As Merrideth says in How Sweet the Sound, Samuel Mason is a conundrum. The information to be found about him is contradictory, the facts slippery to hold onto. Even the descriptions of his personal appearance vary widely:
He weighed about two hundred pounds, and was a fine looking man. He was rather modest and unassuming, and had nothing of the raw-head-and-bloody-bones appearance which his character would indicate.
—John L. Swaney, Old Times in Tennessee. Nashville. 1878.
Mason at any time of his life or in any situation had something extremely ferocious in his look, which arose particulary from a tooth which projected forwares, and could only be covered with his lip by effort.
—William Darby. “Notes on Western Border Life” Casket Magazine. Philadelphia. 1834
Otto Rothert calls him a “ gentleman outlaw” who didn’t rob anyone if they were from Ohio County where he grew up. Or if he did rob them, he at left them with enough money to get home. Rothert describes Mason as “one of the shrewdest and most resourceful of outlaws. And unlike the sociopaths Macajah and Wiley Harpe who killed for fun, Mason “never shed blood unless it became absolutely necessary for his own safety.”
But in spite of Rothert’s assessment, Mason’s deeds reveal that he was quite ruthless. It is not known how many people he murdered. Mason and his gang are considered by many to be Illinois’ first organized crime syndicate.
Mason was born in 1750 to a respected Virginia family. His sister married a Methodist minister. One brother was an ironmaster. Another brother rose to the rank of colonel in the army and was revered. In later years Mason’s family disassociated itself from its black sheep, and tried to metaphorically “tear his branch from the family tree.” (Rothert)
Samuel Mason’s life was a contradiction. As a young man he stole horses in West Virginia, and in Tennessee he robbed the shacks of slaves while they were at church. But he also earned commendation as a brave soldier during the Revolutionary War. Two of his brothers served with George Rogers Clark on the western frontier (Read Once Again for more about these heroes.) Captain Samuel Masson was stationed at Fort Henry at Wheeling, West Virginia. While there he stole supplies (I could find no mention of any consequences) but on another occasion, he and fourteen men courageously fought a force of 400 attacking Indians. Fellow officer Captain Joseph Ogle led twelve troops out to rescue them. All but five of their men were slaughtered and Mason and Ogle were both severely wounded. Captain Ogle went on to become one of the renowned early pioneers of my own Monroe County, Illinois, and I mention him in Once Again. Captain Mason was destined for another future entirely.
Samuel Mason retired from active military service and bought a farm in 1779, the same year his father Thomas Mason died, leaving him five shillings. In 1781 he was elected justice of the peace for Washington County, Kentucky and then associate judge the same year. He married Rosanna Dorsey, and eventually they had six sons and four daughters. The tax records show that in 1782 Samuel Mason had 500 acres, two horses, four cows, six sheep, and four slaves.
But apparently Samuel Mason wasn’t cut out for farming. He ran up debts in Washington County and the farm was sold by the sheriff in 1785. After that, Mason turned to criminal ways of earning a living and found that he was much better at being an outlaw than he was a farmer. In 1790 he and the family moved to Red Banks, now Henderson, Kentucky. The Masons were some of the first settlers there. Other outcasts joined them there, and it became a haven for the lawless. When a “commission of peace,” was sent to keep order there, Mason and the others said no thanks and drove them away.
Benjamin Van Cleve, passing through Red Banks on his way from Cincinnati to Fort Massac, recorded the following in his diary:
This place is a refuge, not for the oppressed, but for all the horse thieves, rogues, and outlaws that have been able to effect their escape from justice in the neighboring states. Neither law nor gospel has been able to reach here yet.
At Red Banks Mason turned completely to the dark side and became a leader of outlaws. Rothert theorizes that living on the frontier turned good men into bad ones. I took exception to that statement when I first read it. But then I remembered what happened in the book Lord of the Flies. A plane carrying a group of wholesome English schoolboys crashes on a deserted island. After a while, with no regulating forces in place, the boys become complete barbarians. But I don’t think for one minute that the boys in Lord of the Flies or Samuel Mason in real life were changed by their surroundings into different people. It’s just that without the restraining influence of the Holy Spirit, they let their sinful natures (the ones all Adam’s sons and daughters possess) run amok. Eventually, Christians brought the gospel to the lawless frontier, and evil was, to a degree, restrained. I tried to portray this concept in How Sweet the Sound near the end when Trevor and his friends hold a chapel service in the cave.
Trevor held out his arms to show the words of Amazing Grace tattooed there. “Newton wasn’t exaggerating when he described himself as a ‘wretch.’ But I was no less a wretch than he. And that day God saved me, too.”
Trevor began to sing the words, and once again the hymn filled the cave, as if he were staking a claim on it for the kingdom and casting out its demons once and for all.
Some of Mason’s sons participated in his criminal endeavors at Red Banks, although Rothert reports that most of his children lived respectable lives elsewhere. The only representative of the law for the whole lawless region was Constable John Dunn. Mason ran afoul of him on several occasions, once when Dunn wouldn’t go along with one of his plans, and once when Mason stole a Negro family from a man named Knox. (Later as a river pirate Mason often stole slaves and sold them along with the cargo he confiscated from travelers.) The conflict between Mason and Constable Dunn escalated and finally one of Mason’s men killed him, presumably on Mason’s orders.
Kentucky citizens on the settled, eastern side of of the state were getting sick and tired of the lawlessness on their western border and organized “Regulators” to clean house. (You can read more about the regulators HERE.) Mason and other outlaws fled ahead of them westward across the Ohio River into Illinois. His next base of operations was on Diamond Island where he first began to prey on the settlers coming down the river. He managed a whole network of spies who passed word about approaching boats and their cargoes. In 1797, Mason took on the alias “Wilson” and again moved headquarters downriver, this time to Cave-in-Rock.
Business boomed for him, because news of piracy on the Ohio was not widely circulated at that time. But travelers had been warned of dangerous channels and currents in the river and advised to hire locals to steer them around them. One of Mason’s techniques was to have his men pose as river guides who then ran the boats aground. Another method was to have one of his men sneak onboard and take the chinking out of the bottom of a boat. When it started to sink, the gang would kindly help the travelers unload their goods on shore. Sometimes, as in How Sweet the Sound,they lured the boats to shore with women as decoys-either as damsels in distress or with the promise of lascivious entertainment in the cave. Mason attempted to manage the robbery in such a way that blame was not cast on him or associated with the cave. Sometimes, as in How Sweet the Sound, things went wrong.
Eventually word got out, and Pittsburgh merchants hired private investigators to go find out why their merchandise was not making it to New Orleans but kept disappearing on that particular stretch of the river. When they came snooping around, Mason left his den and moved farther down river to the mouth of Cache River near the confluence of the Ohio and Mississippi at Cairo, Illinois. The little story I include in How Sweet the Sound about “bobbing” comes from the Cache River area, although I’m not certain if the practitioners of this fun little pastime were some of Mason’s men or other pirates operating there.
With the law on his trail, Mason gave up river piracy altogether in 1800 and turned his attention to robbing travelers on the Natchez Trace, the main route between Nashville and Natchez, Mississippi with access to the New Orleans markets. It was a lucrative business for Mason. Until the governor of Mississippi put a $500 bounty on his head.
In 1803, some of his own men killed him for the reward, and taking that wording literally, cut off his head and delivered it to the authorities for the reward. One of the men was recognized as Wiley “Little” Harpe, and like his outlaw brother four years earlier, he was captured and beheaded, his head put on a pike to warn other outlaws to give up their evil ways.
It must have worked. After that, law and order generally prevailed, and by 1830 piracy on the Ohio River had ceased.
http://www.chartiers.com/raybell/1995-mason.html (Raymond Bell Anthology)
The Outlaws of Cave in Rock. Otto A. Rothert. 1924.
“Sam Mason: Two Accounts.” The Springhouse. Vol. 10 No. 3. June 1993.