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GOW Spring 2018On the trail of the Dalton GangFamily ties that broke the law 1/2

By Dennis Adler


A hail of lead shot past Emmett Dalton’s head as his horse spun around like a dog chasing its tail; a rifle slug found its mark glancing off his right hip, another cut into his groin, he was hit in the right arm, and moments later a shotgun blast took him clean out of the saddle. He hit the ground just a few feet from where his brother Bob had been shot and lay dying. Up until that moment Emmett had been the only one of the gang who hadn’t been shot and he might have made it out of town if he hadn’t tried to go back and rescue Bob.


Although Bob Dalton (far right) was much younger than Grat (top) he had become the gang’s leader by 1891. Youngest brother, Emmett (left) was the come-along kid, following older brother Bob’s lead. It was Bob’s decision to purchase new guns for the gang before the Coffeyville raid. Standing in for the 5-1/2 inch engraved model Colts Dalton had procured (insert), are a trio of new Traditions 4-3/4 inch blued and engraved “Bill Tilghman” models. There is quite a bit of irony in this since Tilghman, and fellow U.S. Deputy Marshals Heck Thomas and Chris Madsen’s pursuit of the Dalton and Doolin gangs had led Bob into the high stakes dual bank robbery in Coffeyville. (Bob Dalton’s Coffeyville Colt Peacemaker photo courtesy Rock Island Auction Co.)


His older brother Grat had already been shot dead a few yards away along with Dalton gang member Bill Power, in what would come to be known as “Death Alley.” As Emmett watched the life fade from his brother’s eyes, men with rifles and shotguns surround them, and at that moment he expected to die as well. Amazingly, although he had 23 wounds, Emmett Dalton did not die. He would be the only one of the five Dalton gang members to survive the most ill-fated bank robbery in western history. It had taken just 15 minutes in Coffeyville, Kansas, to end the careers of one of the most notorious outlaw gangs of the early 1890’s American West.


Before Coffeyville

Some would say that the Dalton boys were predisposed to a life of crime having grown up in the shadows of Frank and Jesse James, and the Younger Brothers, Bob, Cole and Jim. They were, in fact, closer to the famed outlaw gang than almost anyone else.


They were related, their mother, Adeline Younger, was Cole, Bob, and Jim Younger’s aunt and a cousin to Frank and Jesse. But even though they were kin to the most infamous outlaws of the day, living outside of the law didn’t necessarily hold true for the Dalton family in the 1880s, including Bob, Grat, and Emmett and their older brother Frank, who was a respected U.S. Deputy Marshal.


As young men growing up in Missouri, Oklahoma, and Kansas the boys had hardly been in any serious trouble at all. Originally from Missouri, the Dalton family had moved around over the years spending time in Kansas City, Kansas, then in northeast Oklahoma in 1882.


In 1886 they moved to Coffeyville in southeast Kansas. By then Grat was 25, Bob 17, and Emmett 15 years old. Frank was two year’s Grat’s senior and working out of Judge Isaac Parker’s court in Ft. Smith, Arkansas. Tragically, less than a year after the family moved to Coffeyville, Frank would be murdered, an event that would begin to change everything for the three younger Dalton brothers. Frank had been on the trail of an outlaw gang when he was ambushed and killed in a shootouton November 27, 1887.


Gratton “Grat” Dalton was the oldest of the three Dalton Brothers and had lived a fairly quiet life until his older brother Frank, a U.S. Deputy Marshal, was killed in the line of duty in November 1887. Grat followed in Frank’s footsteps becoming a U.S. Deputy Marshal, initially working out of Judge Isaac Parker’s court in Ft. Smith, Arkansas, just as his brother Frank had. By 1890 he would go from chasing men on wanted posters to becoming one of the men on a wanted poster.

This prompted Grat to take up his late brother’s job as a U.S. Deputy Marshal in Ft. Smith. Bob followed suit within a year, putting on a U.S. Deputy Marshal’s badge in 1888 and working out of the Federal Court in Wichita, Kansas. Part of his duties included chasing down outlaws, gun runners and bootleggers in the Osage Nation Indian Territory.


Emmett was only 21 when his brother Bob led the gang into Coffeyville. He had been a working cowboy, tall, good looking and outwardly flamboyant. His floral carved and studded rig was indicative of a young “show off” outlaw’s gear. The gun belt was lined and had Emmett Dalton’s initials spelled out in nickel studs on the tongue end. There is a black and white photo that can be found on page 151 of Guns and the Gunfighters, by the editors of Guns & Ammo, (1982) documenting that the original of this holster was in the Museum of the Great Plains.

Even their youngest brother, Emmett, a working cowboy at the time, was occasionally deputized to ride in Grat or Bob’s posses, so he too had worn a badge before the Dalton boys turned to a life of crime in 1890. How they went astray from enforcing the law to becoming outlaws begins and ends with Bob Dalton.


Bob had a wild streak and putting on a Deputy U.S. Deputy Marshal’s badge at age 19 had further emboldened him. Shortly after becoming a Marshal he killed his first man. Bob claimed it was in the line of duty, others said differently, but young Dalton remained a Deputy Marshal until March of 1890, when he was arrested for having sold whiskey to members of the Osage Nation the previous December 25th.


It cost him his badge but he was released on bail pending a trial in September. At about the same time, Grat was charged with allegedly stealing horses. The charges were proven to be unfounded and summarily dropped, but soon after he was discharged of his duties; Bob and Grat’s careers as lawmen were over, and their careers as outlaws had just begun. Bob skipped bail and the two brothers left the Indian Territory.They spent a brief time in New Mexico, where they pulled off their first heist in a gambling hall, and then headed to California where another brother, Bill, owned a ranch.


There were many outlaws who had started out as lawmen, (and more than a few outlaws who later became lawmen), but Bob Dalton started early, becoming a U.S. Deputy Marshal at the age of 19. In less than two years he would lose his badge and become leader of one of the most notorious gangs of train robbers in the Indian Territory.

Like his late brother Frank, Bill Dalton had eschewed a life of crime. He was married and involved in California politics, which in 1890 meant very vocal land disputes between ranchers, farmers and the mighty Southern Pacific Railroad. For whatever reason, Bob and Grat decided to “help” the cause and convincing Bill and Emmett to join them, they attempted to hold up a Southern Pacific train headed to Los Angeles on February 6, 1891.


It did not go as planned, they ended up shooting and killing the engineer and finding the Express Car locked with no way to force the Express Agent inside to open it. After a few minutes they ended up riding off empty handed with a murder charge hanging over their heads. Bob and Emmett escaped and headed back to Oklahoma but Grat and Bill were captured and stood trial. Bill was acquitted perhaps because of his political ties, but Grat was sentenced to 20 years.


He never served a day. He managed to pull off a daring escape from a moving train while en route to prison. He headed back to the Oklahoma Indian Territory to meet up with Bob and Emmett.


Return to the Indian Territory

Bob and Emmett had already formed a small gang with a few of Emmett’s old cowboy friends. They pulled off their first successful train robbery in May 1891. In September they robbed another train and got away with around $10,000. The Dalton gang struck the railroads again in June and July of 1892 along with George “Bitter Creek” Newcomb, Bill Power, Dick Broadwell, Charlie Pierce, and Bill Doolin, who would later split off and form his own gang. By then, Bill Doolin, Bob, Grat and Emmett Dalton were among the most wanted train robbers in the territory.


The Dalton and Doolin gangs, the latter comprised of George Newcomb, “Dynamite Dan” Clifton, William F. “Little Bill” Raidler, and Richard “Little Dick” West, occasionally rode together (see Guns of the Old West Fall 2017) and thus the Doolin and Dalton gangs were continually pursued by U.S. Deputy Marshals. By 1892 there was nowhere within the Indian Territories that the Daltons could call a safe haven, they all had prices on their heads, and this began to wear on Bob Dalton more than the others.


Years later Emmett Dalton remarked that because of Heck Thomas, Bill Tilghman and Chris Madsen’s “…unrelenting pursuit, the gang wanted to make one big score then leave the territory for a time.” For the Daltons, the “big score” in Coffeyville, Kansas, turned into their Northfield, Minnesota Raid, the botched September 1876 bank robbery that had decimated the James-Younger gang 16 years earlier.

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