Born in Pineville, Bell County, Kentucky, Wilburn attended local schools and entered the United States Army Infantry when he came of age, serving two enlistments in the 1890s.
He led a National Guard detachment into Virginia on horseback to hunt Frank Ball, who had escaped from the Kentucky penitentiary where he was serving a life sentence.
First working to persuade farmers to join the ATC, the Night Riders received paramilitary training and began to exert harsher power: they whipped disloyal members, murdered opponents, burned buildings and tobacco stores, and temporarily seized entire towns, including three county seats in Kentucky in late 1907 and 1908.
In the spring of 1908, while living in Sturgis, Union County, Kentucky, Wilburn made a series of arrests of Night Rider leaders and protected numerous key informers.
On May 9, 1911 the United States Supreme Court ruled that the American Tobacco Company was in fact an illegal monopoly and violated the Sherman Anti-Trust Act of 1890.