On February 6, 1891, the Dalton Gang attempted their first train robbery near Alila, California. Bob, Emmett, and Grat Dalton were only three of Lewis and Adeleine Dalton's 10 sons. The brothers grew up on a succession of Oklahoma and Kansas homesteads during the post-Civil War period, when the region was awash in violence lingering from the war and notorious outlaw bands like the James-Younger Gang. Still, the majority of the Dalton boys became law-abiding citizens, and one of the older brothers, Frank, served as a deputy U.S. marshal.
Ironically, Frank's position in law enforcement brought his younger brothers into lives of crime. When Oklahoma whiskey runners murdered Frank in 1887, Grat took Frank's place as a deputy marshal and recruited Emmett and Bob as assistants. Disillusioned by the fate of their older law-abiding brother, the three Dalton boys showed little respect for the law and began rustling cattle and horses to supplement their income. The brothers soon began to use their official law enforcement powers for their own ends, and in 1888, they killed a man for pursuing Bob's girlfriend.
By 1890, all three men were discredited as lawmen, though they managed to escape imprisonment. Taking up with some of the same hardcore criminals they had previously sworn to bring to justice, the Daltons decided to expand their criminal operations. Bob and Grat headed to California, leaving Emmett behind in Oklahoma because they felt he was still too young for a life of serious crime. In California, they planned to link up with their brother Bill and become bank and train robbers.
The Dalton Gang's first attempt at train robbery was a fiasco. On February 6, 1891, Bob, Grat, and Bill tried to rob a Southern Pacific train near Alila, California. While Bill kept any passengers from interfering by shooting over their heads, Bob and Grat forced the engineer to show them the location of the cash-carrying express car. When the engineer tried to slip away, one of the brothers shot him in the stomach. Finding the express car on their own, Bob and Grat demanded that the guard inside open the heavy door. The guard refused and began firing down on them from a small spy hole. Frustrated, the brothers finally gave up and rode away.
The Daltons would have done well to heed the ominous signs of that first failed robbery, but instead, they returned to Oklahoma, reunited with young Emmett, and began robbing in earnest. A year later, the gang botched another robbery, boldly attempting to rob two Coffeyville, Kansas, banks at the same time. Townspeople caught them in the act and killed Bob, Grat, and two of their gang members. Emmett was seriously wounded and served 14 years in prison. Of all the criminal Dalton brothers, only Emmett lived into old age. Freed from prison in 1907, he married and settled in Los Angeles, where he built a successful career in real estate and contracting.