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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.

William A Jackson was a coachman for the family of Jefferson Davis for only a few months. According to an article in Harper's Weekly, dated June 7, 1862, Jackson fled to Union lines outside Fredericksburg, leaving behind his wife and three children. Harper's summarizes a letter written to the Secretary War by General McDowell giving instances of information Jackson provided Union officers. He provided some information he'd gleaned from overhearing conversations with some of President Davis' confidants, but most of the information he passed along, which seemed of greatest interest to his hearers, had to do with his understanding of the personal opinions of Davis, his family and close advisers having to do with their fears for the future of the Confederacy. Claims have been made in recent times that Jackson's recollections could be specially relied upon because slaves, unable to read, depend much more on memory. Ironically, the Harper's article, evidently unread by some who've made these claims for Jackson, makes a point of saying not only that Jackson was remarkably intelligent, but also that he read and wrote quite well.

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