The 1892 Dalton Raid at Coffeyville

On October 5, 1892, the Dalton Gang attempted a dramatic bank raid in Coffeyville, resulting in a fierce shootout that left four gang members dead within minutes. Led by brothers Gratton, Emmet, and Robert Dalton, with two accomplices, they entered two banks, taking around $20,000. However, citizens quickly armed themselves to fight back. Within a short time, the gang was ambushed, leading to numerous casualties, including innocent bystanders. The confrontation ultimately demonstrated the dangers of such criminal endeavors, as the townsfolk decisively ended the gang’s reign of terror.

In all the annals of crime in our country, few if any events have furnished more dramatic incidents or created more of a sensation than the raid of the Daltons at Coffeyville, on the morning of Wednesday, October 5th, 1892. There have been other bank robberies where larger amounts of money have been at stake, and some in which better known bandits and outlaws have participated, but in the sanguinary nature of the struggle, the number of shots fired, and the victims on both sides, the Coffeyville affair must stand preeminent.

The “Dalton Gang,” whose leaders organized and perpetrated this raid had already acquired an unenviable reputation as outlaws and train robbers, and were ready for any crime if the stakes were large enough. Three of the Dalton brothers, with two ordinary criminals of the sort that could be picked up almost anywhere in the Indian Territory, constituted the party. The Dalton family originally consisted of Lewis Dalton and his wife, whose maiden name was Adaline Lee Younger, and who was born in Cass county, Missouri, in the neighborhood whence came other Youngers, who achieved notoriety as bank robbers. They were the parents of thirteen children, of whom two died in infancy. The family were not strangers at Coffeyville, having settled in that vicinity in 1882 and remained there until the opening of Oklahoma in 1889. In fact, Lewis Dalton remained in this county until his death, at Dearing, in 1890. The rest of the family went to Oklahoma and took up claims. The old people seem to have been peaceable and law-abiding, but three of the boys became deputy United States marshals in the Indian Territory, one of them also serving for a short time as chief of police of the Osage Nation. Familiarity with crime and acquaintance with outlaws in these positions seems to have developed a passion for criminal adventure, which may have been also, to some extent, a matter of heredity on their mother’s side. Gratton, Emmet and Robert were the Daltons in the gang, and the two other members of the quintette who raided the Coffeyville banks were known as Bill Powers and Dick Broadwell. Robert, the leader of the gang, was only 22 years of age, while Emmet was a mere boy two years younger. Gratton was 31.

The Daltons are credited with having stolen a herd of cattle in the territory about two years previous to the events to be here narrated, and so far as known, they took the first degree in outlawry at that time. In the early part of 1891, Gratton, William and Emmet Dalton were arrested for train robbery in Tulare county, California. Emmet escaped, William was acquitted, and Gratton was convicted and sentenced to twenty years in the penitentiary. He escaped from the county jail before being taken to Folsom, and there was a standing reward of $6,000 offered for Gratton and Emmet by the Southern Pacific Railway at the time these men met their fate at Coffeyville. In May 1891 there was a train robbery by masked men at Wharton, Indian Territory, on the Santa Fe Railroad; and in July of the same year another at Adair, on the Missouri, Kansas & Texas, both of which were credited to the Daltons.

On the morning of the Coffeyville raid, the five men mentioned were seen by several people riding toward that city, and they were taken, in every instance, for a United States Deputy Marshal and his posse. They came in on the main road from the west, turned south one block from the business part of town and hitched their horses in the alley running back from Slossen’s drug store, which has since become famous as “the Alley of Death.” They then started down the alley, Gratton, with Powers and Broadwell in front, and Emmet and Bob following. As they crossed the sidewalk, on emerging from the alley, they passed within five feet of a citizen who was acquainted with them well enough to recognize them in spite of the disguises they had assumed on coming into a locality where they were so well known. A moment later he saw the three men who were in front enter C. M. Condon & Co.’s bank and present a Winchester at the cashier’s counter. He raised the alarm at once.

Meantime the other two had crossed Union street and entered the First National bank. They were followed by some citizens who suspected their object and the alarm was speedily raised on the east side of the plaza, also. Immediately half a dozen men rushed to the hardware stores of Isham Bros. & Mansur and A. P. Boswell & Co., on the east side of Union street, and proceeded to provide themselves with rifles and ammunition, determined that the bank robbers should not get away if it was possible to prevent it.

In Condon & Co.’s bank were C. T. Carpenter, one of the proprietors, Chas. M. Ball, the cashier, and T. C. Babb, the bookkeeper. The leader of the raiders, Grat. Dalton, ordered the men behind the counter to throw up their hands; and on looking up from his work at the desk, Mr. Carpenter saw three Winchesters aimed at his head, and heard such reassuring words as these:

“We have got you. G—d you! Hold up your hands.”

As soon as Dalton had passed around into the inside of the enclosure at the bank, he ordered Mr. Ball to hold a grain sack he had brought with him, while Carpenter was told to put the money in the canvas sacks in the safe into it. There was $3,000 in silver in the three sacks, and when he had got that Dalton ordered Mr. Ball to open the burglar proof chest in the vault. Ball replied:

“It is not time for it to open.”

“What time does it open?” asked Gratton.

“Half past nine,” answered Ball, guessing what o’clock it might be, sparring for time.

“What time is it now?” queried the bandit.

“Twenty minutes past nine,” glibly answered Ball, looking at his watch.

As a matter of fact, it was twenty minutes of ten, but Dalton did not know this and calmly proposed to wait until the chest could be opened. In a moment or two he began to suspect the truth and turned on Ball and cursed him and threatened to put a bullet through him. With the money from the counter the robbers now had $4,000, but the firing which had begun from the outside was getting so hot that the robbers ordered the sack carried into the back room, where the currency was sorted out and the silver left. The bankers and two customers who happened to be in when the raid was made, were lying on the floor now to escape the rain of bullets that came crashing through the plate glass. Broadwell had already received a bullet in the arm that disabled him, and the robbers made haste to get out into the street whence they had come.

Meanwhile, a good deal had been happening at the First National across the street. Bob Dalton and Emmet entered here about the same time the other three men went into Condon’s. They covered the cashier, Thomas G. Ayres, and the teller, W. H. Shepard, with their guns and ordered everyone present to hold up his hands. The men in the bank in front of the counter at the time were J. H. Brewster, the well-known contractor, who built the county court house, A. W. Knotts, who was afterward deputy sheriff, and C. L. Hollingsworth. Leaving Emmet on guard in front, Bob went around to the rear and entered the private room, where he found Bert S. Ayres, the bookkeeper, and ordered him to go to the front and get the money on the counter. He then ordered the cashier to bring him the money that was in the safe, and not satisfied with what he got went into the vault himself and took two packages of currency containing five thousand dollars each, and added them to the collection in his sack, which now amounted to $20,000. Ordering the bank force and customers out before them, the bandits started to go out the front door, but some shots drove them back and they then retreated by a back door.

Right at this time the murderous work began. So far, only two men had been wounded, Broadwell, on the inside of Condon’s bank, and Charles T. Gump, who had taken a position outside of the First National with a gun ready to shoot at the robbers when they started out. Bob Dalton fired a shot which struck him in the hand and disabled him. When the two robbers emerged from the rear door of the First National, having the teller, Mr. Shepard with them, they came across Lucius M. Baldwin, a clerk from Reed Brothers’ store. He was holding a revolver at his side and coming forward as if to join the others. Both the Daltons leveled their Winchesters at him and commanded him to stop. For some reason he failed to obey and kept moving toward them. Bob remarked, “I’ll have to get that man,” and pulled the trigger which sent a bullet through Baldwin’s breast near the heart. He was only about fifty feet away at the time. He was picked up by friends and carried away but only survived for about three hours.

The Daltons ran north up the alley to Eighth street and turned west when they reached that street. When they got as far as Union street on the east side of the Plaza, they looked down that street to the south and fired a couple of shots, apparently for the purpose of frightening their assailants away. By the time they had reached the middle of the street on their way across to the “Little block” in the center of the Plaza, they discerned George Cubine standing in the doorway of Rammel Brothers’ drug store, which adjoined the First National bank building on the north. He had a Winchester in his hand and was looking the other way, toward the door of the bank from which he was expecting to see the outlaws emerge. They each fired twice at him, and as the four shots rang out, he fell to the pavement lifeless, with one bullet through his heart, another through his left thigh and a third through his ankle. The fourth ball went astray and crashed through the plate glass window of the store behind him. Charles Brown, an old man whose place of business was next north of the drug store, rushed out to assist the fallen man; but seeing that he was dead, seized the Winchester Cubine had and turned it on his slayers. Four more deadly shots rang out from the bandits’ guns, and Brown fell bleeding and dying. He survived three hours in dreadful agony and then passed away.

These three murders had been committed in less time than it has taken to tell it. By this time the Daltons caught sight of another man who was watching the entrance of the bank, ready to fire when they should emerge. When turned out of the bank at the time the outlaws started to come out the front way, Cashier Ayres ran into Isham’s hardware store, just to the south, and procured a Winchester, with which he took a position in the doorway, where he could command the entrance to the bank. As they were stepping up onto the sidewalk on the west side of Union street, and across the street from the Eldridge House, Bob took deliberate aim at Ayres, who was about seventy-five yards distant, and fired a bullet which struck him in the cheek, just below his left eye and came out at the back of his head near the base of the skull. He fell bleeding and unconscious and for days hung between life and death, but finally recovered.

Just at this time, Gratton and his companions had reached the alley adjoining Slosson’s store, up which they had left their horses, and before the prostrate form of Mr. Ayres could be removed they fired nine shots into the front of the building where he lay. Bob and Emmet proceeded west on Eighth street and were not noticed again until they reappeared near the junction of the two alleys, having come down back of Wells Brothers’ store. Their escape would have been comparatively easy, had they not returned to that spot, but made a break for the open country and taken the first horse they came across.

As it was, the whole force of the bandit band was now gathered in what has since been known as “the Alley of Death,” and there they all fell beneath the bullets of the volunteers for law and order, though not until another good citizen lost his life. For the facts thus far published we are indebted to the painstaking and carefully written work published by Colonel D. Stewart Elliott, of the Coffeyville Journal, entitled: “Last Raid of the Daltons;” and for the story of the concluding scenes of that raid we can do no better than to reproduce the chapter of that work on “The Alley of Death” almost verbatim.

When the alarm was first given that the banks were being robbed, Henry H. Isham, the senior member of the firm of Isham Brothers & Mansur, was busy with a customer, as were two clerks in the store, Lewis T. Dietz and T. Arthur Reynolds. This store not only adjoined the First National bank on the south, but from its front a clear view is to be had across the Plaza and up the alley at the west side to which the Daltons first came and to which they finally retreated. Mr. Isham dismissed his customer, closed his safe, and, grasping a Winchester, stationed himself near a steel range in the front of the store where he could see all that was going on in the front part of Condon’s bank. Dietz snatched a revolver and stationed himself close to Isham, while Reynolds, having observed the robbers enter the banks, was so eager to prevent their escape that he seized a Winchester, ran out upon the sidewalk and commenced firing upon the robber who was stationed near the southeastern door of the Condon bank. A shot from the latter’s rifle struck some intervening object and glanced and hit Reynolds on the right foot at the base of the little toe, coming out at the instep. He was the third man wounded in the store, and was now forced to leave the field. Indeed, with its blood-bespattered floor, the store now began to look like a slaughter house or a section of a battle field. M. N. Anderson, a carpenter, who had been at work a couple of blocks away, now arrived and took the Winchester Reynolds had dropped and stationed himself beside Isham, where he performed valiant service until the close of the engagement. Charles K. Smith, a young man from a barber shop near Isham’s store, also procured a Winchester and joined the forces in the hardware store in time to help exterminate the gang.

From five to nine shots were fired by each man who handled a Winchester at this point. The principal credit, however, for the successful and fatal work done at the store was due to Mr. Isham. Cool and collected, he gave directions to his companions and at the same time kept his own gun at work.

The moment that Grat. Dalton and his companions, Dick Broadwell and Bill Powers, left the Condon bank after looting it, they came under the guns of the men in Isham’s store. Grat. Dalton and Bill Powers each received mortal wounds before they had gone twenty steps. The dust was seen to fly from their clothing, and Powers in his desperation attempted to take refuge in the doorway of an adjoining store, but the door was locked and no one answered his request to be let in. He kept his feet and clung to his Winchester until he reached his horse, when another ball struck him in the back and he fell dead at its feet. Grat. Dalton, getting under cover of an oil tank which had been driven into the alley just about the time the raid was made, managed to reach the side of a barn on the south side of the alley, about two hundred feet from Walnut street. The point where he stopped was out of the range of the guns at Isham’s on account of an intervening outside stairway. He stood here for a few minutes firing wild shots down the alley toward the Plaza.

About this time John J. Kloehr, a liveryman, Carey Seaman, and the City Marshal, Charles T. Connelly, who were at the south end of the Plaza, near Reeds’ store, started up Ninth street so as to intercept the gang before they could reach their horses. Connelly ran across a vacant lot to an opening in the fence at the alley, right at the corner of the barn where Grat. Dalton was still standing. There he sprang into the alley, facing the west where the horses were hitched. This movement brought him with his back toward the murderous Dalton, who was seen to raise his Winchester to his side and, without taking aim, fired a shot into the back of the brave officer. Connelly fell forward on his face, within twenty feet of where his murderer stood. He breathed his last just as the fight ended.

Dick Broadwell, in the meantime, had reached cover in the Long-Bell Lumber Company’s yards, where he lay down for a few moments. He was wounded in the back. A lull occurred in the firing after Grat Dalton and Bill Powers had fallen. Broadwell took advantage of this and crawled out of his hiding place, mounted his horse and rode away. A ball from Kloehr’s rifle, and a load of shot from a gun in the hands of Carey Seaman, overtook him before he had ridden twenty feet. Bleeding and dying he clung to his horse and passed out of the city over a portion of the road by which the party entered it not more than twenty minutes before. His body was subsequently found by the roadside half a mile west of the city, and his horse with its trappings was captured near where he fell.

Almost at the same moment that Marshal Connelly went down before the deadly rifle of Grat. Dalton, Bob and Emmet emerged from the alley by which they had left Eighth street in their effort to rejoin the rest of the party where their horses had been left. They had not met with any resistance in passing from where they had shot Cubine, Brown and Ayres, as the firing toward the south end of the Plaza had attracted general attention in another direction. The north and south alley through which they reached “the Alley of Death,” has its terminus opposite the rear end of Slosson’s store. When they reached the junction of the alleys, they discovered F. D. Benson climbing through a rear window with a gun in his hand. Divining his object, Bob fired at him point blank, at a distance of not over thirty feet. The shot missed. Bob then stepped into the alley and glanced up at the tops of the buildings as if he suspected the fusillade that was pouring into the alley came from that direction. As he did so, the men at Isham’s took deliberate aim from their positions in the store and fired at him. The notorious leader of the Dalton gang evidently received a severe if not fatal wound at this time. He staggered across the alley and sat down on a pile of dressed curbstones near the city jail. Still true to his desperate nature, he kept his rifle in action and fired several shots from where he was sitting. His aim, though, was unsteady and the bullets went wild. While sitting on the rocks he espied John Kloehr on the inside of the fence near Slosson’s store. He tried to raise his Winchester to his shoulder, but could not, and the shot intended for Kloehr struck the side of an outhouse and failed in its mission. Bob Dalton then made his supreme effort. He arose to his feet and sought refuge alongside of an old barn west of the city jail, and, leaning against the southwest corner of the building he brought his rifle into action again and fired two shots in the direction of his pursuers. They were his last shots. A ball from Kloehr’s rifle struck him full in the breast and he fell over backward among the stones which covered the ground there, and which were reddened with his life blood.

After shooting Marshal Connelly, Grat. Dalton made another attempt to reach his horse. He passed by his fallen victim, and had advanced probably twenty feet from where he was standing when he fired the fatal shot; then turning his face to his pursuers he again attempted to use his Winchester. John Kloehr’s rifle blazed out again now, and the oldest member of the band dropped with a bullet in his throat and a broken neck. He fell within a few feet of the dying marshal.

Up to this time Emmet Dalton had managed to escape untouched. He kept under shelter after he reached the alley until he attempted to mount his horse. A half dozen rifles were then fired in his direction, as he undertook to get into the saddle. The two intervening horses belonging to Bob Dalton and Bill Powers were killed by some of the shots intended for Emmet; and the two horses attached to the oil tank-wagon being directly in range received fatal wounds. Emmet succeeded in getting into the saddle, but not until he had received a shot through the right arm and another through the left hip and groin. During all this time he had clung to the sack containing the money he had taken from the First National bank. And then, instead of riding off, as he might have done, Emmet boldly and courageously rode back to what he must have known was almost certain death and came up beside where Bob was lying and attempted to lift his dying brother onto the horse with him. “It’s no use,” faintly whispered the fallen bandit, and just then Carey Seaman fired the contents of both barrels of his shot-gun into Emmet’s back, as he was leaning over the prostrate form of his leader and tutor in crime. The youthful desperado dropped from his horse and the last of the Dalton gang was helpless. In falling, the sack containing the twenty thousand dollars he had perilled his soul and body to get went down with him, and he landed at the feet of his brother, Bob, who breathed his last a moment later.

Citizens who had followed close after the robbers, and some of whom were close at hand when they fell, immediately surrounded their bodies. Emmet responded to the command to hold up his hands by raising his uninjured arm and making a pathetic appeal for mercy. Lynching was suggested, but better counsels prevailed and he was taken to the office of a surgeon, who dressed his wounds. He recovered with the quick elasticity of youth and was taken to the jail at Independence, where, in the following March, he pleaded guilty to murder in the second degree and was sentenced to a ninety-nine years’ term in the penitentiary, ten of which he has already served. His aged mother is untiring in her efforts to secure pardon and freedom for her wayward boy, but no governor has yet dared to brave the indignation of the friends of the victims of the raid by granting her prayer.

Less than fifteen minutes had elapsed from the time the raiders entered the banks until four of them were dead and the others helpless with wounds. And it was only twelve minutes from the firing of the first shot until the last one sounded the knell of the Dalton gang.

Summarizing the reports, it appears that eighty bullet marks and numerous evidences of the impact of small shot were visible on the south front of Condon’s bank when the battle ended. Not more than fifteen guns were actively engaged in the fight on both sides; and yet eight people were killed and three wounded. While all the citizens who were killed or wounded were armed, George Cubine was the only one of them who had fired a shot before being struck down. Among the scores of bystanders and onlookers about the Plaza, including many girls and little children, not one was struck by a shot or bullet. It was war, and very sanguinary war, while it lasted, the percentage of victims to combatants being greater than in any battle that was not a massacre; but no wild shooting was done.

While the people of Coffeyville wiped out the outlaw gang at a terrible cost of valuable lives, they insured their city against any more such visitations during the lifetime of the present generation, and conferred a service upon the state and upon society by demonstrating how risky and unprofitable such raids are likely to prove.