He averaged 24.2 points, 8.1 assists and 5.0 steals per game as a senior to help Creswell win the 2000 Oregon State Basketball Championship (Class AAA).

Jackson continued his on court success with a storied four-season career at the University of Oregon, leading the Ducks to an Elite Eight finish in 2002 NCAA tournament as a sophomore.

He is second all-time in points scored, third in total steals, fourth in assists and seventh in rebounds and is first in free throws made.

In one of the greatest individual performances of all-time at Mac Court, Jackson scored 40 points — including 29 straight in the second half and overtime — as Oregon overcame an 18-point deficit to defeat Colorado 77–72 in the first round of the National Invitation Tournament on March 17, 2004.

He also became only the second freshman in Pac-10 history to record a triple-double when on February 17, 2001, he added 14 points, 11 rebounds and ten assists in a contest versus Washington.

Jackson averaged 12.5 points, 2.3 rebounds and 3.2 assists in 30.8 minutes in six games with Idaho, gaining the attention of the injury rattled Los Angeles Clippers.

[5] On April 18, 2007, in Toronto's last game of the regular season, Jackson exploded for a career-high 30 points and 5 assists while logging a career maximum 39 minutes in a defeat to the Philadelphia 76ers.

In his first game with that club (the only one that season), he scored 30 points in 31 minutes with 7–14 shooting, including 11–11 at the free throw line and 5–6 from long range.

[13] On February 20, 2013, Jackson was introduced as the new head coach at Northwest Christian University, in Eugene, Oregon, replacing Corey Anderson.

[14] During his first season at the helm of the Beacons, Jackson led his team to their first ever appearance in the NAIA Division II National Championship Tournament.