Career
He played college baseball at the University of Miami and previously played in Major League Baseball (MLB) for the Saint Louis Cardinals and Los Angeles Angels of Anaheim. Jackson played amateur baseball for Westminster Academy, Gulliver Preparatory, and Florida Christian School before being drafted by the Saint Louis Cardinals in the fifth round of the 2009 Major League Baseball Draft out of the University of Miami. 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.
He was 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. He had two hits in 17 at-bats that year and was hitless in seven at-bats the next season.
He spent most of both seasons in American Automobile Association with the Memphis Redbirds. Jackson was claimed off waivers by the Astros on November 20, 2013.
A month later, on December 18, 2013, he was traded to the San Diego Padres in exchange for Jesús Guzmán.
He played in only 11 games in 2013, split between the Arizona League Padres and the American Automobile Association El Paso Chihuahuas as a result of wrist surgery. He was claimed off waivers by the Los Angeles Dodgers on November 3, 2014 and then designated for assignment by the Dodgers on November 24. Jackson was traded to the Los Angeles Angels of Anaheim for Drew Butera on May 7, 2015.
Jackson signed a minor league deal with the Philadelphia Phillies in November 2015.