On April 1, 1862, Ferguson encountered 16-year-old Fount Zachery in Fentress County. Zachery was carrying a shotgun. He surrendered the weapon, but Ferguson shot him anyway. Almost as soon as Zachery hit the ground, Ferguson was on him with his Bowie knife, and Fount Zachery became the first of four Zachery males to fall to Ferguson. Ferguson justified his actions by claiming he had official orders to kill any armed man in the area.
Over the next few weeks, Ferguson’s men killed their leader’s cousin Alexander Huff in Fentress County; Union guerrilla Elijah Kogier in Clinton County, whom they shot down as his young daughter clung to him; and Fount Zachery’s grandfather James. James Zachery’s daughter Esther would testify that she saw Ferguson chasing her father through the family orchard, yelling to his men, ‘Shoot him, damn him, shoot him!’
Toward the end of April, Colonel John Hunt Morgan’s Kentucky cavalry passed through Sparta, Tennessee, and Ferguson and some of his men joined the force to serve as scouts. Morgan’s men crowded around Ferguson, eager to get a glimpse of the notorious outlaw whose exploits were already becoming legend in the region. Ferguson and several of his guerrillas rode with Morgan on some raids, fighting at Tomkinsville, Lebanon, and Cynthiana, Kentucky, and on June 21 at Gallatin, Tennessee.
Ferguson became well acquainted with Morgan’s second in command and brother-in-law, Major Basil W. Duke. Duke warned his infamous scout that there would be no abusing of prisoners. Ferguson was indignant. He assured Duke he would never harm regularly commissioned officers captured in combat, because he had nothing personally against them ‘except that they are wrong, and oughtn’t to come down here and fight our people.’ He admitted, though, that if he came across any ‘hounds’ he had just reasons to kill, he would not hesitate to kill them.
By the fall of 1862, Ferguson had focused himself almost exclusively on personal vendettas. In October, he killed a man named Wash Tabor, whom he suspected of ambushing and killing three of his men. Ferguson did not harm others captured along with Tabor. He explained to prisoner George Thrasher, ‘I’m not in favor of killing you, Thrasher, you have never been bushwhacking or stealing horses. I have killed old Wash Tabor, a damned good Christian, and I don’t reckon he minds dying.’ On a later occasion, the mother of one of Ferguson’s prisoners, John Crabtree, begged for her son’s life, but the guerrilla leader told her that her concern was too late in coming. The time to worry was years ago, he suggested, when she still had the chance to raise her son right.
Several of Ferguson’s victims belonged to the 7th Tennessee Infantry (Union). So it is not surprising that the commander of that regiment, Colonel William Clift, was eager to attack the independent Rebel bands trolling the Tennessee-Kentucky border. ‘I deem it highly indispensable to break up these guerrilla companies as speedily as possible, as there can be no safety to the peace of the country while they are permitted to exist,’ he said.
On December 15, Union XIV Corps commander Major General William Rosecrans issued an order allowing Major General George H. Thomas, commander of the center of the XIV Corps, to send Colonel Frank Wolford’s 1st Kentucky Cavalry after Ferguson and another Tennessee guerrilla, Oliver Hamilton of Overton County. ‘Colonel Wolford has permission to pursue and capture Hamilton and Ferguson,’ Rosecrans wrote, ‘but let him be careful not to get caught himself.’ Nothing came of Wolford’s ambitions to snare the guerrilla chief.
On New Year’s Night 1863, Ferguson set out to rid himself of some of his most troublesome enemies in Kentucky. The first to fall was Union guerrilla Elam Huddleston. After an hour-long gunfight between Confederate guerrillas and the Huddleston brothers Elam and Moses, aided by their cousin David Huddleston, Ferguson killed his intended victim at his house. Next to die were the Zachery brothers Peter and Allen, sons of James Zachery. Ferguson killed Peter with his knife after a fierce hand-to-hand struggle.