It wasn’t long, however, before Gratton Dalton began looking for an easier way to make a living. He lost his job as a Deputy Marshal in 1890, being suspected for cattle rustling, and formed his gang. Its first members were his brother Bob Dalton, Charley Pierce, George “Bittercreek” Newcomb, Charlie “Blackface” Bryant, and Richard L. “Dick” Broadwell. Emmett Dalton would later join also. Newcomb and Pierce would later be members of the much more successful Doolin Dalton gang, formed and led by Bill Doolin and Dalton brother Bill Dalton. In February, 1891, the gang robbed a train in Alila, California, and were pursued by a posse. Their younger brother Bill Dalton, previously a member of the California Legislature, assisted in that robbery. During that robbery, they could not get the safe on the train open, and instead robbed the passengers. Pursued by a posse, Grat and Bill Dalton were captured, while the others escaped. Those who had escaped decided it was best to head into Oklahoma Territory. Once back in Oklahoma they robbed yet another train, and immediately afterward gang member Charlie Bryant became violently ill. Bryant was taken to a doctor in Hennessey, Oklahoma, then left to return to the gang when he was well. Deputy US Marshal Ed Short saw Bryant brought in, and recognized him. He went into the doctors office, but found that the others had departed. Deputy Marshal Short arrested Bryant, but there being no jail in Hennessey, and Short figuring that the rest of the gang would return, he took Bryant by train to Wichita, Kansas. While en route, Deputy Marshal Short gave an extra pistol to a railroad employee. While Short was on the train platform to make certain the Dalton Gang were not pursuing, the railroad worker sat his pistol down to drink water. Charlie Bryant grabbed it, and in the ensuing shootout with Deputy Marshal Short, both Bryant and Short were killed. Charlie Bryant became the first member of the gang to die.

Gratton Dalton managed to escape from jail in September 1891, and returned to once again lead the gang. By that time, the gang had robbed two trains in his absence. The gang went on a semi-successful train robbing spree that lasted until their last train robbery on July 14, 1892. Grat Dalton had by then decided that train robbery was not producing, therefore he wished to turn the gang to bank robbery. Gratton Dalton devised a plan, for whatever reasons, to rob two banks at the same time, in the same town. Not only did Dalton choose to rob two banks simultaneously, a risky move at best, but he also chose to commit the robberies in the Dalton’s hometown of Coffeyville, Kansas. By that time, by later accounts from Emmett Dalton, Deputy US Marshal Heck Thomas was on the trail of the Dalton Gang. His relentless pursuit had pushed them to make one large score, then lie low for a time. Grat Dalton thought Coffeyville would be an excellent opportunity for that score. For reasons unknown, Grat Dalton dismissed gang members “Bittercreek” Newcomb and Charley Pierce, telling them their services were no longer needed. It would prove to be a blessing in disguise for Pierce and Newcomb.

The robbery attempts would be a colossal mistake. On October 5, 1892, the gang entered Coffeyville, simply riding in, then splitting into two teams. The brothers were recognized as soon as they rode into town. They entered the two banks in two separate teams, intent on having only so much time to finish the robberies and flee. By the time they were ready to make their escape, the townspeople had armed themselves and set up to cover all escape routes from the town. A fierce shootout erupted, and by the time it was over, gang members Grat Dalton, Bob Dalton, Dick Broadwell, alias “Texas Jack” Moore, and Bill Power, alias Joseph Evans, were dead, and Emmett Dalton had been shot 23 times, but would survive. Four townspeople, Town Marshal Charles T. Connelly, bank clerk Lucius M. Baldwin, cobbler Charles J. Brown, and merchant George W. Cubine were dead. Bank cashier Thomas G. Ayers was shot in the groin; although seriously wounded, he survived, while townspeople T.A. Reynolds and Louis Dietz were wounded, but not seriously. The gun-battle ended the Dalton Gang. Their outlaw career would prove to have been short and ultimately non productive. However, the legend of the gang and the notoriety they received due to the Coffeyville shootout made them famous. That fame helped drive their brother Bill Dalton in efforts to become more famous than his brothers, and helped spawn the Doolin Dalton Gang, with Bill Dalton, Bill Doolin, “Bittercreek” Newcomb, and Charley Pierce all having their start with the Dalton Gang.