It is equally likely that Quantrill entered Kentucky simply because it had become an Eden for bushwhackers. Killers claiming Southern or Union ties roamed freely in the Bluegrass State, robbing and murdering at will. Dire deeds went unpunished. As Union military control tightened in Missouri, Quantrill sought a land where he could terrorize with impunity. In his search, he found Kentucky. There he would also find his death.

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According to a postwar memoir written by Quantrill scout John McCorkle, the blue uniforms and the Captain Clarke alias easily hoodwinked Federal troops. While riding through Tennessee, the guerrillas were joined by a local Union soldier. As the Federal rode with the men, he pointed out the homes of various Southern sympathizers and jauntily detailed those who should be killed for their disloyalty. Upon reaching one stately home, the soldier pointed and said: “That Rebel that lives there ought not be permitted to live another day. He is rich and the worst Rebel in this country and has done more to aid the damned Rebels than any man in the country.” Hearing the tale, Quantrill turned to guerrilla John Barker and told him to go with the Federal to dispose of the Rebel. McCorkle relates: “John left with our informant and in an hour returned alone, and the rebel who lived on the hill was not molested;…the [Federal] who talked about him never talked about his neighbors anymore.”

The Missourians entered Kentucky in mid-January 1865 near Canton and moved east. On their ride they frequently encountered Northern soldiers. Passing themselves off as Missouri Federals, the guerrillas talked and joked with their enemies. At one point, however, the jovial encounters ended. The bushwhackers met a Union captain who was forming a company of black troops. The captain, who boasted openly about what his men would do to the Rebels, was summarily killed by Quantrill’s cohorts.

In one exaggerated tale spun by McCorkle, the guerrillas supposedly stopped at a private residence for breakfast. After the group dined with the family, McCorkle claimed that the host’s two daughters sensed the guerrillas’ Southern sympathies despite their blue uniforms. Upon leaving the house, he said, the two girls approached the guerrillas and said, “Gentlemen, from your manners we take you to be Southern men, and while I do not know who you are, if you are Southern soldiers I wish you all the happiness and success that could possibly come to anyone, but if you are Federals, my heartfelt wish is that you all will be in hell before night.” McCorkle said the men let out a cheer, but were sternly silenced by their commander for losing their 4th Missouri Cavalry persona. It is probable that the years added hyperbole to McCorkle’s memory, for it is unlikely that a Kentucky belle living in the war-torn state would make such a rash statement to blue-clad troopers. A handful of Kentucky women had already been jailed for revealing their Southern leanings.

As Quantrill’s raiders maneuvered into central Kentucky, their guise continued to deceive Federal troops. A Union dispatch related that on January 22 the bushwhackers had arrived in Hartford. Telling Union authorities that they were the 4th Missouri Cavalry “detached to hunt guerrillas,” Quantrill requested “a guide to conduct him toward the Ohio River, where the guerrillas most abound.” A Federal lieutenant named Barnett, “who was in the neighborhood as a recruiting officer of the One hundred and twenty-fifth Colored Infantry,” an Indiana trooper named W.B. Lawton, and W. Lownsley of the 3rd Kentucky Cavalry all volunteered to show “Captain Clarke” the way. The dispatch continued: “About three miles from Hartford, near the Hawesville road, they hung Lownsley, it is supposed. He was found in the woods near a week afterward. They shot Lawton after traveling with him about twelve miles, and shot Barnett about sixteen miles from here. Their bodies were all found.”

Following the murders, the guerrillas made their way to Hustonville. Eyeing some fresh horses, the band prepared to make off with several of them. As guerrilla Allen Parmer pulled himself onto one of the animals, the Federal lieutenant who owned the horse rushed out. Pointing at Parmer, the lieutenant said the horses would be taken “over his dead body.” Parmer growled, “That is a damned easy job,” pulled his pistol and shot the lieutenant in the face. The bullet traveled through the lieutenant’s head and broke his neck, killing him instantly. Hurrying from town, the bushwhackers turned their horses toward Danville, the geographic center of Kentucky.

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