Jackson is a native of Milwaukee, Wisconsin, and attended Alexander Hamilton High School. He was an All-City Conference player and received all-state honors his senior year of high school. Prior to attending Central State University, Jackson played one season at the University of Wisconsin-Milwaukee (NCAA Division I).

In his first season, Jackson guide the Tigers to their first SWAC Regular Season Championship in nearly 30 years (1988-1989). During the regular season, Grambling State enjoyed the nation spotlight as being one of the teams in NCAA Division I with the longest winning streak, which got as high as 11 games before a loss to Arkansas-Pine Bluff. Jackson, which saw the team finish at 17-14 overall and 13-5 in SWAC play, earned several accolades, including SWAC Coach of the Year, NABC District 23 Coach of the Year and the Ben Jobe National Coach of the Year honor.