He and Jim were involved in a gunfight with the law near Monegaw Springs, Missouri. John lost his life March 16, 1874. Cole joined the destructive William Clarke Quantrill in 1861, his brother Jim joining a couple of years later at the Civil War's end. At first Cole was made a lieutenant of cavalry in Quantrill's band in 1862, taking part in the Battle of Lone Jack. When the raid of Lawrence was made, Captain Cole Younger rode with the men.
War plays strange things with a man's mind.
Men returned home from the War disillusioned, broken, hurting, beaten inside and out. Thinking of revenge against the Yankees was only natural for them. It was the Yankees who had stolen their families, their houses, everything they owned. Some of the soldiers took up the life of the outlaw having been issued guns, taught to kill, trying to take back a piece of their lives that had been taken. Quantrill and his lieutenant 'Bloody' Bill Anderson had taken these country boys and made them experts in riding and marksmanship, drilling them in the art of guerrilla warfare.