Cole Younger the three Youngers (Cole, Bob, and Jim) did not. They and another gang member, Charlie Pitts, waged a gun battle with a local posse in a wooded ravine along the Watonwan River west of Madelia, Minnesota. Pitts was killed, and Cole, Jim, and Bob Younger were badly wounded and captured. Cole, asked about the robbery, responded, "We tried a desperate game and lost. But we are rough men used to rough ways, and we will abide by the consequences." Cole, Jim and Bob pleaded guilty to their crimes to avoid being hanged. They were sentenced to life in prison at
Bob Dalton (outlaw) would join his brothers in California. On the night of February 6, 1891 the Daltons raided a train operated by the Southern Pacific Railroad, near Alila, stealing $60,000. The boys were accused of the crime causing Bob and Emmett to flee the state, with a posse after them, while Grat and Bill were arrested. Grat would be found guilty on July 3, 1891 after a jury trial. Bob and Emmett retreated to the Indian Territories, but the law was still after them, so they decided to hide themselves. When Emmett worked, previously, at the Bar X Bar Ranch he became