On October 5, 1892, the Dalton Gang was wiped out in a shootout in Coffeyville, Kansas bank holdup. From the article:
"The Dalton Gang is wiped out in Coffeyville, Kansas
On October 5, 1892, the famous Dalton Gang attempts the daring daylight robbery of two Coffeyville, Kansas, banks at the same time. But if the gang members believed the sheer audacity of their plan would bring them success, they were sadly mistaken. Instead, they were nearly all killed by quick-acting townspeople.
For a year and a half, the Dalton Gang had terrorized the state of Oklahoma, mostly concentrating on train holdups. Though the gang had more murders than loot to their credit, they had managed to successfully evade the best efforts of Oklahoma law officers to bring them to justice. Perhaps success bred overconfidence, but whatever their reasons, the gang members decided to try their hand at robbing not just one bank, but at robbing the First National and Condon Banks in their old hometown of Coffeyville at the same time.
After riding quietly into town, the men tied their horses to a fence in an alley near the two banks and split up. Two of the Dalton brothers-Bob and Emmett-headed for the First National, while Grat Dalton led Dick Broadwell and Bill Powers in to the Condon Bank. Unfortunately for the Daltons, someone recognized one of the gang members and began quietly spreading the word that the town banks were being robbed. Thus, while Bob and Emmett were stuffing money into a grain sack, the townspeople ran for their guns and quickly surrounded the two banks. When the Dalton brothers walked out of the bank, a hail of bullets forced them back into the building. Regrouping, they tried to flee out the back door of the bank, but the townspeople were waiting for them there as well.
Meanwhile, in the Condon Bank a brave cashier had managed to delay Grat Dalton, Powers, and Broadwell with the classic claim that the vault was on a time lock and couldn’t be opened. That gave the townspeople enough time to gather force, and suddenly a bullet smashed through the bank window and hit Broadwell in the arm. Quickly scooping up $1,500 in loose cash, the three men bolted out the door and fled down a back alley. But like their friends next door, they were immediately shot and killed, this time by a local livery stable owner and a barber.
When the gun battle was over, the people of Coffeyville had destroyed the Dalton Gang, killing every member except for Emmett Dalton. But their victory was not without a price: the Dalton’s took four townspeople to their graves with them. After recovering from serious wounds, Emmett was tried and sentenced to life in prison. After 14 years he won parole, and he eventually leveraged his cachet as a former Wild West bandit into a position as a screenwriter in Hollywood. Several years after moving to California, he died at the age of 66 in 1937."