Tough is also credited as being a pony express rider and some reports list him as engaging in horse trading before the American Civil War in 1861.
[4][5][2] Tough joined the "Red Legs" guerrilla forces fighting on the Kansas-Missouri Border leading up to the Civil War.
[1][7][8] On July 23, 1863, while at Fort Scott, Kansas, Tough was involved in a disagreement with a Union cavalry soldier named William Gardner.
[5] Following the Civil War, Tough married and settled with his wife at Leavenworth, Kansas, and began operating a livery stable.
[9] Tough then returned to horse trading operating his business at the Kansas City Stockyards and it was reported that he sold a number of animals that were used during the Boer War.