Short was reported by Bat Masterson to have killed six drunken Sioux Indians at various times. Later writers have relied on Masterson's story as truthful and added to it, but no documentation of these killings has been found. Nonetheless, Short had been in over thirty engagements fighting Indians while working for the government. His first Indian fight was in 1869. Whilst working as a scout for General George Crook in 1876, he was stationed in the Black Hills during the Sioux insurrection. While conducting one of his usual scouting expeditions for the army a band of fifteen Indians suddenly ambushed and fired at him with rifles. Short managed to draw his pistols and fired back, killing three of them in quick succession. Some of the Indians gave chase on horseback, and Short killed two of them before finally reaching safety.