A hail of lead went over Emmett Dalton’s head as his horse spun around like a dog chasing its tail: a rifle bullet found marked him by ricocheting off his right hip, another hit his groin; he was also hit in the right arm, and moments later a shotgun blast made him leap out of the saddle. He fell to the ground a few feet away from where his brother Bob had been shot and left to die. Up to that point Emmett had been the only one of the gang who had not been hit and would have made it out of town if he had not tried to go back to rescue Bob.
His older brother Grat had already been shot dead a couple of yards away along with the other Dalton gang member, Bill Power, in what would be known as “Death Alley.” The moment Emmett watched the life drain from his brother’s eyes, some men with rifles and carbines surrounded them, and at that moment he would have expected to die as well. Surprisingly, although he sustained 23 wounds, Emmett Dalton did not die. He would be the only one of the five members of the Dalton gang to survive the most ill-fated bank robbery in the history of the West.
It had only taken 15 minutes in Coffeyville, Kansas, to end the career of one of the most famous outlaw gangs of the American West of the early 1890s.
Before Coffeyville
Some would say that the Dalton boys were predisposed to a life of crime having grown up in the shadow of Frank and Jesse James and brothers Bob, Cole and Jim Younger. In fact, they were closer to the notorious outlaw gang than anyone else. They were related: their mother, Adeline Younger was the aunt of Cole, Bob and Jim Younger and a cousin of Frank and Jesse.
But although they were related to the most infamous outlaws of the era, living outside the law was not necessarily a reality in the 1880s for the Dalton family, including Bob, Grat and Emmett and older brother Frank, who was a respected deputy sheriff. As young men growing up in Missouri, Oklahoma, and Kansas, the boys had almost never been in serious trouble.Originally from Missouri, the Dalton family had moved over the years, living in Kansas City, Kansas, and then northeastern Oklahoma in 1882. In 1886 they moved to Coffeyville in southeast Kansas. At that time Grat was 25 years old, Bob 17 and Emmett 15. Frank was 2 years older than Grat and worked for Judge Isaac Parker’s court in Ft. Smith (Arkansas).
Unfortunately, less than a year after the family moved to Coffeyville, Frank would be killed, an event that would begin a radical change for the three younger Dalton brothers. Frank was on the trail of a band of outlaws when he was ambushed and killed in a shootout on November 27, 1887.
This prompted Grat to take his brother’s place as deputy sheriff at Ft. Smith. Bob followed suit within a year, taking the badge of deputy sheriff in 1888 and working for the federal court in Wichita, Kansas. Part of his duties included pursuing outlaws, gun runners and smugglers in the Indian Territory of the Osage Nation.
Even their younger brother, Emmett, then a cowboy, was occasionally deputed to ride on Grat or Bob’s estates, so he too had worn a badge before the Dalton boys turned to a life of crime in the 1890s. How they turned away from law enforcement and became outlaws begins and ends with Bob Dalton.
Bob had a wild streak, and wearing the deputy marshal badge at age 19 had made him even bolder. Shortly after becoming sheriff he killed his first man. Bob claimed it was within the limits of his duties, others thought differently, but Dalton remained a deputy sheriff until March 1890, when he was arrested for selling whiskey to members of the Osage Nation the previous Dec. 25.
It cost him his badge, but he was released on bail pending a trial in September. Around the same time, Grat was charged with alleged horse theft. The charges turned out to be unfounded and sketchy, but soon after he was removed from office-Bob and Grat’s careers as law enforcers were over, and their careers as outlaws just beginning.
Bob avoided bail and the two brothers left Indian Territory. They spent a short time in New Mexico, where they took their first shot at a gambling parlor, and then headed to California where another brother, Bill, owned a ranch. Like his brother Frank previously, Bill Dalton had avoided a life of crime. He was married and involved in politics in California, which in the 1890s meant sharp disputes between ranchers, farmers, and the powerful Southern Pacific Railroad.
For whatever reason, Bob and Grat decided to “help” in the cause and convincing Bill and Emmett to join, they attempted to rob a Southern Pacific train bound for Los Angeles on February 6, 1891. It did not go as planned, they ended up shooting and killing the driver and with finding the boxcar locked and no way to force the agent inside to open it.
After a few minutes they ended up fleeing empty-handed with a murder charge on their heads. Bob and Emmett escaped and headed to Oklahoma but Grat and Bill were caught and stood trial. Bill was acquitted, perhaps because of his political connections, but Grat was sentenced to 20 years. He did not serve a single day. He managed to pull off a daring escape from a moving train bound for prison. He returned to Indian Territory in Oklahoma to meet Bob and Emmett.
Return to Indian territory
Bob and Emmett had already formed a small band with some of Emmett’s old cowboy friends. They successfully completed their first train robbery in May 1891. In September they robbed another train and escaped with about $10,000. The Dalton gang hit the railroads again in Jun 1892 along with George “Bitter Creek” Newcomb, Bill Power, Dick Broadwell, Charlie Pierce, and Bill Doolin, who would later split up and form their own gang.
At the time, Bill Doolin, Bob, Grat, and Emmett Dalton were among the most wanted train robbers in the territory.The Dalton and Doolin gangs, which included George Newcomb, “Dynamite Dan” Clifton, William F. “Little Bill” Raidler, and Richard “Little Dick” West, worked together on a few occasions (see Guns of the Old West fall 2017) and as a result the Doolin and Dalton gangs were constantly being sought by deputies.
By the year 1892 there was no place in the Indian territories that the Dalton gang could consider safe; they all had a price on their heads, and this began to worry Bob Dalton more than anyone else. Years later Emmett Dalton stated that because of the “relentless pursuit” of Heck Thomas, Bill Tilghman and Chris Madsen “the gang wanted to make a big score and then leave the territory for a while.” For the Daltons, the “big heist” in Coffeyville, Kansas, became for them the raid in Minnesota, Northfield, the failed September 1876 bank robbery that had decimated the James-Younger gang 16 years earlier.
