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Born in 1853 in Rock Island, Illinois, not much is known of his early life.When he moved out west he gained the reputation of gunfighter and outlaw. He was reported being in Dodge City, Kansas where he met, and became friends with, Wyatt Earp and Doc Holiday. After moving to Texas in 1878 he became a Texas Ranger, and there he met Curly Bill Brocius. His position as a Texas Ranger came to an end that spring as rumors spread that he had helped Curly Bill escape from jail. He and Curly Bill moved to Arizona and soon after joined up with the Clantons.

In 1882 McMasters was hired by Wyatt Earp to help track down Curly Bill. Shortly after the killing of Morgan and the attempt on Virgil's life, McMasters became another member of the posse that participated in the Vendetta Ride. Stories vary about his death but the most reasonable accounts say he died in Colorado in 1892.