In Southeast Kansas and the four-state area there is so much “wild west” history, I have a hard time keeping these posts short! There are many details that have been left out, and some details here may be arguable. In this area, I know Dalton and James descendants. Several area towns still have ‘Jesse James’ days. Please enjoy this condensed history. ~sekanblogger

Coffeyville's Condon Bank Today

Coffeyville's Condon Bank Today

 Lewis Dalton was a saloon keeper in Kansas City, Kansas, when he married Adeline Younger, the aunt of Cole and Jim Younger, other famous outlaws who rode with Jesse James and gang. In 1882 the family lived in northeast Oklahoma, and by 1886 they had moved to Coffeyville in southeast Kansas. When the Oklahoma Territory opened for settlement in 1889, the family homesteaded Kingfisher Oklahoma. (My own Grandfather was a child in this same Oklahoma land rush.)  The Dalton’s had 15 children, 13 survived to adulthood. One son, Frank, was a U.S. Deputy Marshal who was killed in the line of duty in 1887. Hoping to avenge their brother’s death, the three younger Dalton boys-Grattan “Grat” (b. 1861), Bob (b. 1869), and Emmett (b. 1871)–became lawmen. By 1890, the boys had made the change from lawmen to outlaws.

Bob Dalton was always the wild one. He killed a man for the first time when he was just 19. In March 1890, Bob was charged with introducing liquor into Indian Territory (now Oklahoma), but did not appear for his trial. In September 1890, Grat was arrested for stealing horses–a hanging offense, but either the charges were dropped or he was released. Discredited as lawmen, the Daltons soon formed their first gang. Bob recruited George “Bitter Creek” Newcomb, Bill McElhanie, and “Blackfaced Charley” Bryant to ride with him and his brother Emmett. Grat Dalton joined in later, as did Bill Doolin, Dick Broadwell, and Bill Powers. Their first robbery target was a gambling house in Silver City, New Mexico.

In February 1891, the ‘Dalton Gang’ was in California and Southern Pacific passenger train was held up. The Daltons were accused of the robbery, based on little evidence. Bob escaped and Bill was acquitted, but Grat was arrested, convicted, and put on a train headed for a 20-year prison sentence. Grat was handcuffed to one deputy and accompanied by another. Suddenly, Grat jumped up and dived head first out of the train window. He landed in the San Joaquin River, disappeared under water, and was carried downstream by the current. The deputies were astounded. Grat must have taken the key to the handcuffs from the deputy’s pocket as he slept and then timed his escape to take place when he knew the train would be on a bridge. Somehow he found his brothers and made his way back to Oklahoma Territory. The Dalton brothers were now professional outlaws. Between May 1891 and July 1892 they robbed four trains in Indian Territory.

 In June 1892, they stopped another Santa Fe train, this time at Red Rock. Blackfaced Charley Bryant and Dick Broadwell held the engineer and fireman in the locomotive. Bob and Emmett Dalton and Bill Powers walked through the passenger cars, robbing the passengers as they went. Bill Doolin and Grat Dalton threw the safe out of the train. They only got a few hundred dollars, and it wasn’t long until Blackfaced Charley was caught and killed in an escape attempt.

The gang struck again in July at Adair near the Arkansas border. They first robbed the train station, then calmly sat waiting. When the train came in at 9:45 p.m., they backed a wagon up to the express car and unloaded the loot. There were 11 armed guards on the train, but for some reason all were at the back of the train. The guards fired at the bandits from behind the train. None of the Dalton gang was hit. Three guards were wounded and a town doctor was killed by a stray bullet.

Condon Bank after robbery

Condon Bank after robbery

 The gang could have kept themselves busy with train robberies, but Bob Dalton wanted to make sure his name would long be remembered. He would, he claimed, “beat anything Jesse James ever did–rob two banks at once, in broad daylight.” On October 5, 1892, the Dalton Gang attempted this feat when they set out to rob the C.M. Condon & Company’s Bank and the First National Bank in Coffeyville, Kansas.

By this time,  Cole Younger was serving a 25-year sentence for his part in a bank robbery attempt. From his prison cell he warned his Dalton cousins against a life of violence and crime, but they would not listen. These former Coffeyville residents planned to outdo the James Gang by using the town as the setting for a spectacular double bank robbery. The robbery ended, however, with four of the five outlaws dead. Coffeyville became famous all over the country as the “town that stopped the Daltons.”


Bob & Grat Dalton as Trophies!

Bob & Grat Dalton as Trophies!


DALTONS! The Robber Gang Meet Their Waterloo in Coffeyville. The Outlaws Beaten at Their Own Game.

The fifth of October, 1892, will be marked in the history of the city of Coffeyville, in fact in the current history of the country, as the date on which one of the most remarkable occurrences of the age took place. Between 9:30 and 10:00 on Wednesday morning, [five men], armed to the teeth and apparently disguised, rode boldly [into town]. They entered an alley and hitched their horses to the fence. They quickly formed into a sort of military line, three in front and two in the rear. Aleck McKenna was in front of his place of business when the men came out of the alley, and they passed within five feet of where he was standing. He recognized one of them as a member of the Dalton family. The men quickened their pace and three of them went into C. M. Condon & Co.’s bank while two ran directly across the street to the First National bank. The next thing that greeted Mr. McKenna’s eyes was a Winchester pointed toward the cashier’s counter in the [Condon] bank. He called out that “the bank was being robbed.” The cry was taken up and quickly passed from lip to lip all around the square. The unwelcome visitors in this bank were in plain view of a score or more people on the plaza.

Grat Dalton, disguised by a black moustache and side whiskers, led the raid on Condon and Co.’s bank. He sternly commanded the clerk to hand over the cash on hand, and urged him to be quick about it. The robber gathered up the funds and carelessly stuffed them in the inside of his vest. One of the other men passed into the office. He ordered Mr. C. M. Ball, the cashier, to bring the money out of the safe. Mr. Ball told him that the time lock was on and that he could not get into the money chest. The fellow told him that he would have to get into it, or he would be compelled to kill him. [The robber] inquired how soon the time lock would open. Mr. Ball told him that it was set for 9:45. “That is only three minutes yet, and I will wait,” replied the intruder. Before the three minutes had expired, firing began on the outside of the bank, and the bullets began to come through the plate glass windows. All three men rushed out in the direction of the alley where their horses were hitched.

It may be stated in this connection, that Mr. Ball’s story about the time lock was purely fictitious. It was set for eight o’clock and had opened at that hour. The fact that there was over forty thousand dollars in the chest influenced the cool headed cashier to lie to the burglar.

Bob Dalton, the acknowledged leader of the outfit, disguised by false moustache and goatee, accompanied by his youngest brother, Emmett, entered the First National bank. They covered the teller and the cashier with their Winchesters and, addressing the cashier by name, directed him to hand over all the money in the bank. The cashier very deliberately handed over the currency and gold on the counter, making as many deliveries as possible, in order to secure delay in hope of help arriving. The money [was] stuffed into a common grain sack and carefully tied up. [At the sound of] a shot from outside, [the bandits went] out through the back door of the bank. Just at this juncture, Lucius M. Baldwin came out of Isham’s hardware story. Bob Dalton drew up his Winchester, fired, and Baldwin fell dying in the alley. Bob Dalton raised his gun and fired in the direction of the bank, and George Cubine, a man who had been his acquaintance and friend in former years, fell dead. Reaching the middle of the street, he fired another shot, and Charles Brown fell. Bob Dalton raised his gun and fired the fourth shot. His victim this time was Thomas Ayers, cashier of the First National bank. Emmett Dalton had run ahead of Bob with the grain sack containing over $21,000 over his shoulder. Bob and Emmett joined Grat Dalton and his party in the alley. It was at this point, in this now historic alley, that the daring highwaymen met their doom.

In the meantime, as many citizens as could so do, had procured arms and secured positions where they could command the point of retreat of the highwaymen. H. H. Isham and L. A. Deitz had stationed themselves behind two cook stoves near the door of the hardware store. A dozen men with Winchesters and shot guns made a barricade of some wagons. The robbers had to run the gauntlet of three hundred feet with their backs to a dozen Winchesters in the hands of men who knew how to use them. The firing was rapid and incessant for about three minutes, when the cry went up; “They are all down.” Several men who had been pressing close after the robbers sprang into the alley and covering them with their guns ordered them to hold up their hands. One hand went up in a feeble manner. Three of the robbers were dead and the fourth helpless. Between the bodies of two of the dead highwaymen, lying upon his face, was Marshal T. Connelly, the bravest of all the brave men who had joined in resisting the terrible raiders in their attempt to rob the banks. Dead and dying horses and smoking Winchesters on the ground added to the horrors of the scene. Tearing the disguises from the faces, the ghastly features of Gratton and Bob Dalton, former residents of Coffeyville and well know to many of our citizens, were revealed. The other dead body proved to be that of Tom Evans, whilst the wounded man was Emmett Dalton, the youngest brother of the two principals of the notorious gang.

It was well known that one of the party had escaped, and a posse was hastily organized and started in pursuit. [In] a half mile, they came upon the bandit lying [dead] beside the road. He proved to be John Moore, the “Texas Jack” of the gang. His proper name was Richard Broadwell, and he was one of the most experienced and coolest of the gang. The dead raiders were put in the city jail.

Not over fifteen guns were actively engaged in the fight of Wednesday on both sides and the engagement lasted about ten minutes. Eight persons were killed and three wounded.

The unfounded reports that have been sent out by excited newspaper correspondents to the effect that the citizens were anticipating a visit from the Dalton gang is a canard of the worst kind, and is a reflection upon the courage and promptness to act on the part of our people. When the robbers were discovered, there was not a single, solitary armed man anywhere upon the square or in the neighborhood. Even Marshal Connelly had lain his pistol aside. Every gun that was used, with the exception of that brought into action by George Cubine, was procured in the hardware store and loaded and brought into play under the pressure of the great exigency that was upon the people. The citizens of Coffeyville who were killed in the terrible engagement with the Daltons were each one engaged in the fight, and were not innocent bystanders. Our people are adept in the business of resisting law-breakers, and they will do their duty, though it costs blood.

deaddaltonsThe smoke of Wednesday’s terrific battle with the bandits has blown aside, but the excitement occasioned by the wonderful event has increased until it has gained a fever heat. The trains have brought hundreds of visitors to the scene of the bloody conflict between a desperate and notorious gang of experienced highwaymen and a brave and determined lot of citizens who had the nerve to preserve their rights and protect their property under the most trying circumstances.

The Dalton gang is no more, and travelers through the Indian Territory can go right along without fear now. The country, and the railroads and express companies especially, can breathe easier now that the Daltons are wiped out. The country is rid of the desperate gang, but the riddance cost Coffeyville some of its best blood.


The Eagles album “Desperado” was based on the Doolin-Dalton gang.

This video shows a Dalton gang hideout, their sister’s house in Meade Kansas. There is an escape tunnel that leads from the house to the barn. The gang kept their horses and gear in the barn, ready to exit the house unseen, and make a quick get-away.

I visited this place in 2009, and found it quite interesting. The proprietor/historian there also comes to Coffeyville yearly to participate in Coffeyville’s “Dalton Defender Days”, as a gunfighter in the annual shootout re-enactment. He and I spent probably an hour discussing the Dalton’s history.


Filed under AMERICANA, History, Kansas, Southeast Kansas, Trains

38 responses to “Coffeyville ~ THE DALTON’S LAST RAID

  1. Excellent post I really enjoyed reading this, I think you should post more like this. I think Kansas gets a bum rap because we only get associated with the Wizard of Oz. This state is rich in history that so often gets over looked. How many people actually remember that this state was Bonnie & Clydes’ stomping ground let alone the pioneering and western history? The history of this state still fascinates me.

    I’ve done my share of traveling and seen a lot of other places and things but I’m still proud to be a Kansan. Besides we’re the only people in the world who are crazy enough to climb up on our roofs to watch tornadoes.

    • I may be going this direction more….
      folks seem to like it!
      Also, I learn a hell of a lot about my own area.
      Strange how all the famous outlaws were either in or had connections to Quantrell’s Raiders.

      ‘The Outlaw Josie Wells’ should have just been a documentary.

      • I hope you do post more like this, that theme fits the title of the blog as it understates the history here and yet the painting of John Brown you’re using drives home the importance and role that Kansas played in history.

        Sad to say I probably slept through most of history in school so I really eat this stuff up now.

        Never take history 2nd hour.

    • I think Kansas gets a bum rap because we only get associated with the Wizard of Oz.

      It can’t be too bad to be associated with an important classic Hollywood film, can it?

      Although, being primarily associated with it can get old very quickly.

      Kansas is Sasnak backwards. Call me weird but I kind of like the sound of “sasnak” whether it be pronounced “sass-nack” or “saz-nack.”

      …let alone the pioneering and western history?

      Am I correct in being under the impression that when people think of the Old West, it’s not historically accurate to think of California, but rather it’s the Midwest?

      • I’m not sure what the historians say, but I always considered the old west as everything between the mississippi river and california.
        California was actually settled long before the old west was.

  2. Ann

    It looks like we’ve all got our very own Kelly gang. Love it Sekan . Keep going it’s great to hear your history. Also nothing wrong with the Wizard of Oz Briony’s school did that show one year and it was a huge success. Always did love sparkly shoes, now as I get older I like more sparkles. Sad aren’t I?

  3. Ann

    Gees Loon don’t you think that Dalton far right looks like Ivan Milat ? Ooooh scary!

  4. klaus

    Seriously, great stuff. Got hooked on The Long Riders back when, and this is great b/c it’s the real deal.

    Agree with Charles that KS gets a bum rap. A fascinating place is what I called it in your post on the African-American Regiment.

    Also agree with Charles: more like this. Really liked the post on the Osage, too. Didn’t comment so’s I didn’t sound like a groupie or something.

  5. In Ireland today we’ve got problems with gangs. Drug sellers all. It’s time we got to do here what was done to that Dalton gang.

    But given that over here citizens are not permitted to arm them selves; the gangs will continue to flourish and profit.

  6. A trip to Coffeville, back in 2003, led to a most interesting day: We stopped at the museum, only to find it closed. A gentleman walked up and asked if I’d ever been to it. I replied no, and had driven down from Joplin to enjoy it. He said he was the proprietor of it and invited me in. Mom decided to wait in the car and read: she was having problems walking for any length of time.

    I spent over two of the most informative hours I have spent anyplace there. He showed me things not on display(a ton of stuff); told me about the robbery; told me about Black Dog and his band of Osage Indians. I offered to pay him something for his trouble, but he refused. Said he didn’t do that too often, and missed doing it, and it was a fun way to spend the afternoon. Indeed it was.

  7. thg

    They would take us to that museum on field trips. That picture of them laid out on the sidewalk still pops into my nightmares occasionally.

  8. I’ve only read about a third of this entry, but I shall finish reading the rest on the morrow. So far, it’s a marvelous read. Action-packed and narratively taut.

  9. Tom Hook

    Really enjoyed this article! Seems the Charles Hook family of southeast KS.,spent time on both sides of the law as did the Daltons. In 1902, there was a shooting of Newton Carlisle in the northern part of Oklahoma Indian Territory, according to the Vinita Indian Chieftan. My great grandad and grandad were involved. Would love to get more details about this event e.g. what was the reason for the shooting.

  10. Jacqi

    I am distantly related to Richard Texas Jack Broadwell I find it interesting. Any other Broadwell relatives out there?

  11. When I was very young and used to hunt, my dad would take us to Northfield, Minnesota, where the James-Younger gang got shot to hell by a bunch of stoic Swedes. Note: Never mess with stoic Swedes (like in “Fargo”). Great post! Those guys were crazy.

  12. Hi Trace,
    Y’all ok over there in KS? Haven’t seen you in a few days.
    Fascinating article!

  13. Myra Maybelle Shirley might be one you could get into. Born in Carthage, Missouri, she became known as Belle Star, and led quite a life. Rumors abound of her running with people like Jesse James and the Youngers.

    You do this stuff so well, anyone reading your writings will be both educated and entertained. More, bro, more!!!!!

  14. Hmm, I swear I read this before 🙂 Great post Sekan enjoyed it as much the second time around 🙂

  15. Coffeyville CVB

    The Last Dalton Raid Reenactment will be September 30-October 1, 2011. in Coffeyville Kansas
    Reenactment is FREE to the public.
    Tour the Old Condon Bank, Death Alley, and the Dalton Defenders Museum.
    For more info visit

  16. I’d like to point out Grat Dalton never jumped out of a train window. He broke out of jail in Visalia and escaped before he was sentenced.

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  25. Charles Henderson

    Lived in Coffeyville For 16 years my best friend Don Keller and I would stop at the museum almost every day after Jr high and look thru the things on display

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