The year was 1861 and Jacob Stephens, a seventeen-year-old farm boy from North Carolina, enlisted with the Confederate forces at the outbreak of hostilities between the States; a conflict also known as the United States Civil War.

Following recruitment, he took up arms with the 1st Regiment North Carolina Volunteer Infantry. His ability in handling animals (he excelled with horses) and his skill with both rifle and handgun saw him often chosen to carry out perilous scouting assignments.

The first couple of years saw him spend time scouting, or otherwise engaged in behind the lines clandestine missions. From there Jacob graduated to that of riding with William Quantrill and his band of guerilla fighters. The group who rode under the name of 'Quantrill's Raiders,' to begin with acted within the accepted rules of warfare; but as the conflict continued, those rules fell by the wayside.

Jacob's above-average height of six feet and five inches soon saw him dubbed with the name of 'The High Man,' after a legendary Irish warrior hero. But Jacob's penchant in sending his foes to the Promised Land saw him as something other than a hero by the Northern Union forces. This unfolded in the posting of a sizeable bounty on his head and, alive or dead, it mattered not.

Teaming up with a sixteen-year-old abused river-barge girl, Jacob made his way south along the Santa Fe Trail to dodge his pursuers. Northern guerilla militants, the Red Legs, took a particular interest in him; as they did with anyone who rode with Quantrill.

Throughout their travels, the pair encountered army deserters, river men, outlawed longriders, muleskinners, ex-guerrilla fighters, red Indians and drifters. Many of whom were willing to put a bullet in him to correct the reward money Jacob carried on his head.