The story of Samuel Ross Mason.
When you hear the word “pirate,” you might think of Johnny Depp in the Pirates of the Caribbean, the celluloid swashbuckler and dashing adventurer. But true piracy most often attracted men of few scruples and those with a skewed moral compass who were driven by a lust for gain and had an inclination toward violence. These ruthless cutthroats were the scourge not only of the blue waters of oceans and seas but also of big rivers.
In the years following the American Revolution, there was a virtual epidemic of piracy on and along the Missouri, Mississippi, Ohio, and Illinois Rivers. These so-called “river pirates” preyed upon travelers on both the brown water and traces (or narrow roads) that often ran along rivers. All traffic, from keelboats to riverboats, and all who journeyed, from solitary travelers to horsedrawn coaches, were susceptible. The most favorable scenario for sojourners who were waylaid by these brigands was simply to be lightened of their purses and allowed to continue on their journey; at worst, they would lose their lives as well as their property. After a robbery or murder, the pirates would simply disappear with impunity into the endless forests or rock-faced mountains.
One of the most notorious of the river pirates, who at times operated in Missouri, was Samuel Ross Mason.
By 1800, a reward of $2,000 had been posted on his head. He moved operations from the Ohio River, establishing a base on Wolf Island on the Mississippi, about 50 miles southeast of Cape Girardeau and near the confluence of the Mississippi and Ohio Rivers. The unincorporated community at Wolf Island today is likely close to where the base was in the Mississippi River.
Gentleman Turns Killer
On the surface, Sam seemed the unlikeliest person to become an outlaw. Born in late 1739 to a prominent Virginia family, Sam had been afforded all the privileges of his class. He married a respectable woman and, over time, fathered eight children. When the Revolutionary War broke out, he volunteered and was made a captain in the Virginia State Forces. Sam was soon placed in command of Fort Henry on the Ohio frontier.
The region was rife with British-allied Native American tribes, and in late August 1777, Captain Mason and his command were lured into a trap in which everyone but Sam was killed. Seriously wounded, he survived by hiding behind a log. Upon his recovery, he was again assigned command of the fort, serving in this position for another two years. He apparently served with distinction. As Otto A. Rothert, author of The Outlaws of Cave-in-Rock states, “Captain Mason participated in several campaigns to defend frontier settlements from British-allied Native American tribes. … His leadership was particularly notable during the western campaigns, where he operated in volatile and unforgiving terrain.”
The type of warfare waged on the frontier was unimaginably brutal. Both sides offered significant bounties for scalps—White and American Indian. There were those who made a living in obtaining scalps. In Carter F. Smith’s article, “Samuel Mason: Revolutionary Turncoat or Opportunistic Pirate?” published in the Journal of the American Revolution, he observes that Sam’s experiences “likely exposed him to the harsh realities of frontier warfare, shaping his worldview and preparing him for the life of an outlaw.”
In 1779, Sam moved his family to a 500acre farm in Pennsylvania, where he initially prospered. Within two years, he was elected justice of the peace and named an associate judge. However, he went heavily into debt and fled to Kentucky, where he formed a gang of brigands, which would come to include his four sons. They began preying on travelers on the Ohio and Mississippi Rivers.
Sam established a headquarters at Cave-in-Rock, a deep, wide natural cavern overlooking a bend in the Ohio River on the Illinois side of the border between present-day Illinois and Kentucky. From here, he would watch for river craft, most often flatboats, hauling goods and passengers. To lure crews to the shore, sometimes a gang member would pretend to be a stranded local or else a navigator offering to help negotiate the often turbulent stretches of river. On other occasions, Sam’s female accomplices would tempt the crews ashore and ply them generally either sunk or sold. (In the epic 1962 film How the West Was Won, Walter Brennan plays a Sam Mason-like character, who lures an unsuspecting fur trapper, played by James Stewart, into his well-stocked cave, only to rob him and attempt to kill him.)
Concerted efforts were made to catch the pirate leader, but his knowledge of the countryside helped him avoid capture. That $2,000 bounty on his head at the turn of the 19th century was a stunning amount, about $51,000 in today’s money. When a self-appointed group of vigilantes calling themselves the Exterminators came after Sam, he abandoned Cave-In-Rock and moved operations downriver to the strategically located Wolf Island on the Mississippi River southeast of Cape Girardeau.
At one point, Sam diversified, and along with his gang, he began to ply his trade as a land pirate. He focused his activities on the infamous Natchez Trace, an ancient Indian traveling and trading path that now runs some 450 miles as a scenic parkway from Nashville, Tennessee, to Natchez, Mississippi. In the early 1800s, it was arguably the most dangerous travel path in North America, upon which robbery, murder, and kidnapping were frequent occurrences. Furthermore, boundaries between areas governed by different countries were vague, and the question of jurisdiction among the Spanish, French, and Americans was, at the very least, confusing. As a result, relatively few miscreants were captured.
Cave-In-Rock, which was also used by other outlaws, has become Cave-In-Rock State Park in Illinois. The cave is within the heavily wooded park, which has high bluffs overlooking the Ohio River. Local lore claims Frank and Jesse James left their marks in the cave after the Civil War, and various visitors have reported sightings of the ghost of Sam Mason.
The Posse Captures Sam
Finally, Sam’s luck ran out. By early 1803, Mississippi Territorial Governor William C. C. Claiborne, driven to action by a wealthy and prominent Revolutionary War veteran whom Sam had robbed, took significant steps to catch him; he dispatched Colonel militia leader Daniel Burnet with orders to capture the bandit and his gang, writing, “These Men must be arrested; the honor of our country, the interest of society, and the feelings of humanity, proclaim that it is time to stop their career. … [I]mmediately endeavor to procure 15 or 20 men as volunteers and place yourself … at their head.”
The governor added, “If you should fall in with Mason and his party, you will use all the means in your power to arrest them … and I desire, that the person or persons arrested, may immediately be conveyed under a strong guard to Natchez.”
Word had spread that Sam had been seen in the neighborhood of Little Prairie, present-day Caruthersville. The governor’s posse found the cabin in which Sam, eight men, and one woman were living. The lawmen surrounded the cabin and arrested the gang without mishap.
Sam and his cohorts were sent in chains to the Spanish authorities in New Madrid (in present-day Missouri) for trial, where they faced numerous charges, including piracy, robbery, forgery, kidnapping, and murder. Although Sam reportedly claimed to be a guiltless farmer, in Kathy Alexander’s book, Legends of America, an opposing view is shown. Kathy states that “the presence of $7,000 in currency and 20 human scalps in his baggage convinced [the court] he was guilty.” Scalps aside, the $7,000 found in his belongings would be valued today at over $177,000.
The Pirates Escape
Once again, the murky issue of jurisdiction arose. Sam and his gang were sent to New Orleans to appear before the Spanish authorities, who determined that the case, in fact, should be adjudicated by the Americans. Sam and his gang were placed aboard a ship, this time to face trial in Natchez, Mississippi. Along the way, they staged a daring escape. In the gunfight that ensued, Sam was wounded in the head but escaped and survived.
The governor then raised the reward to a stunning $2,500—more than $60,000 in today’s money. This time, the Spanish government also offered a reward for Sam, dead or alive, and the manhunt grew into a frenzy. Ultimately, the reward proved too tempting for two of Sam’s long-time confederates.
One day, they appeared before the authorities in Old Greenville, Mississippi, with a severed head preserved in a ball of clay, claiming it was that of Samuel Mason. Others, including Sam’s wife, did not agree. The conflicting testimonies carried enough weight with the court to discredit the bounty hunters’ claim. Rather than receiving the reward, the two were arrested, tried, and hanged for their own crimes, and their heads were mounted on poles on the Natchez Trace as a warning to would-be miscreants.
Since there was no legally recognized acknowledgment of Sam’s death, the story entered the realm of folklore. As with such notable outlaws as Jesse James and Billy the Kid, word of sightings persisted, many placing Sam somewhere in Canada. Other stories had Sam dying from wounds he received in his escape. Whatever the resolution, the region’s rivers had seen the last of Samuel Mason and his gang of cutthroats.
Although oral tradition and lore would portray Sam as a heroic outlaw fighting against authority, he was far from a courtly highwayman. Samuel Mason was nothing more than a former war hero who abandoned that course of life to take on the mantle of thief and murderer.
This article was originally published in the July/August 2025 edition of Missouri Life.
Photos were created by Artificial Intelligence.
