Jackson was part of the famed University of Michigan Wolverines Fab Five along with former NBA players Chris Webber, Jimmy King, Jalen Rose, and Juwan Howard that reached the 1992 & 1993 NCAA Men's Division I Basketball Championship games as both Freshmen and Sophomores.

Although the Fab Five final four appearances have been forfeited,[2] he was not among the players called before the grand jury (Robert Traylor, Webber, Rose, Maurice Taylor and Louis Bullock)[3] in the University of Michigan basketball scandal and was not found to have received large amounts of money.

He was drafted in the Continental Basketball Association (CBA) by the Grand Rapids Hoops #35 in the 3rd round in 1995.

In a February 10, 2007 article on Yahoo Sports, Jackson says that: "It took me a long time to get over the fact that I was the only one that didn't make it to the NBA from the Fab Five, but I'm over it because I'm back home and I'm happy with what I'm doing with my life."

Jackson lives in Austin, Texas, where he runs a moving company and Rise Up, a not-for-profit organization that assists children socially, educationally and on the basketball court.