[1][2] As a senior, Jackson averaged 25.9 points, 5.7 rebounds, 2.9 assists, and 2.6 steals per game, finishing as runner-up for the Indiana Mr. Basketball to Zak Irvin.

[4] His performances with Marian earned him a selection for the 2013 McDonald's All-American Boys Game, and he was the first Northern Indiana native to receive this honor since Shawn Kemp in 1988.

[4][5][6] Jackson finished the game with 5 points, 4 assists, and 2 steals and won the Jack Daly Sportmanship Award and the Skills Competition.

[11] Jackson commented on the situation, saying that although he had been apprehensive to play along a senior point guard, he realized that it would benefit his game.

[1][16] In his sophomore season, Jackson scored a career-high 22 points against Michigan State; this was the first meeting between the schools in 35 years.

[26] On November 6, he made his professional debut in a 123–107 loss to the Denver Nuggets, recording eight points, three rebound and two assists in 11 minutes off the bench.

[27] During his rookie season, he has received multiple assignments to the Maine Red Claws, the Celtics' D-League affiliate.

On January 14, 2018, Jackson was signed to a two-way contract with the Philadelphia 76ers and NBA G League affiliate the Delaware 87ers.

[36] On October 1, 2020, after averaging 13 points, 4.5 rebounds, and 8.5 assists per game, Jackson was named the Lithuanian League MVP of September.