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Jefferson Davis' personal coachman during most of the American Civil War, Jackson was representative of the Confederacy's underestimation of their African American (Negroes in the language of the time) slave population.

Playing the part of the obedient and faithful slave, smiling as he carried out his duties as coachman, Jackson would listen in as Jefferson Davis held meetings or conferred with military aides. He would then make his way through the Confederate lines unharrassed, as he was always "on business for master" and steal his way through Union lines to relay the information to the Union high command. Throughout all his adventures, neither Jefferson Davis nor any of his ranking associates suspected the betrayal.

Jackson would become renown as one of the most amazing of a group of slaves and former slaves to work for the Union cause. They were known as "intelligent contraband" to the Union, a name which reflected the concept of slaves as goods, making their movement across enemy lines theoretically an act of smuggling.