The Dalton gang attempts to rob two banks simultaneously in Coffeyville, Kansas, but meets resistance from townspeople, who wind up killing four of the five bandits. Emmett Dalton, the sole survivor, returned to the site of the crime nearly 40 years later and offered a caution to would-be thieves: "The biggest fool on earth is the one who thinks he can beat the law, that crime can be made to pay. It never paid and it never will and that was the one big lesson of the Coffeyville raid."
Grat, Bob, and Emmett Dalton turned to a life of crime when they became bored with their other career possibilities on the Western frontier. They started with cattle rustling and moved on to armed robbery in 1890. Their younger brother, Bill, soon joined their endeavors. On February 6, 1891, Bob, Grat, and Bill tried to rob a Southern Pacific train heading to Los Angeles, California. Despite shooting and wounding a guard, the brothers didn't score any money, and Bill and Grat were captured.
Although Bill managed to escape the charges, Grat received a 20-year sentence. However, he escaped from the train that was taking him to prison, and all the brothers headed back to the Midwest together, where they recruited the best gunmen they could find and began an impressive crime spree. They got $14,000 from a train robbery in Oklahoma and then $19,000 from a bank.
Eugenia Moore, who was engaged to Bob, was in charge of scouting out the best robbery targets for the gang. She was adept at chatting with bankers and railroad workers in order to find out when large sums of money were to be transported. For over a year, the Dalton gang completed a streak of successful robberies that were designed to bring them enough money to retire. However, Eugenia died of cancer, and the gang soon made a huge blunder. Emmett, Grat, Bob, Dick Broadwell, and Bill Power rode into Coffeyville, Kansas, wearing false beards and carrying rifles. As Grat, Broadwell, and Power walked into the Condon Bank and Bob and Emmett entered the First National Bank, one of town's citizens recognized the Daltons and quickly called the town's men to action. (Some sources report that Moore was still alive when the gang went to Coffeyville; others report that there were in fact six robbers that day, not five, and that Moore was the sixth.)
As the gang was about to make their getaway, a throng of armed townsfolk surprised them. The five thieves shot their way to the alley where their horses were waiting and tried to defend themselves, but they were greatly outnumbered. In the epic gunfight that ensued, all five men were shot, but not before killing a number of the makeshift vigilantes, many of whom had been armed for the fight by a local hardware store. Dick Broadwell made it out of the alley on his horse but died a few miles outside of town.
Emmett Dalton, who had been shot more than 20 times, was the only one that managed to survive. He received a life sentence for the murder of the men who tried to stop him but was released a mere 15 years later. He lived a peaceful and law-abiding life until his death in 1937. In 1894, law enforcement officials shot his younger brother Bill, who was not at the fateful Coffeyville robbery, as he tried to escape deputy marshals who were trying to arrest him.