John Brown's raid was something of a dress rehearsal for major actors in the coming drama that would be the Civil War. Using hind-sight, historians have noted the coincidences that seemingly abounded among the players in the Harpers Ferry tragedy.
Brown had run into United States soldiers -later Civil War generals -Edwin V. Sumner (Union) and J.E.B. Stuart (Confederate) during the Bleeding Kansas years. Brown could not have known back in Kansas that Stuart would be the one that would come to the door of the fire engine house in Harpers Ferry to demand his surrender.
Colonel Robert E. Lee would be sent to Harpers Ferry while on leave at his Arlington home to supervise the counter-insurgency operations. Lee, of course, would reach the peak of Confederate command during the war and became the South's most famous general. Thomas Jonathan "soon to be Stonewall" Jackson was in charge of a group of Virginia Military Institute cadets that provided security at Brown's execution by request of Governor Henry A. Wise. In the groups of militia at Brown's hanging was an actor that would later achieve a notoriety that he would never see by his reputation on the stage. John Wilkes Booth might actually have taken a lesson from Brown's book when he used a terrorist action in his assassination of Lincoln in 1865. Henry Clay Pate, who would become a colonel of a cavalry regiment under J.E.B. Stuart during the war, visited Brown while in jail. Brown had captured Pate in Bleeding Kansas and had spared the Virginian's life.
Among the strangest of ironies was the fact that the first casualty of the Harpers Ferry raid (an action designed to help African Americans) was a free black man; railroad baggage handler Hayward Shepherd. Shepherd had inadvertently run into raiders Oliver Brown and Stewart Taylor as he looked for a co-worker during the initial chaos of the raid. When asked to stop on the railroad bridge, Shepherd walked back toward the railroad office, both men shot at him and hit Shepherd in the back. He would die the following day. In later years the United Daughters of the Confederacy and Sons of Confederate Veterans would dedicate a monument to Shepherd in Harpers Ferry for his "character and faithfulness." The monument is an interesting interpretative spin on what was probably nothing more than a man being in the wrong place at the wrong time.