The Dalton brothers were part of a large family headed by parents Adaline Younger Dalton and James Lewis Dalton. Lewis Dalton came west from Kentucky to Missouri during the late 1840s and in the 1850s, he was trading horses and running a saloon in Westport, Missouri (now Kansas City) when he married Adeline. Adeline’s brother was the father of Bob Younger, Cole Younger and James Younger.
Most of their 15 children were born in Missouri before the family migrated to Indian Territory (now Oklahoma) in 1882.
In 1886, they moved again to a place near Coffeyville, Kansas. In this rough and wild area, the Dalton brothers inherited a tradition of violence on the bloody ground of the Missouri-Kansas border, where Quantrill’s Raiders and other guerilla bands operated before and during the Civil War.
When the Oklahoma Territory opened for settlement in 1889, the family headed south again. However, Lewis died along the way leaving Adaline to raise the younger children alone. Adaline continued on, placing a claim on the banks of Kingfisher Creek in Indian Territory, where initially, she and the family lived in a dugout. By this time the older Dalton brothers were on their own.
For a short time, the brothers served on the side of the law, working as U.S. Deputy Marshals. Their older brother, Frank Dalton, was commissioned a Deputy Marshal for the federal court in Fort Smith, Arkansas and Bob Dalton served on several of his posses. On November 27, 1887, in a gun battle with the Smith-Dixon Gang, Frank Dalton was shot and killed in the line of duty.
Grat Dalton followed in Frank’s footsteps, first taking his place as a Deputy Marshal in Fort Smith, Arkansas and two years later as a Deputy Marshal for the Muskogee court in Indian Territory in 1889. That same year he received a bullet in his arm while attempting to arrest a suspect. Bob Dalton was also commissioned as a Deputy Marshal for the federal court in Wichita, Kansas, working in the Osage Nation, in 1889.
Bob Dalton, who would later become the leader of the Dalton Gang, was the wildest of the bunch. When he was just 19, he killed a man, claiming it was in the line of duty. Nevertheless, some suspected that the victim had tried to take away Bob’s girl.
While Emmett Dalton worked as a member of some of his brothers’ posses, he made his living working as a cowboy on the Bar X Bar Ranch near the Pawnee Agency in the present-day Osage Nation. While working at the ranch, Emmett met two men who would later become members of the gang — Bill Doolin and William St. Power, alias Bill Power. Power, also known as Tom Evans, who had drifted into the area from Texas with a trail herd from the Pecos.
Emmett also made the acquaintance of several other cowboys working on nearby ranches who would later become part of the gang. These included Charlie Pierce, George “Bitter Creek” Newcomb, Bill EcElhanie, Charlie Bryant, and Richard “Dick” Broadwell, alias Texas Jack, alias John Moore.
Charlie Pierce was from the Blue River country in Missouri but headed to Indian Territory to avoid serving jail time for whiskey peddling.
Dick Broadwell was from a prominent family near Hutchinson, Kansas and at the opening of Oklahoma Territory, he staked a claim to a homestead in the Cowboy Flats area. There, he met and a young lady who owned the homestead next to his and asked her to marry him. After their marriage, she persuaded him to sell both claims and move with her to Fort Worth, Texas, where she disappeared with their money. The embittered Broadwell returned to Indian Territory and started work on the ranches.
George Newcomb, who was known as “Bitter Creek” Newcomb, was originally from Fort Scott, Kansas. Starting his career as a cowboy at the age of 12, he worked for C. C. Slaughter on the Long S Ranch in Texas before drifting into Indian Territory.
Charlie Bryant came from Wise County, Texas. He had a gunpowder burn on his cheek that earned him his nickname “Black-Faced Charlie.”
For a short time, the Dalton brothers served with distinction on the side of the law. But, a narrow margin separated the lawless from the law enforcers during those rough times. Slipping from one side to the other, Bob Dalton, along with his brother Emmett, were charged with selling whiskey in the Osage Nation on March 21, 1890.
Jumping bail, Bob and Emmett headed to New Mexico. Forming their first “gang”, Bob recruited George “Bitter Creek” Newcomb, Bill EcElhanie, and “Blackfaced Charlie” Bryant to ride with them. It was at a gambling house in Silver City, New Mexico that the Dalton Gang committed their first robbery.
After riding into the mining camp, the crew sat down at a faro game, where they lost heavily. Convinced the game was crooked, they pulled their guns, taking back what they had lost and then some. Bob and Emmett fled to California, where their younger brother Bill was a successful farmer and rancher.
In September 1890, Grat was arrested for stealing horses but was later released for lack of evidence. Grat lost his job as a Deputy Marshal for conduct unbecoming an officer, but he still worked as a posse man for other deputy marshals in the area for a time. Later, he too, left Indian Territory, joining his brothers in California.
Before Bob, Emmett, and Grat arrived at Bill’s ranch in California, Bill had married, was living a respectable life, and had become involved in politics as part of the Populist Party. As a member of the party, Bill became embroiled in a Populist fight with the railroad backed political machine, referring to the railroad as the S.P. Robber Barons. This political fight was based on battles between the Southern Pacific Railroad and local farmers over land disputes.
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.