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At the conclusion of the Civil War, Jeff Clanton, an Army major from Missouri, persuades the last of the Confederacy's Quantrill's Raiders to give themselves up and pledge their allegiance to the Union. Many of the Raiders are infamous wanted men, including the Younger brothers, Jesse and Frank James, Curley Ringo and "Doc" Butcher, a veteran horse thief. Although Jeff promises that they will be paroled as long as records indicate they were on the Confederacy's payroll, Matthew Fowler, a carpetbagger who runs a powerful detective agency, determines to arrest them for the reward money. While Fowler and Joad, the sheriff of Breckenridge, the Missouri town in which the Raiders are being held, stir up sentiment against the outlaws, Jeff races to issue the allegiance pledge. Before they can say the pledge's last words, one of Fowler's deputies shoots and wounds Bob Younger, prompting Jeff to return fire. Jeff then completes the oath and frees the Raiders. Later, as he is about to return to his home, the now-civilian Jeff is arrested for murdering Fowler's deputy. Fowler claims that Jeff knew he had been mustered when he was issuing the oath and therefore shot his man as a civilian. Jeff is tried by a prejudiced court and sentenced to be hanged the following morning. While Jeff sits in jail that night, however, Fowler's estranged wife Lily pretends to be Jeff's rejected lover and, to spite her husband, distracts the jailer long enough to slip Jeff a gun. Jeff escapes but is pursued by a posse and shot in the leg. Joad eventually catches up to the wounded Jeff, but as he is about to take Jeff prisoner, Doc and Bob surprise the lawman and free Jeff. Doc explains that because Fowler connived to have Jeff's allegiance oath declared illegal and the Raiders are now fugitives, they have all embraced a life of crime. Doc and Bob, who lost the use of his arm after being shot by Fowler's deputy, lead Jeff to Quinto, a town in an lawless area known as Badman's Territory. Jeff is surprised to discover Lily singing in the Quinto saloon, but promises to keep her identity a secret. Jeff, the Younger brothers, the James brothers, Doc and Ringo vow to destroy Fowler by robbing banks and other businesses that are protected by his detectives. As hoped, the raids overwhelm Fowler's operation, but Lily worries that Jeff, with whom she is in love, has become heartless. Jeff denies he has changed, insisting that he only wants to finish the job he started. When Cole Younger, the Raiders' leader, suggests that they blow up a gold-carrying train, Jeff proposes a less violent plan, then tells Lily that he will leave Quinto with her after the robbery. Later, Ringo, who like Bob is infatuated with Lily, becomes jealous when Bob gives her some jewelry and instigates a fight. Jeff and the others stop the brawl, but Ringo, who had eavesdropped on Lily's private conversation with Jeff, exposes her as Fowler's wife. Although Jeff defends Lily and forces Ringo out of Quinto, the other outlaws demand Lily's expulsion. To avoid trouble, Lily arranges to meet up with Jeff in three days, then accompanies him and the gang to the train depot. Unknown to the outlaws, a revenge-hungry Ringo has informed Fowler about Jeff's plan, so when Doc waves the train down, a horde of Fowler's men attack. Lily is wounded in the ensuing gunfight, but afterward, Cole accuses her of setting them up. Bob, Jeff, Lily and Doc flee in a wagon, and after eluding the gang, Bob hides out with Lily while Jeff and Doc steal a passing stagecoach. Before Jeff and Doc can pick up Lily, however, Ringo surprises Bob and delivers Lily to Fowler. Although Jeff, Bob and Doc know that Fowler will be lying in wait for them in Breckenridge, they determine to rescue Lily. That night, after robbing a trading post of guns and dynamite, Bob and Jeff slip into Breckenridge, while Doc waits with the stage on the edge of town. Bob shoots Ringo, then Jeff sneaks into Fowler's rooms, where Lily is being kept. After freeing Lily, Jeff fights with Fowler and manages to push the carpetbagger into the path of Joad's bullet. Doc, having heard the signal--three blasts of dynamite--then races into town to pick up Bob, Lily and Jeff, and the foursome escapes. Later, on the trail, Bob and Doc part ways with Lily and Jeff, who are looking forward to a new life together.