Getting his start as an honorable man, Samuel Mason served as a militia captain in the American Revolution. Later, however, he would turn pirate on the Ohio and the Mississippi Rivers and lead highwaymen along the Natchez Trace.
Samuel Mason was born in Norfolk, Virginia to a distinguished family on November 8, 1739, and raised in what is now Charles Town, West Virginia. He married Rosanna Dorsey in about 1767 and the couple would eventually have eight children. In 1773, he moved his family to Ohio County, West Virginia. During the American Revolution, he became a captain of the Ohio County Militia, Virginia State Forces in January 1777. He was given command of Fort Henry on the Ohio frontier, in present-day West Virginia.
In the summer of 1777, while colonial soldiers to the east were fighting the war for independence, Mason feared attacks by the Indian allies of the British. He was proven correct on August 31, 1777, when a band of Native Americans from several eastern tribes attacked the fort.
Initially, the Indians fired on several men who were outside the fort rounding up horses. When Mason heard the shots, he gathered 14 men and rode to their rescue. This, however, was exactly what the warriors had hoped for and quickly ambushed the rescue party, killing every last man, with the exception of Captain Samuel Mason. The captain; however, was badly wounded and escaped death by hiding behind a log. He was soon rescued and recovered from his wounds to continue to command Fort Henry for two more years.
In 1779, he moved to Washington County, Pennsylvania, where he bought a 500-acre farm. In July 1781, he was elected justice of the peace and just a few months later, was named as an associate judge. In 1782, Mason appeared to be successful, as he paid taxes on his 500-acre farm as well as two horses, four cows, and six sheep. He also owned four slaves. However, Mason was struggling financially and had become deeply indebted. After having been repeatedly accused of being a thief, he made his way to Kentucky in 1784. The following year, his Pennsylvania farm was sold at a sheriff’s sale to pay part of his debt. In 1789, the Pennsylvania court sent a man to Kentucky to attempt to collect the remaining debt, but, was unsuccessful.
By the early 1790’s, Mason he was settled at Red Banks, now known as Henderson, Kentucky. Later, he moved downriver on Diamond Island, where he began to engage in criminal activity. By 1797, he moved his headquarters further downriver to Cave-in-Rock on the Illinois shore. By this time, he had gathered a number of followers who openly based themselves at Cave-in-Rock. Here, Mason and his men would warmly welcome riverboat travelers to rest and eat. However, while these visitors were enjoying the hospitality, Mason’s men were checking their supplies and goods for anything of value. If they found something, they would wait until the next day and when the visitors continued on, would rob them as they made their way around the bend of the river.
While at Cave-in-Rock, Mason and his men briefly harbored the notorious Harpe brothers, who were on the run from the law. The Harpes were a couple of the most brutal outlaws at the time and distinguished themselves as being America’s first serial killers. Though the Mason Gang could be ruthless, even they were appalled at the actions of the Harpes. After the murderous pair began to make a habit of taking travelers to the top of the bluff, stripping them naked, and throwing them off, they were asked to leave.
In the summer of 1799, the Mason Gang was forced to leave Cave-in-Rock when they were attacked by a group called the “Exterminators.” This group of vigilante bounty-hunters was led by Captain Young of Mercer County, Kentucky. Mason then moved his operations downriver and settled his family in Spanish Louisiana and became a highwayman on the Natchez Trace in Mississippi, robbing and killing unsuspecting travelers.