The first military trained gang member was a river pirate in the 1790s. The river pirates conducted similar activities to today’s gangs, with a selection of ambushes, assaults, thefts, and robberies of both travelers and merchants. Perhaps the biggest difference between those gangs and contemporary gangs was their mode of transportation.
Today’s street gang and domestic terrorist group members typically travel by automobile and outlaw bikers travel by motorcycle. As neither had yet been invented, the river pirates of the 1790s traveled by boat, horse, or foot.
Samuel Mason was a militia captain with the Ohio County Militia, part of the Virginia State Forces during the American Revolution. Mason was badly wounded in 1777, when a band of Indians ambushed his party during an attack. All his men were massacred, as were a group that tried to come to their aid. Mason ultimately left the militia and searched for a new career, as many veterans do. In the 1790s, he settled at Red Bank (now Henderson), Kentucky and chose river piracy as his new profession.
Cave in Rock
In 1797, Mason moved his operations to Cave-in-Rock, on the Illinois side of the Ohio River. There, the gang welcomed riverboat travelers, distracting them while other gang members examined their possessions for anything of value. If they found something they wanted, they robbed the visitors as they left the docks. The Mason Gang was forced to leave Cave-in-Rock in 1799 when they were attacked by a group of vigilante bounty hunters.
Sam Mason on the Trace
They moved downriver to the territory known as Spanish Louisiana and became land pirates (highwaymen) on the Natchez Trace, robbing and killing travelers who traversed the 440 miles of wilderness between Nashville, Tennessee and Natchez in the Mississippi Territory. The Trace was often used for return overland travel by folks who had taken a boat down the Mississippi River.
Mason was finally caught in southeastern Missouri, and his trial in a Spanish court resulted in a guilty verdict. Although he escaped during transport shortly thereafter, a $2,500 reward motivated two of his fellow criminals and they brought in Mason’s head in September 1803. Sadly, they were unable to accept the reward money as they, too, were wanted men.
I shot some pics and video on a trip to investigate Mason’s haunts. Here it is: https://youtu.be/fSMT03ihEVs