Jackson was called up by the Cubs and made his MLB debut, batting second, as their starting center fielder.

[9] On August 14, 2014, the Cubs traded Jackson to the Arizona Diamondbacks in exchange for right-handed pitcher Blake Cooper.

[citation needed] The San Francisco Giants selected Jackson from the Diamondbacks in the Class AAA phase of the 2014 Rule 5 draft.