When one thinks of things Kentucky is known for, pirates are pretty far down the list. Kentucky cannot lay claim to any Francis Drake, Bartholomew Roberts, or other famous scallywags from the Golden Age of Piracy. That doesn’t mean there were no Kentucky pirates though! In the late 1700’s and early 1800’s, the Ohio River was one of the major trade highways for the fledgling United States. Where there’s money on the water, there’s bound to be piracy, and Kentucky was a base of operations for several ruthless river raiders.

Samuel Mason

Samuel Ross Mason was born in Virginia Colony in 1739, and he got his criminal start at an early age by trying (and failing) to steal horses as a teenager. He went on to serve as a militia captain during the Revolutionary War, and held several other positions as he slowly moved westward. He was a justice of the peace, and eventually a judge before he moved his family to Red Banks, Kentucky, in the early 1790’s and began his full-time life of river piracy.

By 1797, the Mason Gang was operating out of Cave-in-Rock, a huge cave on the Illinois side of the river that was home to many groups of bandits and pirate over the years. They captured and sank barges from there until they were expelled in 1799 by the Exterminators, a group of regulators led by Captain Young of Mercer County, Kentucky.

Mason moved his gang and his family to Spanish Louisiana Territory (in what is now Missouri and Mississippi). It was here as a highwayman that he reached the height of his infamy. He would leave a message after each crime, often in the blood of his murdered victims, proudly stating, “Done by Mason of the Woods”.

Eventually Mason and his gang were captured by Spanish officials and extradited to US territory since all their crimes had been committed in US territory. Mason and a couple of his more notorious men (Wiley “Little” Harpe who along with his brother has the distinction of being America’s first serial killer, and Peter Alston the notorious counterfeiter) escaped while being transported, but Mason was shot in the attempt. A reward was immediately issued for their recapture, and Harpe and Alston brought Mason’s head in attempting to collect the reward.

It’s unclear whether the two killed Mason themselves or if he eventually died of the gunshot from the escape, but Harpe and Alston were recognized and captured. They were convicted of Mason’s murder and put to death in 1804 with their heads on spikes as a warning to other river pirates.

James Ford

Born in 1775, James Ford was significantly younger than Samuel Mason. Ford moved to the Kentucky side of the Ohio River when the Mason Gang was operating out of Cave-in-Rock. He was a civic leader and business owner in western Kentucky and Southern Illinois with a squeaky-clean public image, but secretly he was the leader of what eventually became known as the Ford’s Ferry Gang.

After the Mason Gang was evacuated from Cave-in-Rock, Ford took possession of the cave and ran a ferry boat from there to the Kentucky side of the river. In addition to the usual hijacking of flatboats on the river, Ford regularly had his pirates raid passengers on his own ferry. He may have also operated a tavern and brothel at Cave-in-Rock, though historical records are unclear (It may have actually been a contemporary of Ford’s named James Wilson.)

It is pretty certain, though, that Ford had connections to other well-known criminals of the area. As a substantial land owner, Ford was also a slave owner. His ruthless attitude toward his slaves was well-known, and he had dealings with the notorious illegal slaver John Hart Crenshaw. Crenshaw was heavily involved in the “Reverse Underground Railroad” where free blacks were kidnapped and sold into slavery in the South. Ford also owned the deed to the land that the Sturdivant Gang used as their base of operations. This is interesting considering that Ford served in the 4th Regiment of Illinois Territorial Militia with at least one member of the Sturdivant Gang: James Steele, Sr.

After living for a couple decades with the dual identities of law-abiding businessman and criminal mastermind, James Ford was assassinated in 1833 by unknown vigilantes.