The plan played out to perfection on the night of September 15. The train had just taken on water and was pulling out of the Lelietta station when two men appeared in the cab brandishing Winchesters. After hurriedly halting the steaming train, the engineer and fireman immediately hoisted their hands.
Recalling the robbery decades later, Emmett still harbored an amusing resentment that the fireman had yelled, “The Daltons!”: “So it always was. The Daltons were always blamed even before anyone knew whether they really were the ones at the bottom or not. The fireman had never seen them and had he known them personally he had not had time to recognize Bob. But it was a robbery and the Daltons were to blame.” Then Emmett conceded, “But this time he was right.”
Four bandits stood outside to make sure no passengers made a run for it while the train crewmen were marched through to the express car. The company messenger, perhaps a family man, offered no resistance. The contents of at least one of the two safes were turned over.
The Indian Chieftain was to report in its September 17 edition, “The train was not detained but a short time and very few persons knew what had happened.” It added, “Two blood hounds were brought up from Atoka yesterday morning and an organized pursuit is being conducted.” A day later, the Fort Smith Elevator informed readers, “So quietly did they do the job that passengers did not know the train had been robbed until after they pulled out and were nearly to Wagoner.”
Just as they had hoped to do, the members of the Dalton Gang vanished into the night, with perhaps even their horses feeling proud of themselves.
A last scene of the raid that Emmett remembered was that one of the porters and another man had gotten off the train to see what the commotion was about, but both tried to climb back aboard after Bill Power fired several shots: “There was not enough room for two [on the stairs] and the fat man fell backward to the ground. Just then the train began to move and I could see him crawling on his hands and knees in the same direction the car was going as though he was trying to race the car. However, he got to his feet and managed to swing aboard the last car as it passed. He was angrily shaking his fist at us as the train was swallowed up by the night.”
The good news for the gang was that this robbery resulted in their most profitable take yet, a shade over $19,000. But it seems that as a result of such success, the members began to argue over money. Bob doled out over $3,000 to each man, including his younger brother. One would think they would be happy enough with this payout given their previous shares. But the boys must have anticipated higher expenses during the time between robberies.*
And maybe it was also a lifestyle issue: Bill Doolin, especially, though no monk himself, complained that Bob was throwing away too much money on gambling and women—presumably, ones in addition to the plucky Eugenia Moore. With Bob not promising to mend his profligate ways and that any extra money he kept was for the still-imprisoned Grat Dalton, a disgruntled Doolin quit the gang. Bitter Creek Newcomb and Charley Pierce followed him out the hideout door.
Doolin was not done with the gang for good, but as it was the first time he challenged its leadership, it’s worth knowing more about the man who would come close to surpassing the Daltons as outlaws.
William Doolin was born in 1858 to Michael and Artemina Doolin. His father, a sharecropper who was known as Mack, had been a widower with four children from that marriage when he wed his second wife and had son William and daughter Tennessee with Artemina.
Mack Doolin was able to buy a forty-acre farm on the Big Piney River in Arkansas, and that was where his two youngest children grew up. During the Civil War, John Doolin, an older half brother of Bill’s, enlisted in the Union army but soon kept trying to get out of it. He was finally sentenced to prison at Fort Smith, from which he escaped. By the time he felt it safe enough to return to the family farm, Mack Doolin had died. John took over and managed to avoid the notice of the law.
Bill Doolin grew up to be a tall man for the time at six feet, two inches. He was slender, and according to the biographer Bailey Hanes, he had “thick, unruly auburn hair above a high forehead. Penetrating pale-blue eyes, thin lips, and canine teeth were his trademark. And his nose was long and thin, with a pronounced hook at the end. He always wore a ragged brindled mustache that practically covered his straight mouth.”
He was twenty-three when he left the farm, aiming west. After several itinerant jobs, Bill was hired by Oscar Halsell, who was from Texas and was establishing a new ranch in the Cowboy Flats area of Logan County, Oklahoma. Doolin worked there, and at times for nearby outfits, for the next decade. Among the other ranch hands who worked with him were Bitter Creek Newcomb, Dick Broadwell, Bill Power, and Emmett Dalton.
Doolin was not much of a go-to-town-and-get-rowdy sort of hand, so it was surprising that his trouble with the law began with beer. It was the Fourth of July, and he uncharacteristically decided to accompany several cowboys from the Bar X Bar Ranch across the state border into Coffeyville. Finding the holiday celebrations a tad understated, Doolin and the others appropriated several ash barrels, sawed them in two, and filled them with ice and bottles of beer. In case that would not be enough, they purchased two kegs of cold beer. Apparently, one could buy beer but not drink it there, so being careful, they put all the beer in a wagon and drove it out to a shady grove outside Coffeyville, inviting people to follow them for a drink.
Unfortunately for them, two deputy sheriffs could not leave well enough alone on that Independence Day. Perhaps there had been too many citizens wandering out of town and returning drunk. The two lawmen went out to the sudden saloon the ranch hands had created and asked who the beer belonged to. Doolin replied, “The beer doesn’t belong to anybody. It’s free, help yourselves.”
Such generosity was not appreciated. The deputies said that because Kansas was a dry state, they would have to seize the suds. As one deputy began to roll a keg of beer away, someone fired a shot. There were more shots, and both deputies fell wounded. Doolin took off and kept going, eventually throwing in with the Dalton brothers.
Because the proceeds of the Lelietta train robbery were, after all, at least pretty good and probably because of the infighting and no doubt because of lawmen being more on the lookout than ever before, the Dalton Gang did not strike again until months later. But when they did, it was a doozy. And by then, the outlaw group had expanded to include a free and vengeful Grat Dalton.