 He lost bouts against future contenders Chris Byrd, Brian Nielsen, and Jeremy Williams.In 1998 he beat Alex Stewart, setting up a shot at a fringe belt in 1999 against Monte Barrett.Barrett won easily, and Jackson went on to lose to a "who's who" list of heavyweight contenders, including Fres Oquendo, Wladimir Klitschko, Larry Donald, Derrick Jefferson, and Dominick Guinn.