Bob and Emmett fled California with a posse on their tail; however; Grat and Bill were arrested. Bob and Emmett made their way back to Indian Territory and hooked up with Emmett’s old ranching buddies Charlie Bryant and Bitter Creek Newcomb. In May 1891, the four robbed the train at Wharton, Indian Territory making off with $1,745. Meanwhile, in California, Grat Dalton was found guilty of the train robbery on July 3, 1891, and was sentenced to twenty years in prison.
Three months after the Wharton robbery in August 1891, Charlie Bryant became ill and was taken to the doctor in Hennessey, Oklahoma Territory. While there, Deputy Marshal Ed Short arrested Bryant while he was recovering from his illness at a local hotel. There being no jail in Hennessey, the marshal loaded Bryant on a train and headed to the federal jail in Wichita. In route, Bryant somehow obtained a gun and attempted to escape. In the ensuing shoot-out between Bryant and Short, both men were killed by shots from the other.
The Dalton Gang’s next robbery was the Katy train at Leliaetta, near Wagoner in Indian Territory. With Bob and Emmett, were Bitter Creek Newcomb, Bill Power, Dick Broadwell, Charlie Pierce, and Bill Doolin. On the night of September 15, 1891, they stopped and boarded the MK&T train, and robbed the express car of $2,500.
Back in California, on September 18, Grat escaped while on the train transferring him to prison. According to one account, Grat was handcuffed to one of two deputies that accompanied him. While one of the deputies was asleep and the other busy talking to other passengers, Grat stole the key to the handcuffs and jumped from the window of the moving train, landing in the San Joaquin River. Grat made his way back to Oklahoma, and quickly joined back up with the gang, while his brother Bill was still in California awaiting trial.
Meanwhile, back in California, Bill Dalton was acquitted on October 10, 1891, for the train robbery that Grat had been sentenced to twenty years for.
The winter of 1891 found the Dalton brothers relatively quiet, but as soon as spring arrived they teamed up with Pierce, Newcomb, Power, Broadwell, and Doolin to plan another train holdup.
Waiting for the at the train at the station on June 1, 1892, at Red Rock in Oklahoma Territory, they sensed danger when the train arrived without any lights shining from its coach windows. Quickly, they abandoned their plans and allowed the train to pass without incident. However, within a short time a second train came along, and this one, they boarded.
Charlie Bryant and Dick Broadwell held the engineer and fireman in the locomotive while Bob, Emmett, and Bill Power walked through the passenger cars taking jewelry and cash. Bill Doolin and Grat Dalton took on the express car, throwing the safe out of the train. Loot in hand, the bandits rode away, only to discover they had gained little for their efforts, as the safe only contained about $50.
Later, they found out that their suspicions were correct regarding the train that they had allowed to pass as it had been full of armed guards protecting $70,000 of the Sac and Fox annuity.
Obviously not happy with their take in June, they planned another train heist on July 14, 1892, at Pryor Creek in Indian Territory. Arriving at the train station they first took what they could find from the express and baggage rooms, then calmly sat down waiting for the train to arrive with their shotguns over their knees. Once again the train was loaded with deputies, but for some reason, they were all at the back of the train. The gang backed a wagon up to the express car and unloaded all of the contents, easily subduing the one armed guard in the express car. When the marshals finally discovered the robbery, a fierce gun battle broke out where two guards were killed, as well as an innocent bystander and another wounded. The gang escaped unharmed making off with $17,000 in cash. After this train robbery, a prize of $5,000 was placed on each of the Daltons’ heads.
With the law hot on their tails, the Dalton Gang split up for a short time. But, it wasn’t long before they began to plan another robbery – this one to be their biggest yet.
In early October 1892, brothers Bob, Grat and Emmett Dalton, along with Bill Power and Dick Broadwell set out towards Coffeyville, Kansas. Arriving on the evening of October 4th at the P.L. Davis farm four miles west of Coffeyville, they made camp for the night and prepared for the next day.
Early on the morning of October 5, 1892, the five outlaws rode into Coffeyville shortly after 9:00 a.m. to find the city’s streets filled with people. Tying their horses in an alley across from the banks, they dismounted and marched down the alley, three in front and two in the rear. The outlaws, disguised with false beards, divided into two groups, with Grat, Power, and Broadwell entering the C.M. Condon & Co. Bank, and Bob and Emmett crossing the plaza to enter the First National Bank.
Disguise or no, when they left the alley they passed within five feet of a man by the name of Aleck McKenna, who recognized one them as a member of the Dalton family. He watched the men as they entered the bank and when he saw a gun pointed at the cashier’s counter in the Condon Bank, he called out “the bank is being robbed!” The cry was taken up and quickly passed to everyone around the square. Wasting no time, the local townsmen quickly armed themselves with weapons from the hardware store and took up positions to defend the town.
Inside the Condon Bank were C.T. Carpenter, one of the owners; Tom C. Babb, bookkeeper; and Charles M. Ball, cashier. They were quickly taken hostage by the outlaws and ordered to surrender the money. But quick-thinking cashier Ball told them there was a time lock on the vault and that it could not be opened for another 10 minutes. Grat, Power, and Broadwell were fooled into waiting, which gave the townsmen additional time to get themselves armed.
Meanwhile, in the First National Bank, Bob and Emmett captured Thomas G. Ayers, cashier; W.H. Shepard, and B.S. Ayers, the bookkeeper, who they forced to collect the money. The two Dalton brothers at first tried to escape out the front door using the three bankers as a shield. But when the townsmen shot at them anyway, they decided to use the rear door.