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From 1861 to 1865, war-torn Missouri produced its share of guerrillas and brigands. The deeds of many Missourians who rode “under the black flag”—“Bushwhacker Bill” Wilson, Cole Younger, and “Little Arch” Clement, to name just a few—fell far outside the bounds of what were considered the “acceptable” rules of conduct during wartime. One man who stood out among this company for his unbridled dedication to mayhem was Sam Hildebrand, known as the “Big River Bushwhacker.”

Not surprisingly, Hildebrand claimed to have been “driven to it” by outrages committed against him and his family. It was the same assertion that was echoed by the Jameses and the Youngers, among others: Frank and Jesse James pointed to the near-fatal hanging of their stepfather by Union soldiers, while Cole Younger and his siblings used the murder of their father as justification for their guerrilla and outlaw careers.

Samuel S. Hildebrand was born on January 6, 1836, to a large farming family near Big River in St. Francois County in southeastern Missouri. He married at 18, and in short order, fathered six children. The most commonly referenced photograph of Hildebrand, likely taken during the war, features the bearded 6-footer standing at attention, incongruously clad in what appears to be a Union coat and forage cap, with a brace of Colt revolvers in his belt.

Unlike other guerrilla fighters who survived the war, the completely illiterate Hildebrand dictated his autobiography, which was published in 1870, just two years before his death. It sports an impressive if immodest title, the first part of which reads: Autobiography of Samuel S. Hildebrand, the Renowned Missouri “Bushwhacker” and Unconquerable Rob Roy of America Being His Complete Confession. Despite its burdensome title, it is a well-illustrated, remarkably lucid, and highly entertaining 300-page tome, detailing the impetus behind Hildebrand’s career as a bushwhacker, as well as his actions during the war.

This warrant to have Samuel Hildebrand arrested for murder was issued on June 3, 1865, in St. Francois County, Mo. If caught, Hildebrand was ordered to be held until a scheduled November trial. (Missouri State Archives)

According to Hildebrand, his brother Frank—whom he felt had been erroneously accused of horse stealing—attempted to enlist in a Union Home Guard outfit in October 1861 but was instead turned over to the local vigilance committee, an entity created in assorted parts of the country to administer justice when citizens felt government authorities were inadequate. The committee’s leader, Firmin McIlvaine, unhappy with a local justice’s refusal to act without sufficient evidence, took matters into his own hands.

“The sad termination of the affair,” Hildebrand recalled, “is soon told. The mob took my kind, inoffensive brother about five miles and hung him without any trial whatever, after which they threw his body in a sink-hole thirty feet in depth, and there his body laid for more than a month before it was found.”

Hildebrand, who would assert he had also been falsely implicated in the horse-stealing charges, had been hiding in the local woods. He returned home to find his house ransacked by the committee, and his possessions either taken or destroyed. “I was completely broken up,” he recalled.

Nevertheless, Hildebrand claimed to have eschewed violence, choosing instead to devote himself to supporting his family, “provided I could do so without being molested.” The vigilance committee, however, was soon elevated to the status of a Union militia company, going after locals it considered disloyal. They raided Hildebrand’s farm again, pursuing him into the woods and wounding him in the leg.

Hiding under a pile of leaves, Hildebrand swore revenge, seeing himself as doubly wronged. “As I lay in that gully, suffering with my wounds inflicted by United States soldiers, I declared war. I determined to fight it out with them, and by the assistance of my faithful gun, ‘Kill-devil,’ to destroy as many of my blood-thirsty enemies as I possibly could….[F]or the sake of revenge, I pronounced myself a Rebel.”

Word of Hildebrand’s situation soon spread to a local company of Rebel guerrillas under Captain Nathan Bolin, and the wounded Hildebrand was soon spirited away to the Confederate camp across the state line in Arkansas. According to Hildebrand’s account, Captain Bolin explained, “We are what is denominated ‘Bushwhackers’; we carry on a war against our enemies by shooting them.”

Hildebrand was soon introduced to Brig. Gen. M. Jeff Thompson of the Missouri Home Guard. After hearing Hildebrand’s story, the general, who was known throughout the state as the “Swamp Fox,” commissioned him a major on the spot, and ordered him to “go where you please, take what men you can pick up, fight on your own hook, and report to me every six months.” Hildebrand had found his place. “I was fully satisfied that the ‘Bushwhacking department’ was the place for me.”

Hildebrand returned to Missouri with revenge as his primary order of business. His first target was George Cornicius, the man who had betrayed his presence to McIlvaine’s militia company. “After searching two days and two nights I succeeded in shooting him; he was the first man I ever killed; a little notch cut in the stock of my gun was made to commemorate the deed.”

It was the first of dozens to follow. Hildebrand reputedly notched “Kill-devil” whenever he dispatched a man. By the time of Hildebrand’s death, his weapon—a replacement, since Kill-devil had been lost in a Union encounter—reputedly bore between 80 and 100 notches.

Next on Hildebrand’s death list was “the darling object I had in view,” McIlvaine himself. After stalking the militia leader for days, he shot McIlvaine dead as he was harvesting his grain, and carved a second notch in Kill-devil’s stock.

The local Federals took their revenge; unable to find Hildebrand, they raided his homestead, killing his 13-year-old brother, his sister’s fiancé, and an uncle, driving his family out and burning the house to the ground. For Hildebrand, it was now a case of what a proslavery newspaper was calling “war to the knife, and knife to the hilt.”

The rest of the book details Hildebrand’s activities both during and after the war. Not surprisingly, he paints himself in a heroic light, often outnumbered and alone, fighting against Yankee occupation and injustice. Despite the title, it is not a “confession” at all, but rather an indignant self-justification of his conduct.

He ends his autobiography on a grandiose note: 

As several proclamations have been issued against me, without ever eliciting one in return, I shall now swing my hat and proclaim: ‘Peace and good will to all men; a general amnesty toward the United States, and to Uncle Sam—so long as the said Uncle Sam shall behave himself.’

On March 21, 1872, John Ragland, an Illinois constable, and two deputies surprised and arrested what Ragland had been told were three outlaws. One of the outlaws attempted to escape, stabbing Ragland in the leg, whereupon the constable shot the man through the head. Only later did the constable learn that he had killed the notorious Sam Hildebrand.

Future Rebel insurgent Sam Hildebrand was born and raised in this historic farmhouse, now beautifully restored on a 275-acre working cattle ranch in Bonne Terre, Mo., and available to rent through Airbnb. Although the Airbnb listing calls it “a quiet retreat for anyone wanting to get away from the hustle and bustle of city life,” life was anything but quiet here during the war. Vigilantes nearly apprehended both Sam and his brother Frank at their home in the fall of 1861; both barely escaped. Frank was later arrested and hanged. (Courtesy of Bonne Terre)

Hildebrand did, in fact, achieve a measure of hero status, with various Southern-leaning newspapers trumpeting his exploits. Four years after the war ended, and while Hildebrand was still terrorizing Missouri and Illinois, a popular but historically worthless dime novel titled Hildebrand, The Outlaw was printed by Robert M. DeWitt as one of his Dewitt’s Ten Cent Romances (a series that included such “classics” as Sam Sutton, The Scalp Taker, and Old Eph, The Man Grizzly). That effort was followed by an equally absurd release, The Outlaw’s Bride. In neither work does the title character, conjured whole-cloth from the writer’s imagination, bear any resemblance to the man himself.

It is impossible to fact-check many of Hildebrand’s claims. There are few actual biographies, and the various editors of his autobiography are diametrically opposed in their views of him. One edition, published in 2019, introduces Hildebrand’s valiant part in what the editor—who claims a familial connection to Hildebrand—refers to as the “War of Northern Aggression,” leaving little doubt as to where his own sympathies lie.

 “Simply put,” the editor writes, “the Union invaded the Confederacy. The Confederacy was simply defending itself.”

In an earlier edition of Hildebrand’s book, the publisher’s contrasting opinion of his subject is made equally clear: “Hildebrand’s thirst for extrajudicial killing and lack of remorse make him the kind of monster for whom wartime rules of engagement are created….[T]his uneducated, vicious, and vengeful man had no notion of the idea of civilization he professed to believe in.”

Sam Hildebrand entered the war committed to the task of killing Yankees. While most Confederates—regulars and guerrillas alike—returned home in 1865 to rebuild their lives, Hildebrand elected to remain outside the law. He took pride in his reputation as a mankiller, and ultimately he met the same fate as his dozens of victims. 


This article first appeared in America’s Civil War magazine

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