Born in Powhatan County and raised within view of Jefferson’s Monticello, Mosby grew up on stories of Francis Marion, the “Swamp Fox” of the American Revolution, and studied military history, such as Napoleon’s Maxims . University of Virginia-trained, he was a small town Virginia lawyer opposed to secession when the War began in 1861. But when his state called for her patriotic sons to respond, he enlisted, joining the 1st Virginia Cavalry.
He showed extra-ordinary ability as a cavalry scout. By the end of 1862, the 29-year old Lt. Mosby had become General J.E.B. Stuart’s chief scout, and was detached from Stuart’s headquarters to operate behind enemy lines. Given the chance of a lifetime, he sought to prove a pet theory formed through years of studying military history. He believed that a minimal number of men staying at safe houses over a large rural area could launch devastating surprise cavalry attacks by day or night when a signal for a rendezvous was given. Attacks on outposts of the Union cavalry screen around Washington, guard stations, U.S. Military Railroad junctions, depots, trains, and supply wagon trains could not only weaken the morale of the enemy invader – fear is a powerful weapon – but tie up thousands of troops needed for operations against the main Confederate forces.