In the early days on the Kentucky frontier, few if any frontiersmen exceeded Simon Kenton in stature or reputation. Described as a “giant of a man” at a muscular 6 feet, 3 inches, he became known as the “savior” of the early settlers and the bane of the region’s hostile tribes. His experiences rivaled—and, in some instances, outstripped—those of his more widely acknowledged friend, Daniel Boone.
As a teenager, Kenton, believing he had killed a man in a fight, fled his native Virginia for the wilds of Kentucky, assuming the surname Butler. Over the next few years, he attained a widespread reputation as an able hunter and fighter of American Indians, using his skills to provide for, guide and protect newcomers. And when the region’s native tribes rose in response to the influx of settlers, the governor of Virginia—which included Kentucky at the time—called upon Kenton to serve as scout for the militia.
Acting as guide for the 400-man militia party under Col. Angus McDonald, Kenton was instrumental in the destruction of several hostile Shawnee villages during the brief Anglo/Indian conflict known as Lord Dunmore’s War. At the conclusion of hostilities in October 1774, the defeated Shawnee agreed to give up their claims to the lands south and east of the Ohio River and to refrain from further harassing white travelers. For the moment, at least, it was a victory for Anglo expansion into the region constituting present-day West Virginia, southwestern Pennsylvania and Kentucky.
The peace would prove short-lived. Kenton later recalled, “[I]n 1776, the Indians became very harsh on us.” By the time relations between Great Britain and her North American colonies led to open war, certain disaffected Shawnee bands joined forces with the Cherokee under Chief Dragging Canoe and renewed their hostilities against the white interlopers. The region—of which Kentucky comprised a large part—was far from pacified.

Finding the Canelands
Kenton left the military and went again in search of Kentucky’s elusive, legendary Canelands. This time, after nearly a year spent paddling hundreds of miles on the Ohio River and with the help of a French trader who knew the region well, he was successful.
The Canelands proved as rich in game and arable soil as Kenton’s late partner, Jacob Yeager, had described four years earlier. For the first time, Kenton claimed land of his own on Limestone Creek, taking “planting possession” of an idyllic spring-fed site at the edge of the canebrake by making “tomahawk improvements”—notching the letter “K” into the surrounding trees. The country was a hunter’s delight, teeming with buffalo, deer, bears, and birds of every description.
It also was ideal land for farming. Kenton built a cabin, cleared an acre, and planted corn, just as the various regional tribes had done for generations. According to biographer and descendant Edna Kenton, he “raised the first crop of corn ever cultivated by white men north of the Kentucky River” on land that one day would become Mason County. For the next several years, Kenton used this spot as his home base, from which he staged countless raids during the coming Indian Wars.
Aware of the land investment possibilities, Kenton soon extended his holdings. However, as he had discovered early in his Virginia boyhood, his interest never lay in farming. He was young and footloose in a newly opened section of the country that begged for exploration.
By the time Kenton discovered the Canelands in the spring of 1775, he was far from the only white man in the region. Surveyors and agents representing ambitious land speculators were honeycombing Kentucky, seeking to stake it out for development. One such enterprise, calling itself the Transylvania Company, hired as its agent no less a personage than Daniel Boone, whose assignment was to range throughout Kentucky and negotiate with the Indians for the sale of their lands. In an apparent violation of existing laws severely restricting individual ownership of uninhabited frontier land, the company’s principal, North Carolina Judge Richard Henderson, signed a treaty with the Cherokee in which he bought some 20 million acres in exchange for around $10,000 worth of trade goods.
Soon, settlers and investors were purchasing land from the large companies or simply staking their own claims. Forted communities— “stations,” such as Boone’s Boonesborough—began to spring up. Kenton spent several months visiting the settlements, acquainting himself with the new settlers.
Once again, Kenton assumed his unofficial role as welcomer, hunter, protector and guide. Limestone Creek, on which he had established his permanent camp, became known as the best landing spot for the dozens of parties now traveling downriver, and Kenton was there to greet them. Biographer Kenton points out that it is incalculable “what it meant in those days to land on a strange shore and find there a tall … smiling young man who walked like an Indian and looked and dressed like one, who spoke confidently of trails and distances … who knew exactly how to lead the newcomers to Harrodsburg, Boonesborough, McClellan’s, Huston’s, and Hinkston’s forts, who knew all the men at all these stations, and who could give offhand all the facts of their numbers and achievements to date.”
In his 1812 History of Kentucky, Humphrey Marshall wrote, “Thus, [Kenton] became acquainted with the first settlers in the country; to whom he was everywhere serviceable; and with whom he everywhere partook of danger.” At times, this involved bitter fighting with the Indians, who knew him as “Bahdler,” and feared and respected him as a fierce adversary.
Saving a Friend
Kenton and Boone became close friends, and, for a time, Kenton used Boonesborough as a base of operations, serving as hunter and chief scout for the settlement. He provided food for the inhabitants and warned of impending Indian raids.
In the spring of 1777, around 100 Shawnee under Chief Black Fish laid siege to the fort, placing a strain on its food and fuel supplies. Kenton and Boone sent two men outside the palisades to find food and firewood. They had progressed only as far as the tree line when a small party of Shawnee warriors emerged from the woods, scalping knives in hand, killing one and seriously wounding the other. Kenton, Boone and a party of 10 settlers immediately left the fort in a rescue attempt.
It was a trap. A large group of warriors immediately left the trees and attacked the rescue party, cutting them off from the fort. Almost at once, seven men were wounded. Boone went down with a bullet-shattered ankle as a warrior approached him with an upraised tomahawk. Seeing his friend helpless on the ground, Kenton shot the Indian, scooped Boone up in his arms, and ran back through the gates of the fort. According to some accounts, while returning to the fort with his injured friend slung over his shoulder, Kenton was confronted by two Shawnee warriors. Unable to draw his knife or tomahawk and with no other means of defense, he simply threw Boone at them, knocking both down and rendering one of the two unconscious. Hands now free, he brought his tomahawk down on the other’s head, retrieved his friend, and carried him to safety.
The siege lasted another four weeks, with the settlers’ crops unattended in the field and the Shawnee killing off their cattle and stealing their horses. During this time, Kenton repeatedly left the fort to hunt for food, each time at great risk of losing his life.
Word of Kenton’s dramatic rescue rapidly swept throughout the frontier, and soon those few who might not have been acquainted with it before now knew the name “Kenton Butler.” He was, however, just as well known among his Shawnee enemies, and, in a short time, he would suffer terribly at their hands.
A “Guest” of the Shawnee
In the fall of 1778, Kenton and two others set out to retrieve some horses that the Shawnee had stolen. Recapturing the animals, they made it back as far as Eagle Creek, a tributary of the Ohio River. As they looked for a suitable crossing, a war party of mounted Shawnee under Bo-Nah attacked, killing and scalping one man and seizing Kenton. The third managed to escape into the woods.
Kenton’s tenure as a prisoner of the Shawnee would tax his endurance to the limit. At first, the Indians were unaware that they had captured their greatest foe. The next morning, another war party arrived and recognized the captive. What followed was the stuff of nightmares.
First, Kenton was tied to the back of an unbroken horse, a halter joining his neck to the horse’s neck and rump. The animal was then whipped, whereupon it galloped through the trees and bushes trying to dislodge its burden. Wrote biographer Kenton, “[T]he ragged bushes tore its rider’s legs and feet; the tree limbs raked and scourged his face and body.” If Kenton lost his balance and fell off the horse, the halter would strangle him. Finally, the horse slowed and stopped.
Kenton then was taken to Bo-Nah’s village, where he was stripped and made to run a gauntlet. This was a standard form of torture for prisoners. The entire village turned out, forming two long lines—at the head, the women and children, then the warriors. Everyone held a stick or club, and the victim was forced to run the length of the line as blows repeatedly were rained on his naked body. If he fell, the beatings and kicking simply continued.
At the end of the line stood the council house. If the prisoner succeeded in making it there, he was temporarily untouchable while the elders decided his fate. In some instances, he would be adopted into the tribe, as Boone himself had been the year before. He might be made a tribal slave, or—since the Revolutionary War was raging and a number of tribes had allied with Great Britain against the hated colonials—he might be sold or traded to the British. In some instances, death would be prescribed—and a horrific death it would be.
Taking terrible punishment as he ran the quarter-mile-long gauntlet, Kenton nearly reached the council house when a terrific blow across the back of his legs tripped him. He fell and was beaten senseless. When he regained consciousness, he was made to run the gauntlet a second time.
Traditionally, this was unheard of. Prisoners were made to run the gauntlet only once. After Kenton survived his second gauntlet, Bo-Nah took him to several other Shawnee villages to show off his famous captive. Given time to recover between each ordeal, Kenton was made to run the gauntlet at each village Bo-Nah visited.
Mac-A-Cheek, one of the largest of the Shawnee villages, was located in present-day Logan County, Ohio. Kenton was taken there to run yet another gauntlet. Assuming that he would not long survive the Shawnees’ treatment, he determined to make his escape during this run. As he raced between the rows of villagers, he ran directly at an old woman, bowling her over and dashing into the surrounding woods. A fast runner, he had left the surprised villagers well behind when he practically ran into a war party led by Chief Blue Jacket. The chief, who had been riding to the village to view the famous prisoner, rode Kenton down, bringing the round pipe end of his iron tomahawk down on the fugitive’s head.
The blow drove a hole into Kenton’s skull, rendering him senseless. Writes his biographer, “Kenton bore this indentation, as large as a dollar, to his last day.” Incredibly, he survived, but did not regain consciousness for days. When he had recovered sufficiently, he was taken to Wapatomica, the home of Black Hoof, principal chief of the Shawnee, and the site of several intertribal councils. There, it was determined that Kenton would run his final gauntlet, after which he would suffer death by being burned at the stake. “It was … decided,” writes Edna Kenton, “to make the ritual a national rather than a local affair,” and Indians from far-flung villages poured into Wapatomica to watch Bahdler die.
As was the custom, Kenton was painted black and referred to as “Cutahota,” meaning “the condemned.” Escape was out of the question, and it seemed as though his future held only a terrible end. Kenton later commented, “When the sentence of death was pronounced on me, with eternity apparently just before me, I felt like it was cutting me off mighty short.”
After running his final gauntlet, Kenton was tied to the stake and the fuel lighted, when a sudden cloudburst drenched the proceedings. The execution was postponed until the next day. It was at this time that Simon Girty entered the village as a member of a Shawnee war party.
The two Simons had established a strong friendship years earlier, becoming blood brothers and swearing lifetime loyalty to one another. Since that time, Girty, who had been taken by the Shawnee as a small child and raised among them before returning to Anglo society, had chosen to side with his adopted tribe and their British allies during the Revolution. As a result, he became the most hated man in the colonies, vilified as the “White Savage” and hunted as an enemy to his people.
His bond of friendship with Kenton remained firm. When he recognized the face-blackened Butler, Kenton later recalled, “O, he was mighty glad to see me; he flung his arms around me and cried like a child.”
Girty spoke to the tribal elders and begged a favor: the life of his friend. After some debate, the tribe voted overwhelmingly to give Kenton his freedom. As Edna Kenton writes, now that he no longer faced imminent death, Kenton was treated as an honored guest. “[T]he warriors gathered about him, each heartily shaking his hand, each calling him ‘Brother,’ each expressing admiration of his bravery, his running, his leaping, his cunning, his pride of spirit.” Further, “Kenton was adopted by an old [woman] to replace a slain son.”
Girty outfitted his friend and took him on a tour of the surrounding country. Over the next three weeks, Kenton recovered his strength only to discover that a recently defeated war party had entered the village. Brooding over a loss of warriors and furious that a hated enemy had been reprieved, they demanded a reversal of sentence. This time, Girty could do nothing, and his friend was again sentenced to die at the stake.
It was decided that Kenton should be executed in Sandusky, 50 miles distant, so that members of several other tribes could attend. On the way, a warrior struck Kenton with his war club with sufficient force to break his upper arm. Farther along the journey, another brave swung his ax into Kenton’s collarbone, fracturing it as well.
Despite his injuries, he was again forced to run a gauntlet—his ninth— and to be staked out naked on the ground at night, his broken arm and shoulder a constant agony. When the party reached Sandusky, preparations for Kenton’s death again were made. And again, fate intervened. Chief Logan, who had befriended Kenton years before, sent a runner to the British fort at Detroit with an urgent plea.
Detroit and Freedom
On the day scheduled for Kenton’s death, a white man suddenly appeared, dressed in the red-and-gold finery of a British officer. He was, in fact, not a member of the British ranks but a trader and interpreter named Pierre Drouillard—and the man responsible for doling out British presents to their Indian allies. This was the man to whom Logan had sent his message. In a lengthy speech, he convinced the natives to release Kenton into his custody, to be taken to the British fort at Detroit as a prisoner of war. There, he would be made to reveal the current state of the rebels’ affairs in Kentucky. Kenton, Drouillard promised, would then be returned to the Shawnee for execution of sentence. In exchange, the Indians could claim $100 worth of whiskey, tobacco or any other item of their choosing. The Shawnee elders reluctantly loaned Drouillard their captive.
In Detroit, Kenton received long-neglected medical attention, requiring his arm to be rebroken and set. He was allowed to roam the town at will, provided he report to the commander every Sunday and not attempt to escape. Kenton remained in Detroit until the spring of 1779, several months after his initial capture. During this time, he was permitted to attend council meetings in which various tribal allies would submit Patriot scalps for bounty. The commander, Kenton recalled, encouraged the practice, at one point taking a warrior’s tomahawk in hand and “pretending to whet it, said, you have dulled it and now it is sharp, go and dull it again.”
During the months of his captivity in Detroit, Kenton was carefully planning his escape. George Rogers Clark, Kenton’s friend and leader of the Kentucky militia, would benefit immeasurably from the intelligence Kenton was gathering regarding British strength and plans. But first, Kenton would have to make his way back to Kentucky.
Kenton struck up a friendship with a sympathetic Detroit merchant, who helped him procure a rifle, powder, shot, moccasins, and a store of dried deer and buffalo meat, which Kenton cached in a hollow tree outside the town. In early June, he sneaked out of Detroit along with two fellow prisoners. His friend had advised him to travel west for a considerable distance before turning south toward Kentucky; to travel due south from Detroit was to invite capture by Indians on any trail he took.
In July 1779, after traveling for a harrowing 30 days through 400 miles of trackless wilderness, the three arrived safely at the Falls of the Ohio. They were wise to have taken the western route; although his former captors—aware that he had escaped—were on the lookout for him on every westbound trail out of Detroit, Kenton later recalled, “We didn’t see an Injun on all our journey to the Ohio.”
Kenton immediately transmitted the intelligence he had gathered to Clark. Then, after a long absence, he returned to his own camp on Limestone Creek. By this time, Kentucky was boasting several new settlements and was rife with surveyors and land grabbers. In response to the influx of Anglos, the Indians were renewing their attacks. That winter, Kenton built a blockhouse at the mouth of the creek as a shelter for the settlers and newcomers.
A number of the new arrivals hailed from Fauquier County, Virginia, Kenton’s old home—and some of them recognized him, despite his assumed name. At some point, he inquired after his family, and—tactfully—that of William Leachman, the man he had felled and presumably killed in hand-to-hand fighting several years earlier. He was stunned to learn that Leachman was alive and had, in fact, been accused of murdering him! Kenton had simply vanished after the fight, and it was widely assumed that Leachman had slain him and hidden the body.
Relieved to learn that he was not a murderer, he again became—and for the rest of his life would remain—Simon Kenton.
Coming in Part Three:
Kenton continues to guide for Gen. George Rogers Clark throughout the war and to scout for Gen. “Mad Anthony” Wayne during the Northwest Indian War of 1794. He acquires thousands of acres in Kentucky and Ohio, only to lose it to scoundrels and thieves. He serves as a brigadier general of militia in the War of 1812, and, on more than one occasion, he finds himself imprisoned for debt by the same people whose lives he had once protected. Plus, he finds time to marry twice and to sire a prodigious family.