Jackson attended Neumann-Goretti High School, where he played with future Syracuse teammate Scoop Jardine.

That season, Jackson averaged 15 points per game and was named AP All-State Class AAAA second team.

[4] Jackson would join the starting lineup in his sophomore season against Memphis on December 20, 2008, scoring 14 points to go along with seven rebounds.

Jackson finished the season leading the league in rebounds, field goal percentage and blocked shots.

[13] On January 27, 2013, in a game against the Rio Grande Valley Vipers, Jackson recorded a career high of 25 rebounds to go along with 21 points in a 106–91 win.

[17] On January 19, 2015, he signed with Rain or Shine Elasto Painters at the Philippines playing as import,[18] replacing Kenny Adeleke due to problems in travel documents.

[20] On October 31, 2015, Jackson was selected by the Iowa Energy with the ninth overall pick in the 2015 NBA Development League Draft.

[21] On November 14, he made his debut for Iowa in a 98–95 win over the Sioux Falls Skyforce, recording ten points, three rebounds, one assist and two blocks in 29 minutes.

[23] Four days later, he made his debut for Delaware in a 125–109 win over Raptors 905, recording 13 points, seven rebounds, one assist and one block in 23 minutes off the bench.

[27] On May 21, 2023, Jackson signed with Satria Muda Pertamina of the Indonesian Basketball League to replace Allen West's position in the team.

In five games, he averaged 7.4 points and 7.4 rebounds to help lead Boeheim's Army to the Semifinal Round where they fell 81–77 to the eventual champions Overseas Elite.