In Oklahoma, after the Civil War, conflict between homesteaders and cowboys leads to the formation of outlaw gangs like the James Boys and the Younger Brothers. After U. S. Marshals target the Dalton gang and attack them during a bank robbery, the only member remaining alive is Bill Doolin. Later, in self-defense, Doolin kills Wichita, the man who informed on the Daltons, and is chased by a posse. Doolin evades his pursuers, however, and joins forces with Red Buck, Arkansas Tom Jones, Tulsa Jack Blake, Bitter Creek and Little Bill, who become known as the Doolin Gang. After several months of robbing banks, Doolin splits the take among the gang members and orders them to separate until things cool off. They agree to meet in three months time in the town of Ingalls. Riding just ahead of the pursuing marshals, Doolin hides out in a church in the small town of Claymore. After completing a service, Deacon Burton invites Doolin to join his family for dinner. At first, Doolin turns down the invitation, but when the posse returns, he accepts in order to avoid it. At dinner, he talks with Elaine, Burton's attractive daughter, who speaks so tenderly of the joys of farming that Doolin decides to try it. By the end of the three months, Doolin, using the name Daley, has married Elaine and settled on a farm. When Little Bill returns for him, he explains that he wants to leave the gang. Later, however, two gang members, posing as marshals, reveal Doolin's identity to Elaine, and Burton persuades him to leave town. As time passes, the gang grows increasingly restive. Doolin takes them back to Ingalls for a rest, but an undercover marshal is waiting in town, and fetches the posse. During the ensuing gunfight, Tulsa is killed and Arkansas is captured. Later, Bitter Creek and Red Buck are also killed. Doolin then suggests that he and Little Bill hide out on Doolin's old farm, which he is sure will be deserted. To his surprise, Elaine is still living there, waiting for his return. They decide to leave together for an area between Kansas and Texas that has not been claimed by the government. When the marshal in Claymore sees Elaine buying supplies, he becomes suspicious and investigates. Little Bill warns Doolin and then starts a stampede of wild horses to cover Doolin's escape. Little Bill is killed in the stampede, but Doolin manages to slip into town and meet Elaine. As they talk, he realizes how hard a life on the run will be for her and sends her to her parents. After she rides out of sight, Doolin walks out to meet his death.