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 Cole (composer) booking contract with Michael Levitt. Although Cole was able to avoid the Troubadours’ schemes, in the end, he was not able to avoid the lawsuit against his company from Levitt, who fined Cole and Johnson $1000. Cole’s company faced several trials, including quarrels over finances and transportation; also, the competition of the Black Patti organization was a constant battle. Cole's group succeeded through Bob Cole’s skills in management and his inventiveness in black show business. By 1900, "A Trip to Coontown" finally stopped its production, and the partnership between Cole and Billy Johnson ended due to either Johnson’s alcoholic nature,