Bad Men of the Indian Nations

By Emerson Hough in 1905

The history of outlawry in Texas finds a parallel in the lands directly to its north, a region long referred to as the Indian Nations. Today, this territory is undergoing a rapid transformation, being divided and allotted as the relentless march of civilization presses onward. This article delves into the history of the Bad Men of the Indian Nations.

The borderlands, that liminal space between the untamed and the settled, have consistently proven to be fertile ground for the growth of outlawry. Within the Indian Territory, a veritable hotbed was created, allowing desperadoes to flourish for generations. The Indigenous peoples themselves, relocated to this supposedly permanent sanctuary by the government, maintained many of their traditional, sometimes savage, customs. In the wake of the tribes’ relocation, a wave of unscrupulous white individuals followed, clinging to the fringes of settlements and resisting the constraints of civilized life.

Intermarriage between white men and Indigenous women became a common occurrence, resulting in a mixed-blood population. A prevailing, though not always accurate, sentiment painted these individuals as inheriting the worst traits of both races while lacking the virtues of either. Adding to this complex mix was a significant infusion of African-American heritage, stemming from the slaves brought in by the Cherokee and further augmented by Black individuals who migrated to the area and intermarried with the tribes.

This mixed-blood population seemed largely averse to the concepts of law and order. Furthermore, the legal system in place differed drastically from that of the established states. The freedom from restraint and the absence of legal repercussions that defined the frontier found their final stronghold here. The Indigenous people, while selectively adopting the less desirable aspects of white man’s law, largely adhered to their own code of blood. The stories of Bad Men of the Indian Nations are filled with blood.

The true number of murders committed within these picturesque savannahs, rugged hills, and expansive grassy plains will forever remain unknown. From the time William Clark, the "Red Head Chief," initiated the government’s efforts to settle the tribes in these lands – then believed to be far beyond the reach of white American settlement – countless lives were lost.

Life in the Indian Nations demanded little in the way of strenuous effort. The readily available resources of the land, the ease of hunting, and the government’s handouts fostered a mindset averse to the steady industry and law-abiding behavior associated with civilization. If a man coveted his neighbor’s possessions, the swift and decisive use of firearms determined the rightful owner. For over half a century, human life was devalued, a condition that persisted well into the era of white settlement. The author recalls hunting expeditions from twenty years prior when venturing into the Nations was considered perilous, regardless of whether one crossed the Neutral Strip or traveled further east among the Osage or Creek Indians. The area south of Coffeyville, Kansas, was then a wild and untamed expanse. However, it is now being settled, crisscrossed by railroads, and gradually transitioning into the hands of white individuals as the Black population relinquishes their lands and the government grants individual titles to the Indigenous people. Back then, the disappearance of a traveler within the timber-covered mountains or blackjack thickets along the rivers was often met with little concern, and many murders went unreported.

The Indian Nations also served as a refuge for individuals fleeing the upper frontier, Texas, or Arkansas. The region had long been a natural sanctuary for the lawless, as well as a designated home for a wild population. Even after the untamed ethics of the cattlemen gave way to the hardly more lawful practices of land speculation, the prevailing creed remained largely unchanged. Tales of the Bad Men of the Indian Nations are filled with stories of outlaws and refugees.

In those earlier days, each man held his own distinct code of conduct and his own unique perspective on the sanctity of property. Consequently, train robberies and bank heists became established industries upon the arrival of railroads and towns in this fertile region, which had long been reserved for hunting. The emergence of gangs led by figures such as the Cook boys, the Wickliffe boys, and the Dalton boys was a natural and logical consequence of the environment. This likelihood was further heightened by the fact that, for a decade or more preceding the large-scale land grabs, the exploits of the James and Younger gangs in train and bank robberies had instilled a widespread belief that the law could be defied with impunity for an extended period.

The Cook Boys operated under this premise until marshals eventually apprehended them, killing one and sending the surviving members to prison.

Given the impossibility of providing a comprehensive account of the countless desperadoes that the Nations have produced over time, it may suffice to highlight a few key aspects of the careers of a particular group that can be considered representative of the Indian Nations brand of outlawry: the infamous Dalton boys.

The Dalton family resided in southern Kansas, near Coffeyville, which was situated close to the border of the Nations. They were engaged in farming, and within the past three or four years, two of the family members were respectable farmers in the vicinity of Coffeyville. The family matriarch still resides near Oklahoma City, where she secured a valuable claim during the opening of the Oklahoma lands to white settlement. The father, Lewis Dalton, was a Kentucky native who served in the Mexican-American War. He later relocated to Jackson County, Missouri, near the home of the notorious James and Younger boys, and in 1851, he married Adelaide Younger. Several years later, they moved from Missouri to Kansas. The couple had thirteen children: nine sons and four daughters.

Charles, Henry, Littleton, and Coleman Dalton were respected and law-abiding citizens. All the sons possessed courage, and many of them attained positions as U.S. Deputy Marshals. Franklin Dalton was killed in the line of duty while serving as a U.S. Deputy Marshal near Fort Smith, Arkansas, in 1887. At the time of his confrontation with a group of horse thieves who resisted arrest, his brother Bob was a member of the same posse. Following Franklin’s death, Grattan Dalton was appointed as a U.S. Deputy Marshal, reflecting the peculiar but effective Western practice of employing dangerous individuals to apprehend other dangerous individuals.

In 1888, Grattan and his posse pursued a troublesome Indian, who, during the altercation, shot Grattan in the arm before escaping. Grattan later served as a U.S. Deputy Marshal in the Muskogee district, where the courts undoubtedly required executives of unwavering courage to deal with the most ruthless and fearless class of criminals the world had ever known. Robert R. Dalton, better known as Bob Dalton, served on his brothers’ posses and soon gained firsthand experience of standing his ground and exchanging gunfire.

He proved to be the most audacious of the family and was later recognized as the clan’s leader in their illicit activities. He also held the position of U.S. Deputy Marshal at the perilous outposts of Fort Smith and Wichita, where he frequently encountered desperadoes from the Nations. For a period, he served as chief of the Osage police and witnessed numerous violent incidents. Emmett Dalton also demonstrated remarkable composure and quickly earned a reputation as a formidable individual to confront.

All the brothers were skilled marksmen, but they seemed to favor the Winchester rifle over the six-shooter in their exploits, which was perhaps a wise decision, as the rifle is undoubtedly more accurate when feasible. In that region, it was customary for men to ride with a rifle positioned under their leg. Uncle Sam had to rely on individuals who proved effective in serving processes for his frontier peace officers. While a coward might possess high moral character, he would not be suitable as a border deputy. The personal character of some of the most renowned Western deputies would hardly withstand close scrutiny. However, the Washington, D.C. government often had to turn a blind eye to such matters. A point was reached when it became increasingly difficult to condone the Daltons’ methods as deputies. In one instance, they absconded with a large number of horses and sold them in a Kansas town. As a result of this incident, Grattan, William, and Emmett Dalton hastily departed for California. There, they became restless and reverted to their old ways, believing that no one on the Pacific Slope had cause to fear them. They held up a train in Tulare County, killing a fireman but being repulsed. William was later acquitted during their arrest and trial, but Grattan was sentenced to twenty years in prison. He escaped from jail before reaching the penitentiary and rejoined Emmett at their familiar haunts in the Nations, Emmett having evaded arrest in California. At the time of their deaths, the Southern Pacific railway had a standing reward of $6,000 for the robbers.

The Daltons were now largely forced into hiding and compelled to make a living through robbery. On May 9, 1891, the Santa Fe train was robbed at Wharton, Oklahoma Territory, and the express car was looted, with the Daltons suspected as the perpetrators. In June of the following year, another Santa Fe train was robbed at Red Rock in the Cherokee Strip. The Frisco train was robbed at Vinita, Indian Territory. A resurgence of the old methods employed by the James and Younger gangs seemed to erupt in the burgeoning railway region of the Southwest. The following month, the Missouri, Kansas & Texas Railway was held up at Adair, Indian Territory, resulting in a fierce shootout between the robbers and the train’s armed guard, who were assisted by townspeople. A local physician was killed, and several officers and citizens were wounded, but none of the bandits sustained injuries, and they escaped with a substantial haul from the express and baggage cars.

At Wharton, they had been less fortunate, as they were apprehended after killing the station agent. One of their men, Dan Bryant, was captured, later killing and being killed by U.S. Deputy Marshal Ed Short.

Dick Broadwell joined the Dalton gang around this time, and they invariably included a few members outside their own family. Their gang was formed and operated along similar lines to the James boys gang of Missouri, whose exploits they emulated and used as a blueprint for their more audacious deeds. In fact, Bob Dalton, the leader, boasted during the Coffeyville raid that he would surpass anything the James boys had ever accomplished by robbing two banks in one town simultaneously.

Bank robbery was a supplementary activity for the Daltons, but they proved reasonably successful at it. They robbed the bank at El Reno, Oklahoma, at a time when only the president’s wife was present, making off with $10,000 and forcing the bank to suspend operations. By this point, the entire country had become incensed against them, as it had been against the James-Younger boys. Pinkerton detectives were offered blanket commissions, and railway and express companies offered rewards amounting to thousands of dollars. For months, each train traversing the Indian Nations was accompanied by a heavily armed guard concealed in the baggage and express cars. Passengers dreaded the journey through that region, and even the slightest pause of the train would elicit fearful whispers of "the Daltons!" It seems almost unbelievable that, in this modern era of rapid railway service, telegraph communication, and increasingly dense settlements, the activities of these men could have persisted for so long. Yet, such was the case. The law proved ineffective and demonstrated its inability to safeguard life and property, as it often has in this country. And, as has often been the case, an outraged society ultimately took matters into its own hands and resolved the issue.

The complete account of the Dalton robberies and murders will remain forever obscured, as the region in which they operated was reticent, guarding its own secrets. However, the climax eventually arrived, thrusting the band into the spotlight of civilized publicity. They straddled the line between savagery and civilization. Now, the press, the telegraph, and the entire infrastructure of modern life were readily accessible. Consequently, their final bold raid, in which they ventured from the land of reticence into the realm of garrulous news gathering, made them more infamous than ever before.

The raid on Coffeyville on October 5, 1892, both established and concluded their reputation as border desperadoes. Rumors had circulated that the Daltons were lurking in the Nations, awaiting an opportunity to raid the town of Coffeyville, but the anticipated attack did not materialize when expected. Therefore, when it finally occurred, it caught the town completely off guard. Bob Dalton spearheaded this endeavor. Emmett was reluctant to participate, arguing that they were too well-known in Coffeyville and that the task would be too demanding for them. However, he agreed to join the party upon realizing Bob’s unwavering determination to proceed regardless. The band at that time consisted of Bob, Emmett, and Grattan Dalton, Bill Power, and Dick Broadwell. Two days before the raid, they rendezvoused near Tulsa, in the Osage country, and spent the night before in the timber along Onion Creek, not far south of town.

They rode into Coffeyville at half-past nine the following morning. The street was somewhat obstructed, so they detoured into an alley approximately one hundred yards from the main street and, dismounting, tethered their horses, leaving them some distance from their intended targets: the First National Bank and the Bank of C. M. Condon & Co.

Grattan Dalton, Dick Broadwell, and Bill Power proceeded to the Condon bank, which was occupied at the time by C.T. Carpenter, C.M. Ball (the cashier), and T.C. Babb (a bookkeeper). Grattan Dalton pointed his rifle at Carpenter, issuing the customary command to raise his hands, while Powers and Broadwell attended to the others. Producing a two-bushel sack, the leader ordered Carpenter to fill it with all the cash, and the latter complied, placing three thousand dollars in silver and one thousand in currency into the sack. Grattan demanded the gold and insisted that an inner safe within the vault be opened. The cashier, Ball, falsely claimed that they could not open the safe, as it was equipped with a time lock that prevented access before half-past nine o’clock. He informed the outlaw that it was twenty minutes past nine (although it was actually twenty minutes to ten), and the latter stated that they could wait ten minutes. However, he grew uneasy and contemplated killing Ball on the spot, suspecting treachery and recognizing the danger of any delay.

It was audacious to sit in the heart of a civilized city, in broad daylight and on the most public street, awaiting the opening of a burglar-proof safe by a time lock. Daring as it was, it was also foolish and futile. As the robbers stood guard over their prisoners, the alarm was raised. Moments later, gunfire erupted, and the bank’s windows were shattered by bullets. The robbers were trapped, Broadwell having been shot through the arm, likely by P.L. Williams from across the street. Yet, they calmly continued their work as best they could, with Grattan Dalton ordering Ball to cut the bag string and empty the heavy silver, which would have hindered their escape. He inquired about a back exit. He was shown a rear door, and the robbers emerged to find themselves in the midst of the most intense street fight they had ever encountered. City marshal Charles T. Connolly had sounded the alarm, and citizens were rushing to the street with weapons they had acquired from hardware stores and their homes.

Meanwhile, Bob and Emmett Dalton had held up the First National Bank, ordering cashier Ayres to hand over the money and terrorizing two or three bank customers who happened to be present. Bob knew Thomas G. Ayres and addressed him by his first name, "Tom," saying, "Go into the safe and get out that money; get the gold, too." He followed Ayres into the vault and discovered two packages of $5,000 each in currency, which he tossed into his meal sack.

The robbers here also poured out the silver and, having cleaned out the bank as they believed, drove the occupants out the front door. As they reached the street, they were fired upon by George Cubine and C. S. Cox, but neither shot found its mark. Emmett Dalton stood with his rifle under his arm, calmly tying the neck of the sack containing the money.

They then both reentered the bank and exited through the back door, which was opened for them by W. H. Shepherd, the bank teller, who, along with Tom Ayres and B. S. Ayres (the bookkeeper), comprised the bank’s personnel. J. H. Brewster, C. H. Hollingsworth, and A. W. Knotts were in the bank on business and were joined by E. S. Booth; all these individuals were left unharmed.

The firing became widespread as the robbers emerged from the two bank buildings. The first man to be shot by the robbers was Charles T. Gump, who stood near the First National Bank armed with a shotgun.

Before he could fire, Bob Dalton shot him through the hand, the same bullet disabling his shotgun. Moments later, a young man named Lucius Baldwin started down the alley, armed with a revolver. He encountered Bob and Emmett, who ordered him to halt, but he continued toward them for an unknown reason. Bob Dalton said, "I’ll have to kill you," and shot him through the chest. He died three hours later.

Bob and Emmett Dalton now exited the alley behind the First National Bank and entered Union Street. There, they saw George B. Cubine standing with his Winchester in his hands, and an instant later, Cubine fell dead with three bullets through his body. Nearby was Charles Brown, an elderly man who was also armed. He was the next victim, his body falling near that of Cubine, although he survived for a few hours after being shot. All four of these victims of the Daltons were shot at distances of approximately 40 or 50 yards and with rifles, as revolvers were generally unreliable at such ranges, even in the hands of experienced shooters. All the gang members carried revolvers, but none used them.

Thomas G. Ayres, formerly a prisoner in the First National Bank, ran into a nearby store as soon as he was released, grabbed a Winchester, and positioned himself near the street door, waiting for the bandits to exit the bank’s entrance. Bob Dalton, who had passed through the alley, spotted him there. Bob took aim and, from 75 yards, shot Ayres through the head. Friends attempted to pull his body back into the store, but they encountered the fire of Grattan Dalton and Powers, who, along with the crippled Broadwell, were now emerging from their alleyway.

T.A. Reynolds, a clerk in the same store, who went to the door armed, was shot through the foot, becoming the third wounded man in that building.

H.H. Isham, one of the store’s owners, aided by M. A. Anderson and Charles K. Smith, joined in the firing. Grattan Dalton and Bill Power were mortally wounded before they had taken more than a few steps from the Condon Bank’s door. Powers attempted to enter a door when he was shot and maintained his footing when he found the door locked, managing to reach his horse in the alley before a second shot killed him. Grattan Dalton also remained on his feet and found cover behind a barn approximately seventy yards from Walnut Street, the main thoroughfare. He stood at bay there and continued firing. City marshal Connolly, carrying a rifle, ran across to a spot near the corner of this barn. He had his eye on the bandits’ horses, which were still hitched in the alley. His back was turned toward Grattan Dalton. The latter must have been injured in his right arm or shoulder, as he did not raise his rifle to his face but fired from his hip, shooting Connolly down from a distance of about twenty feet.

There was a brief lull in the street fight at this point, during which Dick Broadwell, who had been wounded again in the back, crawled into hiding in a lumber yard near the alley where the horses were tied. He crept out to his horse and mounted, but as he started to ride away, he encountered the liveryman, John J. Kloehr, who displayed some of the most impressive shooting by the citizens. Kloehr was hurrying there with Carey Seaman, the latter armed with a shotgun. Kloehr fired his rifle and Seaman his shotgun, and both struck Broadwell, who rode away but fell dead from his horse a short distance outside the town.

Bob and Emmett Dalton, after killing Cubine and Brown and shooting Ayres, hurried to join their companions and reach their horses. They saw F. D. Benson climbing out of a window at an alleyway junction and fired at him but missed. An instant later, as Bob stepped into full view of those who were firing from the Isham store, he was struck by a bullet and badly wounded. He walked slowly across the alley and sat down on a pile of stones, but like his brother Grattan, he kept his rifle firing, despite being mortally wounded. He fired once at Kloehr but was unsteady and missed him. Rising to his feet, he walked a few paces and leaned against the corner of a barn, firing two more shots. He was then killed by Kloehr, who shot him through the chest.

Grattan Dalton was feebly attempting to reach his horse by this time. He passed the body of Connolly, whom he had killed, faced toward his pursuers, and tried to fire. He, too, fell before Kloehr’s Winchester, shot through the throat, dropping close to the body of Connolly.

Emmett Dalton was now the only surviving member of the band. He was still unwounded, and he reached his horse. As he attempted to mount, several shots were fired at him, killing the two horses belonging to Bob Dalton and Bill Power, who by this time had no further use for horses.

Two horses hitched to an oil wagon in the street were also killed by stray shots. Emmett managed to get into his saddle but was shot through the right arm and through the left hip and groin. He clung to the sack of money they had taken at the First National Bank, and he maintained his composure and wits even under such intense pressure. He might have escaped, but instead, he rode back to where Bob was lying and reached down his hand to help him up behind himself on the horse.

Bob was dying and told him it was pointless to try to help him. As Emmett stooped to reach Bob’s arm, Carey Seaman fired both barrels of his shotgun into his back, Emmett dropping near Bob and falling upon the sack containing over $20,000 in cash. Men rushed up and ordered him to raise his hands. He raised his one uninjured arm and begged for mercy. It was assumed he would die, and he was not lynched but was quickly taken to a doctor’s office nearby.

In the small alley where the final scene of this bloody fight unfolded, three dead men, one dying man, and one badly wounded man were found. Three dead horses lay near the same spot. In the entire fight, which lasted only a few moments, four citizens and four outlaws were killed, while three citizens and one outlaw were wounded. Less than a dozen citizens accounted for most of the shooting, with approximately 80 bullet marks found on the front of the Condon bank alone.

News of this bloody encounter spread rapidly across the country, and within hours, the town was inundated with sightseers who arrived by trainloads. The dead bandits were photographed, and the story of the fight was recounted repeatedly, though not always with consistent details. Before being sent to the penitentiary, Emmett Dalton confessed to various previously unknown crimes that the gang had committed.

Thus ended in bloodshed the career of one of the bloodiest bands in the history of robbery, in any land or time. Indeed, it is doubtful that any country has ever witnessed leagues of robbers as desperate as those that existed in America, with hands so stained in blood.

This fact is largely attributable to the country’s unique history, characterized by rapid development fueled by swift modern transportation methods. In America, the westward advance of the fighting edge of civilization, where it clashed and mingled with savagery, occurred more rapidly than in the settlement of any other country in the world. Moreover, this transpired precisely when weapons of the most deadly nature were invented and made readily available, enabling all to own them and many to become exceptionally skilled in their use. The temptation and the means of murder went hand in hand. And in time, the people, not the formal law courts, administered the remedy when the time came for it.

Today, the Indian Nations exist only as a name. Civilization has overtaken them. Statehood has followed territorial organization. Soon, rich farms will create a continuous expanse of grain across what was once a flood of crime, and wheat will grow yellow and cotton white, where the grass was once stained red. The era of the Bad Men of the Indian Nations has passed.

Go To the Next Chapter – Desperados Of The Cities

Compiled and edited by Kathy Alexander/Legends of America, updated April 2024.

About the Author: Excerpted from the book The Story of the Outlaw; A Study of the Western Desperado, by Emerson Hough; Outing Publishing Company, New York, 1907. This story is not verbatim, as it has been edited for clerical errors and updated for the modern reader. Emerson Hough (1857–1923) was an author and journalist who wrote factional accounts and historical novels of life in the American West. His works helped establish the Western as a popular genre in literature and motion pictures. For years, Hough wrote the feature "Out-of-Doors" for the Saturday Evening Post and contributed to other major magazines.