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Silver City, New Mexico Vintage Postcard

Bill’s anger with the railroad is thought to be one of the reasons the brothers decided to rob a Southern Pacific train headed to Los Angeles on February 6, 1891. Prior to this robbery, Bill had not been in trouble with the law at all. Bill, along with Bob, Grat and Emmett attempted to hold up the train at Alila, California, but this first attempt at train robbery was a fiasco. While Bill kept the passengers from interfering by shooting over their heads, the others forced the engineer to show them the location of the cash-carrying express car. When the engineer, a man by the name of George Radcliffe, tried to slip away, he was shot and killed.

Finding the express car on their own, the guard refused to open the heavy door and began firing on them. Thwarted, the brothers finally gave up and rode away.

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 $1745. 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, two deputies, handcuffed to one of them, accompanied Grat. 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.

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