He played two years of college basketball for Cleveland State University, where he made a notable game-winning full-court shot against Syracuse[1] and helped the Vikings past Wake Forest in the first round of the 2009 NCAA Tournament.

[2] As a pro, Jackson made a name for himself playing for the New Zealand Breakers in the Australian National Basketball League (NBL).

He was crowned the NBL's Most Valuable Player in 2013, garnered Grand Final MVP honors in 2013 and 2015, and was named to the All-NBL First Team in 2012, 2013 and 2015.

[4][5] Jackson subsequently enrolled at Northern Burlington County Regional High School in Columbus, New Jersey.

[7] After sitting out the 2006–07 season due to NCAA transfer regulations, Jackson starred at Cleveland State, helping them make two straight postseason appearances in 2008 and 2009.

[9] Between January and April, Jackson had multiple stints in the NBA with the Cleveland Cavaliers, San Antonio Spurs and Washington Wizards.

[17][18] He helped the Breakers win the minor premiership with a 21–7 record before guiding them to the NBL Grand Final, where they defeated the Perth Wildcats 2–1.

[22] After playing for the San Antonio Spurs during the 2012 NBA Summer League,[23] Jackson re-signed with the Breakers for the 2012–13 NBL season in August.

[27] The Breakers were minor premiers once again with a 24–4 record before returning to the NBL Grand Final, where Jackson won his second championship with a 2–0 defeat of the Wildcats.

[41] For the third time in three seasons, Jackson earned All-NBL first team honors and led the league in assists (6.0) per game.

[45][46] On October 11, 2015, in his 99th NBL game, Jackson recorded his fourth career triple-double with 14 points, 10 rebounds and a career-high 14 assists in the Breakers' 89–81 win over the Townsville Crocodiles.

[52] He responded to his poor form in the team's first game of February, recording a season-high 31 points, 10 rebounds and six assists in a 106–84 win over the Adelaide 36ers, keeping the Breakers' playoff chances alive.

Following the NBL season, Jackson had a six-game stint in Puerto Rico with Atléticos de San Germán.

[60][61][62] He made his debut for United in their season opener on October 7, recording 14 points, 13 rebounds and six assists in a 76–71 loss to the Breakers in Auckland.