If John Brown's raid on Harper's Ferry is considered the first battle of the American Civil War, Haywood Shepherd would be the first casualty of the war.

According to some documentation, John Brown's raid was intended to provide arms and ammunition for Brown to set up a stronghold in the mountains of Virginia where escaped slaves could find sanctuary. If this is considered to be true, then the death of Haywood Shepherd borders on irony.

Shepherd was a former slave who was stationed at Harper's Ferry and serving as station master when the attack came. A bullet from one of John Brown's men struck and killed Shepherd early in the attack. Taking all this into consideration, this means that John Brown, whose cause was freeing all slaves, killed a freed slave in an effort to gain the means to free more slaves.