It was not long before things went wrong for the Dalton brothers as lawmen.
In August 1888, Bob, still only nineteen years old, set out to track down Charley Montgomery. As Emmett put it, “Montgomery was a ne’er-do-well, who came from no one knows where and lived no one knew how.”
The word was that Charley was masquerading as a deputy marshal, and this was after having fed false information to Grat about a few recent crimes and then stealing two pistols in Coffeyville. Bob, considered the smartest of the brothers, had discovered Montgomery’s location in Timber Hills. Believing that Grat was busy gambling in Coffeyville, Bob decided to skip alerting his older brother, and instead, he put together his own posse. He did not want to risk that Montgomery would escape the territory.
While approaching the cabin where Montgomery was hiding, the posse began taking fire from the far side of it. In an attempt to flank Montgomery, Bob ran to the southwest corner of the house with a shotgun. When he rounded the corner into the front yard, he ran straight into the fugitive, who was running toward Bob with his pistol raised. Montgomery fired at Bob but missed, even though he had been close enough to leave powder burns on the lawman’s face. A moment later, Bob fired his shotgun and killed Montgomery.
One would think this was a justified killing, but the legal ground was muddy. Unlike Grat, Bob was not a sworn deputy, and he had not waited to obtain a warrant for Montgomery’s arrest. Thus, the fact that Grat was not present meant that Bob could be charged with murder like any other citizen. This sure seemed unfair—and, tauntingly, Bob would show the sign of the powder burns for the rest of his life.*
Making the lives of U.S. deputy marshals—and those who worked for them—even more miserable, as an incentive to take prisoners alive, a marshal would have to bury a suspect himself or pay to have it done when one was killed if no kin could be found. Thus, Bob was forced to pay eighty dollars for Montgomery’s burial and then show up for a preliminary hearing two weeks later, charged with killing him. The hearing lasted until late November, but finally, the testimonies from Bob and posse members about self-defense trumped the technicalities, and they were officially cleared.
However, the event had earned Bob a reputation as a reckless killer, and that stuck to him like a damp shirt wherever he went. It was this stigma dogging him plus guilt over the killing itself that was blamed for Bob becoming a drinker, though he would never match Grat shot glass for shot glass. The alcohol Bob began to regularly sample in Indian Territory was not only bad for his liver but further eroded his reputation and put him on thin ice with the marshal’s office in Fort Smith.
So it was a pleasant surprise in January 1889 when Bob was sworn in as a deputy marshal. This promotion could signal a fresh start for the Dalton brothers. Still, given the paltry pay, it was understandable that Bob took on a second job as a member of the Osage Nation police force. Unlike the U.S. Marshals’ office, the Osage Police paid a monthly salary. Bob hired Emmett under him to guard prisoners. Emmett was two years younger than Bob and looked up to him. Since they were closer in age in comparison to their other siblings, Bob and Emmett had been almost inseparable in childhood and remained close as teenagers.
What appeared to be a promising situation did not stay that way long. It was true of every deputy marshal on the frontier that not only was the pay inadequate, it could also be months before it was issued by the federal bureaucracy in Washington, D.C. The impact on the Daltons was that for awkward stretches of time, the only income the brothers had was what Bob could share on his Osage Police paydays. Inevitably, debts piled up, as did the feelings of frustration.
There was another unfortunate incident that further blemished Bob’s nascent lawing career. In April 1890, a deputy marshal had been shot and wounded near Claremore, Oklahoma, and the suspect was a part-Cherokee man named Alex Cochran. A telegram that found Bob in Tulsa ordered him to track the man down. Bob and Emmett got on a train, and when they arrived in Claremore, Grat, who had received a similar message, was waiting for them.
The brothers did not have to go far. As they walked through town, a local merchant named Davis Hill met them to say that Cochran had just been at his shop to buy a box of cartridges. Even more promising, Hill pointed to a rider down the street and assured the Daltons that he was the suspect. Bob was the first one on a horse and took off in pursuit.
Once Bob was close enough, he halted and dismounted and shouted for Cochran to stop. “Instead of stopping,” Emmett observed, “the man put spurs to his horse and started to run.” Aiming his Winchester and justly confident in his marksmanship, “Bob shot twice, and the horse wheeled to the right and ran all the faster. Then Bob shot twice more. And the horse fell. By this time Grat and I had arrived, and we walked up to where the horse and rider lay.”
An understandable yet still terrible mistake had been made. The rider was the teenage son of Alex Cochran, who had been on an errand for his father. If Bob had not been as good a shot, the boy would still be alive. The deputy marshal had done nothing criminal and he had been given erroneous information, yet his shaky reputation as a lawman took another hit.
No matter: Bob would not be a deputy marshal much longer. His financial frustration did not change under a new marshal, R. L. Walker. He “always had some excuse,” Emmett recalled about Walker. “The government had not made the appropriation. The money would be coming along soon. But ‘soon’ never materialized.”*
In September, Bob went to Marshal Walker’s office to complain about the shortage of pay. The response was being fired. For as long as he could, Bob kept this information to himself and continued with the Osage Police and, with Emmett, kept out of sight by patrolling the outer reaches of the Osage Nation. This also provided a fresh and more reliable source of revenue.
For the next several months, the two brothers would stop any suspicious wagon they could find and would frequently discover stashes of illegal liquor. Rather than making any arrests, Bob chose to fine the culprits himself as well as confiscate their liquor. This was, of course, illegal, but the victims could certainly not turn to the law with their grievances. As for Bob, Emmett rationalized, “Is it any wonder that the thoughts of a young fellow who had gained a fairly good start in life should turn to retaliation and revenge?”
When once more a new marshal took office, Grat was retained as a deputy marshal, but the best Jacob Yoes could do for Bob and Emmett was to offer them positions as possemen for Deputy Floyd Wilson. They accepted, but while waiting to be called upon, Bob and Emmett returned to the outer Osage Nation. Their downfall came on Christmas Day.
Witnesses observed Bob being accompanied by two bootleggers to a holiday celebration held by a group of Osage. During the gathering, jugs of whiskey were openly sold. Worse for Bob, he partook liberally and became quite drunk. An Osage chief named Chi-sho-wah-hah, who owned the home, reported Bob to the marshal. Warrants were issued to Deputy Lafe Shadley for the arrest of both Bob and Emmett on January 7, 1890. Shadley was a friend of the Daltons, and instead of enforcing the warrant, he warned the boys to go into hiding deep in the Indian Territory.
This they did, relying on friends and family for food and shelter. But this was lonely living, and after enough of it, Grat and Deputy Wilson easily convinced Bob and Emmett to turn themselves in. On March 26, they both appeared for their hearing. Emmett was discharged, but Bob was told to appear in the district court at Wichita in a few months. He was released after Deputy Shadley raised the $1,000 bail.
By this time, Grat had his own legal troubles. Earlier that same month, a report was filed about an assault committed by Grat against a man named Delonsdale in Tulsa. The two had gotten into an altercation in the street shortly after Grat had woken up feeling the effects of a long night of drinking and gambling. According to newspaper accounts, he got into an argument and pistol-whipped Delonsdale. Eventually, this would result in him too being fired as a deputy marshal.
For a time, despite the legal clouds hovering over them, Bob and Emmett tried to continue to work as possemen under Grat and Deputy Wilson. Then it was in April that Yoes fired Grat. Bob and Emmett continued working under Deputy Wilson, but they soon gained the impression that they were no longer welcome. On June 20, 1890, Bob told Deputy Wilson that he and Emmett were quitting, and the two left Tulsa.
Worried that he would be found guilty at his upcoming trial, Bob discussed a plan with Emmett to travel to their brother Bill’s ranch in California and that he would write to Bill and Lit Dalton to see if they could find them some work. Bob, still bitter at the Osage chief Chi-sho-wah-hah for snitching on him for drinking at the Christmas party, suggested getting revenge by stealing the chief’s mules and then using the proceeds to fund their trip. Emmett was reluctant, but then, as usual, he was persuaded to go along with Bob’s plan.
In July, Bob and Emmett stole two of Chi-sho-wah-hah’s mules and twenty other unguarded horses they came upon in the Osage Nation. They then drove the impromptu remuda into Indian Territory and tried to sell them to a man from Fort Smith. When the man started asking too many questions, Bob and Emmett took the mules and horses and headed on toward Kansas, where they found a buyer. The brothers found the venture so profitable that they decided to steal another forty horses while still in Kansas.
There had to have been a better idea: When they arrived in Columbus, the Dalton brothers had to dodge several questions about the many brands on their stock. When their buyer, W. W. Scott, showed up, he offered them way below market price. Not having another buyer and wanting to get rid of the illegal stock fast, Bob and Emmett were forced to accept the price. Expecting cash, they were further disappointed when they were handed a check and told to take it or leave it. It got worse: When an irritated Bob took the check to the bank and endorsed it, he used his real name.
And worse still: Apparently not dismayed enough by the previous transaction, Bob and Emmett rounded up another twenty horses in the Osage Nation with the intention of once more selling them to Scott. On their way to the stockyards, however, Bob and Emmett passed the train depot, where they noticed Scott and the owners of the previously stolen remuda, men named Rogers and Musgrove, in conversation. The two men had just finished proving ownership to Scott of their stolen stock and were preparing to drive their reclaimed animals away. Spotting the Dalton brothers, the three men began to point and shout. Bob and Emmett barely escaped, leaving the newly stolen stock behind.
Word got around fast, and several stockmen pulled together a posse to go after the horse thieves. Bob and Emmett thought it prudent to disappear. The two hid out for several months on the bluffs of the Canadian River some seventy miles northwest of Kingfisher, in a dugout they had made on a ranch owned by a man named Jim Riley. They somehow got a message to Grat, who tried to send them food, horses, and ammunition.
This too did not turn out well. Grat was nabbed for aiding and abetting the suspects and tossed into the same jail in Fort Smith where he used to deposit prisoners. He was released after just two weeks—not because of the kindness of the court but because it was hoped he would lead lawmen to his brothers. However, Bob and Emmett had grown tired of hiding and were able to take a train to California. They aimed to pursue the plan to work at their older brother Bill’s ranch near San Miguel in California and lie low until they were mostly forgotten in Kansas and Oklahoma.
Bob and Emmett did find their way to Bill’s ranch. The lying-low part proved more difficult to achieve.