He was all three. Mosby and his men were rough and tough heroes to residents who felt protected by them and offered them places to stay, and to the South in general for their successful raids. Although officially volunteers in the military, as partisan rangers they were obligated to supply their own needs. They made good use of the plunder taken in frequent raids, including the finest horses and guns.
Uniforms weren’t a concern because Mosby told his men to wear any piece of gray clothing.
In a time when men still camped in large numbers and marched as a unit directly into enemy fire, Mosby’s methods were revolutionary. His headquarters were in the saddle; there was no place for the enemy to attack. His raids occurred when the time was right and no one knew his plans until they met at the appointed place.
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He modeled his operation on Continental Army Brig. Gen. Francis Marion, known as the Swamp Fox, who ambushed the British and then disappeared into South Carolina woodland or swamps during the American Revolution. Marion, in turn, had learned the technique from the Cherokees during the French and Indian War.
Mosby, a lawyer, joined the Confederate army when he was 28 and married with two children. He served under cavalry commander Capt. J.E.B. Stuart, a man his own age and one he came to idolize. He was Stuart’s scout on his famous 100-mile ride around Union Gen. George B. McClellan’s army in June 1862.
It was Stuart who acquiesced to Mosby’s request in December 1862 to give him a few men and allow him to try out his Swamp Fox-inspired plan to disrupt Union activity in Loudoun County. The men often met at Rectors Cross Roads, near Middleburg, at the start of a raid because of the easy access, friendly residents and good spring for watering the horses.
By late February, Mosby’s Raiders had scored three successful hits on Union outposts. In response, Union Col. Sir Percy Wyndham, stationed at Fairfax Court House, dispatched 200 troops under Maj. Joseph Gilmore on March 2 to find Mosby and arrest him. Gilmore headed to Middleburg, a town suspected of harboring the raiders, but en route the officer and his troops got drunk when several bottles were passed around. When they reached Middleburg, they tore up the town, searched every house and then arrested all the old men of Middleburg — the only men around — and took them as prisoners of war.