Sam Hildebrand, notorious southeast Missouri guerrilla during the Civil War, became an outlaw after the war. The reasons were many . . .

Sam Hildebrand, notorious southeast Missouri guerrilla during the Civil War, became an outlaw after the war. According to Hildebrand and his apologists, he was driven to a life of crime because  Federal authorities and his Union neighbors would not let him live in peace. Apologists for the James  and Younger  brothers later made a similar claim to try to justify their  unlawful deeds. Of course, there is some truth to the idea that Union authorities and sympathizers made adjusting to civilian life difficult for former guerrillas who chose to return to their former neighborhoods, which is why many of them didn’t return but instead went south. But I doubt that Hildebrand or any of the other guerrillas-turned-outlaws were actually forced into a life of crime.

After the war, Hildebrand lived for a while in Texas, but he was soon back in the Missouri-Arkansas area. Sometime around the early part of 1868,  he allegedly  killed or participated in the killing of a man and woman in northern Arkansas. According to the Hildebrand  legend, as recounted by latter-day apologist Carl Breihan, the man  killed was the former  brother-in-law of a  friend of Hildebrand's. The man had deserted the friend's sister and taken up with a black woman. The friend supposedly asked Hildebrand to help him teach the "guilty pair" a lesson by giving them a flogging, but the man and woman ended up dead from drowning, having been tied together and tossed in a river.  Breihan's reference to the man and woman as the "guilty pair" suggests that, in the Hildebrand myth, deserting one's wife for a black woman was apparently worse than murder. 

Another version of this tale is that the wife-deserter was the husband of a woman who had nursed Hildebrand back to health after he’d been shot and that Hildebrand sought revenge simply because of his high regard for the woman. No mention is made in this version that the woman was the sister of one of Hildebrand’s friends.

Yet another version of the story, recounted in an article in a July 1869 St. Louis  newspaper, said the couple killed was an "old man and his wife," with no indication that it was  a mixed marriage.

Regardless of the exact circumstances of the killing or the exact identities of the people involved, Hildebrand  was arrested after the crime, convicted of murder, and sentenced to be hanged. He was lodged in jail at Pocahontas, Arkansas. (Breihan says Jacksonport.) Sometime in late 1868 or early 1869 just a few days before the scheduled execution date, Hildebrand escaped with the aid of  friends on the outside. According to the newspaper article referenced above,  Hildebrand's cohorts donned the uniforms of  Federal soldiers and arrived at the Pocahontas jail with papers ordering that Hildebrand be turned over the them for "government action." The sheriff complied, and Hildebrand and his friends were long gone before the  fraud was discovered.

Hildebrand returned to  southeast Missouri where he  had lived before the war. Hildebrand’s own story was that he simply wanted to re-establish himself in his old home territory after having been forced to leave at the close of the war, but he also used the opportunity to exact revenge on some of his old enemies and to resume the marauding life he’d led during the war. At the time of the July 1869 newspaper article, Hildebrand had reportedly been "roaming fearless as a lion" and striking terror into local citizens.

Missouri governor Joseph McClurg had just  returned from  a personal trip to St. Francois County. He’d gone there to try to reassure citizens in the area, who were anxious over Hildebrand’s presence, and to help organize posses  to track him down. Some  people even wanted the governor to declare martial law, but he resisted such a measure, because the majority of people opposed it. In fact, in at least one county (perhaps  St. Francois) the governor found that the majority of citizens seemed to be in sympathy with Hildebrand. 

Despite the intense manhunt that continued throughout the summer and fall of 1869, Hildebrand eluded capture. He was finally killed in 1872 across the  Mississippi River in Illinois during a confrontation with law officers, who did not know his identity at the time.

Larry Wood is a freelance writer specializing in the history of Missouri and the Ozarks. You may contact him at or like his author Facebook page at