Following a standout career, where he led the state of Nevada in assists as a senior, he went to the College of Southern Idaho (CSI).

He averaged 18.6 points and 4.4 assists per game in 2010–11 and was named a first-team All-American and the NJCAA Player of the Year at the conclusion of the season.

Jackson was named second team All-Big 12 Conference and an honorable mention All-American by the Associated Press.

On April 4, 2013, Jackson ended his college career with a championship win over Iowa at the National Invitation Tournament (NIT).

On July 12, 2013, his draft rights were traded, along with Jrue Holiday, to the New Orleans Pelicans in exchange for Nerlens Noel.

[23][24] Despite the injury, he signed a one-year, partially guaranteed contract with the 76ers on July 24, 2014,[25] only to be waived on September 30 after he was ruled out for six to 12 months.

[29] He made his season debut for the Stampede three days later in a 98–92 win over the Fort Wayne Mad Ants, recording six points, one rebound, two assists and one steal in 11 minutes of action off the bench.

[36] That night, he made his NBA debut in a 123–107 loss to the Houston Rockets, recording seven points, one rebound and two assists in 11 minutes off the bench.

[45] On July 14, 2017, Jackson signed a one-year deal, with an option for another season, with Maccabi Tel Aviv of the Israeli Premier League and the EuroLeague.

[46] In his first Euroleague game for Maccabi, Jackson starred with 27 points, 9 assists and 7 rebounds in an 88–71 win over Brose Bamberg.

[citation needed] On July 4, 2018, Jackson signed with the Beijing Fly Dragons of the Chinese Basketball Association.

[53] On August 9, 2020, Jackson officially signed a one-year contract with Panathinaikos of the Greek Basket League and the EuroLeague.

[54] On September 23, 2020, he played in the semi-final of the Greek Basketball Super Cup,[55] he was injured and left the team on October 13.

[59] On January 22, 2022, Jackson signed with HDI Sigorta Afyon Belediye of the Basketbol Süper Ligi (BSL).

[60] On February 22, 2024, Jackson was announced by Libyan club Al Ahly Ly of the Basketball Africa League (BAL).