I guess it would be popular or romantic to say that the Dalton brothers were driven to a life of crime—the fact is they grew up during wild times in a wild place. They were raised on the border of Indian Territory, near Coffeyville, Kansas.

For a short time they served on the side of the law, working as deputy marshals. Their older brother, Frank Dalton, was commissioned a deputy marshal for the federal court in Fort Smith, Arkansas. On 27 November, 1887 in a gun battle with the Smith-Dixon Gang, Frank Dalton was shot and killed.

Grat Dalton, who had moved to California along with their brother Bill, returned to Indian Territory, and took up where his brother had left off. Working as a deputy he received a bullet wound in the arm while attempting to arrest one suspect, and in 1889 he was commissioned a deputy marshal for the Muskogee court.

Bob Dalton was a deputy marshal for the federal court in Kansas in Wichita, working out in the Osage Nation. He also served on several of his brother Frank's posses.

Emmett Dalton also worked as member of some of his brother's posses, but for the most part he earned a living as a cowboy working on the Bar X Bar Ranch near the Pawnee Agency. It was on the ranch that Emmett would meet two of the future gang's members, Bill Doolin and William St. Power, alias Bill Powers, alias Tom Evans.

Not much is known about Bill Power other than he drifted in to the Territories from Texas with a trail herd from the Pecos.

While working at the Bar X Bar, Emmett also became acquainted with cowboys and future gang members working on the ranches nearby. They were Charlie Pierce, George Newcomb, Charlie Bryant, and Richard (Dick) Broadwell, alias Texas Jack, alias John Moore.

Dick Broadwell came from a prominent family near Hutchinson, Kansas. At the opening of Oklahoma Territory he staked a claim to a homestead in the Cowboy Flats area. He met and fell in love with the young lady who owned the homestead next to his and asked her to marry him. She agreed and persuaded him to sell both claims and move with her to Fort Worth, Texas, where she disappeared with the money. He returned to the Territories and started work on the ranches.

Charlie Pierce hailed from the Blue River country in Missouri. He fled to the Indian Nation to avoid trouble in Missouri and settled in the Pawnee country. He spent time in the Fort Smith jail for whiskey peddling.

George Newcomb, known as Bitter Creek Newcomb, came from Fort Scott, Kansas. At the age of twelve Newcomb started his career as a cowboy working for C. C. Slaughter on the Long S Ranch in Texas. He later drifted into the Territories.

Charlie Bryant came from Wise County, Texas. He had a black mark on his cheek from a powder burn that earned him his nickname Black-Faced Charlie.

While serving as head of the Osage police, Bob Dalton was accused of selling whiskey. Grat Dalton also got into trouble about the same time and was dismissed as deputy marshal for conduct unbecoming an officer. Although they were not deputy marshals they still worked as posse men for other deputy marshals. However, pay was slow in coming.

Then in July of 1890, Bob, Grat, and Emmett were accused of stealing horses near Claremore, Indian Territories and selling them in Kansas. With a posse hot on their trail, Bob and Emmett left the Territories for California. Brother Grat was arrested and placed in jail. He was later released for lack of evidence. He too would leave the Territories and go to California to join his brothers.

In California the boys would join their brother Bill and events would soon have them fleeing the law again. On the night of 6 February, 1891, the Southern Pacific Rail Road train was robbed at Alila, California. The Dalton boys were accused. Once again Bob and Emmett were fleeing the state with a posse after them. Grat and Bill was arrested.

Bob and Emmett made their way back to the Territories, but the law was after them and making things hot for the boys. While hiding out in the Indian Nations the boys hooked up with Emmett's old ranching buddies Charlie Bryant and Bitter Creek Newcomb to rob the train at Wharton, Oklahoma Territory, in May of 1891. The gang made off with $1,745 of the railroad's money.

Shortly after the Wharton robbery, Charlie Bryant became ill and was taken to the doctor in Hennessey, Oklahoma Territory. Deputy Marshal Ed Short saw Bryant when he was brought into town and arrested him in the hotel as he was recovering from his illness. There was no jail in Hennessey so the marshal took his prisoner by train to the federal jail in Wichita. During the trip Bryant made a desperate attempt to escape. He secured a pistol and in a blazing shoot-out with the marshal both men died from shots received from the other.

The gang's next robbery was the Katy train at Leliaetta, near Wagoner, Indian Territory. With Bob and Emmett were Bitter Creek Newcomb, Bill Powers, Dick Broadwell, Charlie Pierce, and Bill Doolin. On the night of 15 September, 1891, they stopped and boarded the train, and robbed the express car of $2,500.

Meanwhile in California, on 3 July, 1891, a jury found Grat Dalton guilty of the Alila train robbery. While awaiting sentence, Grat escaped from jail on 18 September and made his way back to Oklahoma. He promptly joined up with his brothers.

At the end of May in 1892 the three Dalton boys teamed up with Pierce, Newcomb, Powers, Broadwell, and Doolin for another train holdup. On 1 June, 1892, at the train station at Red Rock, they positioned themselves and awaited the approaching train. When the train entered the station the train coaches were dark. The gang sensing something was wrong were allowed to leave the station unmolested. Suddenly a second train appeared and as it stopped at the station the gang boarded it and proceeded to rob it. As it turned out the gang was correct in their suspicion, the first train was full of armed guards protecting $70,000 of the Sac and Fox annuity. Unfortunately the second train had little of value on it and the gang only made off with $50.

On 14 July, 1892, the gang made its last train robbery at Adair Indian Territory. Once again the train was loaded with deputies, but the gang was so quick and quiet with their work that the marshals didn't realized the train was being robbed until the job was almost completed. Unloading from the train the marshals engaged in a fierce but brief gun battle with the bandits. During the battle an innocent bystander was killed and another one wounded. The bandits would escape unharmed with an undisclosed amount of cash.

After the Adair robbery the gang split up and went their own ways. With the law on their trail, the Dalton boys figured to make one last robbery and get enough money to leave the country. A plan was devised to rob two banks in the same town at the same time, thus getting enough money to leave the country, and also go down in history by accomplishing something that no other outlaw gang had ever attempted. The perfect town for the robbery was Coffeyville, Kansas, the Dalton boys' old home town.

Early in the morning on 5 October, 1892. five members of the gang, Bob, Grat, Emmett, Bill Power, and Dick Broadwell rode into Coffeyville. They tied their horses in the alley across from the banks, then strolled across the street, divided into two groups, and entered the Condon National Bank and First National Bank. However they were recognized by citizens and the alarm was given. Townsmen quickly armed themselves with weapons from the local hardware stores and took up positions to defend the town. As the bandits tried to make good their escape a fierce gun battle took place in which four citizens and four bandits lost their lives. Emmett, the sole surviving member of the gang, was seriously wounded. He would recover from his wounds and stand trial for the crime. He was sentenced to life in prison, but was later pardoned by the governor, and spent the rest of his days in California.