Charlie Goodnight moved into the Keechi Valley with his family in 1857 and, like the other ranchers, admired and depended on the wisdom of the experienced pioneer, Oliver Loving. Loving was among a few others, including Reynolds and Matthews, who had initiated profitable trail drives to northern markets prior to the Civil War.
In 1867, when the situation on the frontier was at its lowest point, suffering from debts and nothing but worthless Confederate currency as well as vicious Kiowa attacks, Goodnight and Loving formed a partnership with a handshake at the old Holland Ranch House at Black Springs (Oran). They agreed to invite the valley's other cattlemen, including One-Armed Wilson, to join them on a cattle drive to Fort Sumner where the army was supposed to be paying gold for beef on the hoof.
During their drive, Loving and One-Armed Wilson were attacked by Comanches on the Pecos. Loving was severely wounded, and the two men took refuge in a cave on the river. Wilson successfully found help, which brought Loving to Fort Sumner to recuperate where he lived for nearly another month. Goodnight saw to it that his body was returned to Texas for burial.