He made a habit of placing secessionist flags at prominent locations, looking to start fights with pro-Union forces.
In July 1861 it was occupied by pro-Union forces of the Missouri Home Guard.
However, by April 1935 the fragile truce between pro-open shop management and pro-union forces broke.
There had been a number of clashes in the Charleston and Bird's Point area for the previous week between pro-Union forces and secession groups.
In such a situation, the pro-union forces may win the immediate battle, but they would lose the wider fight for a democratic Britain.
Much of the subsequent actions taken in 1861 were skirmishes between pro-Union and pro-Confederacy irregular forces in border states like Missouri and Kentucky.
Although sympathetic to secession, he sought to retain neutrality for Kentucky for the conflict, until pro-Union forces compelled him to resign from the governorship.
Elected to the Kentucky Senate in 1861 he became the leader of the pro-Union forces.
During the American Civil War, many of the mission's buildings were burned down in warfare between pro-Confederate and pro-Union forces.
The pro-Union forces, who recognized John Ross as chief, held meetings at Cowskin Prairie.