Jackson was undrafted in 1999 following a college career at the University of Detroit Mercy and began his professional career with the Detroit Pistons (1999-00), going on to play for the Toronto Raptors (2002–03), Atlanta Hawks (2003) and New York Knicks (2005), averaging 2.2 points, 1.1 rebounds and 1.5 assists per game in his NBA career. The Knicks included Jackson in a trade along with Mike Sweetney and Tim Thomas in exchange for Antonio Davis and Eddy Curry of the Chicago Bulls. He was cut by the Bulls on October 18, 2005, and was signed by the Milwaukee Bucks on December 15, 2005. He played for the Bucks in the 2005-06 season, with the team renouncing their NBA rights to him on July 19, 2007. Jackson signed with the Seattle SuperSonics on October 1, and was waived during that month.