Jackson played amateur baseball for Westminster Academy,[1] Gulliver Preparatory,[2] Florida Christian School,[3] and the University of Miami.

In 2010, Jackson split the year between the Single-A Quad Cities River Bandits and the High-A Palm Beach Cardinals, logging a .278/.359/.362 slash line with 3 home runs and 35 RBI.

The following season, Jackson played for the Double-A Springfield Cardinals, batting .278/.334/.415 with career-highs in home runs (11) and RBI (73).

Jackson was called up to the majors for the first time on August 10, 2012, and he made his debut the next day, as the starting second baseman against the Philadelphia Phillies,[9] going hitless in three at-bats.

His first MLB hit was a single to right field off Dallas Keuchel of the Houston Astros in a pinch-hit appearance on August 23.

[13][14] He played in only 11 games in 2013, split between the Arizona League Padres and the Triple-A El Paso Chihuahuas as a result of wrist surgery.

[25] Jackson was assigned to the Triple-A Lehigh Valley IronPigs to begin the 2016 season and hit .214/.347/.238 with no home runs and 7 RBI in 30 games.

[26] However, Jackson was released by the Angels on August 10 after posting a .262/.351/.306 slash line in 62 games with Triple-A Salt Lake.

[33] On January 22, 2018, Jackson signed with the Sugar Land Skeeters of the Atlantic League of Professional Baseball.

[37] On August 27, 2021, Jackson was traded to the Gastonia Honey Hunters of the Atlantic League of Professional Baseball for future considerations.