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 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. On August 31, 1777, he was proven correct when a band of Native Americans from several eastern tribes attacked the fort.
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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 except for Captain Samuel Mason. The captain, however, was severely wounded and escaped death by hiding behind a log. He was soon rescued and recovered from his wounds 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 was named an associate judge just a few months later. In 1782, Mason appeared to be successful, as he paid taxes on his 500-acre farm and 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. His Pennsylvania farm was sold at a sheriff's sale to pay part of his debt the following year. In 1789, the Pennsylvania court sent a man to Kentucky to collect the remaining debt but was unsuccessful.
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By the early 1790s, Mason was settled at Red Banks, now known as Henderson, Kentucky. Later, he moved downriver to 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 several 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 enjoyed the hospitality, Mason's men checked their supplies and goods for anything of value. If they found something, they would wait until the next day and, when the visitors continued, would rob them as they made their way around the bend of the river.
