July 15, 1892

The Dalton Gang vs Katy Railroad Guards

The Last Successful Raid of the Daltons Turns Tragic 

The Dalton Gang’s triumph is short-lived. Illustrations by Bob Boze Bell/Photos True West Archives/Maps by Gus Walker


Riding eight strong, the Dalton Gang enters Adair, Indian Territory (present-day Oklahoma). They com-mandeer the train station, preparing to pilfer Katy Train No. 2 (a Missouri, Kansas & Texas passenger train). When the train glides into the station at 9:42 p.m., the gang boards, capturing members of the train crew without incident and telling them to obey or “have their brains blown out.”

As the crew is marched down to the express car, one of the gang members begins shooting toward the town, evidently trying to discourage  towns-people from getting any ideas about joining the party.


Dead Men Riding – Eight outlaws ride toward Adair, Oklahoma. In addition to their daredevil ways, they share one commonality: All of them will stop a hail of bullets, but only one will live to tell about it. The robbers are believed to have been Bob, Grat (just escaped from jail in California) and Emmett Dalton, Bill Doolin, Bill Power, Dick Broadwell, Charley Pierce and Bitter Creek Newcomb.

After some resistance, the outlaws break into the express car and force the fireman and the messenger to open the through safe (which contains little loot). The gang then rifles through the car and loads the collected money into a stolen spring wagon. (Although the exact amount taken is unknown, most historians estimate the take at about $17,000.)

As the robbers load up, Winchester slugs begin whipping very close to the heads of the outlaws. Eight train guards, including lawmen J.J. Kinney and Capt. J.H. LeFlore, are shooting out the windows of the smoking car and at the gang. 

With the firing increasing, the lawmen get off the train and “fort up” in a coal house next to the tracks. The lawmen pour a heavy fire at the crowd around the express car. The robbers use their hostages as shields while they shoot into the wood building. 


The outlaws, including Bob Dalton, send a withering fire into the coal shed where the railroad guards have forted up. Accurate, pinpoint firing knocks them out of the fight.


Within moments, three of the lawmen inside are hit and knocked out of the fight. The July 21 Indian Chieftain reported the casualties: “A bullet went through the flesh of Mr. Kinney’s shoulder, another struck Johnson’s watch and imbedded itself in his arm, while Charley Leflore [sic] had the stock of his gun struck with a shot and the slivers driven into his arm.” 

Gang member Charley Pierce finally shows up with the horses. While one outlaw returns fire at the guards, the others mount up and clatter down the streets of the small town, sending about 20 shots at two men sitting in front of the Skinner Drug Store. Both bystanders are doctors—Dr. W.L. Goff is mortally wounded; Dr. T.S. Youngblood will lose part of his right foot. (Gang apologists later claim the two men were shot by errant bullets fired by the train guards, yet it is more likely the men were hit by outlaw bullets.) 

The gang’s last successful raid is over, but their lawless run is rapidly coming to a violent end.


As the gang rides through the town after the robbery, the outlaws fire shots at bystanders. The promiscuous bullets strike two doctors. With the subsequent death of one of them, Dr. Goff (he lived for three days), rewards for the gang reach $40,000.



Deadly Daltons’ Deadhead 

After a flurry of robberies in the Indian Territory (see map, above), Bob Dalton and his gang planned on hitting Red Rock Station. When the gang got into position at 10:30 p.m. on June 1, Bob didn’t like the look of the darkened smoking car as the train pulled into the small, one-horse station. 

Bob sensed that the train carried a car full of loaded Winchesters. Bob’s suspicion turned out to be correct. Inside were Wells Fargo detective Fred Dodge and the formidable U.S. Deputy Marshal Heck Thomas, among others. 

Letting that train depart, the gang stood by. Soon enough, an un-escorted express train arrived, and the gang moved in for the kill. When the gang strong-armed their way into the car, they unfortunately found little money. The big money had gone through with the first train. The chagrined gang took what was there (less than $3,000) and then mugged a train employee of his gold watch and pocket cash, and, probably just for spite, took the crew’s lunchboxes.

The gang scattered to confuse pursuit but regrouped at one of their favorite caves, supposedly near Tulsa. There, they discussed raiding the Katy Train at Pryor Creek. But Bob, who noticed an Indian farmer had spotted them and worried the man would alert the authorities, thought it’d be wise to hit the Katy train at the Adair station instead. The others agreed. 

Although the raid in Adair would end up a success, time was running out for the gang.


Bob Dalton, in desperation, had one more job planned. It would prove to be his last. He fooled nobody with the fake whiskers.


The Best in the Business

By the time of the train robbery in Adair, the Daltons are already being chased by some of the best lawmen in the business, including Wells Fargo Detective Fred Dodge and Deputy U.S. Marshals Heck Thomas and Chris Madsen.

J.J. Kinney, special detective of the railroad, and Capt. J.H. LeFlore, chief of the Cherokee Indian Police, discover the Daltons by chance, when the gang members board the Adair train.

On July 21, 1892, the Indian Chieftain re-ported the robbery, stating that once the guards became aware of the robbery, they opened fire at the outlaws through the car windows; the robbers responded in kind.

The article also stated, “The railroad and express companies have joined in an offer of $5,000 each ‘for conviction, the aggregate sum not to exceed $40,000.’ Under these terms there will be no pursuit by men of experience in the country. Those who know the Dalton boys, and there can be no doubt but that they were in this hold-up [sic], know they cannot be captured alive. To kill them does not comply with the terms and will not secure the reward but it will expose whoever does to prosecution in the U.S. Court in Fort Smith.”


“Nemesis” is what Emmett Dalton called Deputy Marshal Heck Thomas (seated front row, at left). Many believe Thomas’ dogged pursuit caused Emmett’s brother Bob to attack Coffeyville hastily and contributed directly to the gang’s demise. Wells Fargo certainly agreed: “We feel that your work, more than anything, brought about the extermination of this gang … and are happy to hand you, from our railway and express pool, a check herewith in the amount of $1,500.”


And Then There Were Five

With several posses less than 24 hours behind and closing in, Bob Dalton makes a hasty plan and the gang heads north to Coffeyville, Kansas. On this raid, there are only five members—the three Dalton brothers, Bill Power and Dick Broadwell.

 Not invited, or perhaps declining, are outlaw stalwarts Bill Doolin, Bitter Creek Newcomb and Charley Pierce. Some believe Doolin actually does go along but drops out at the last minute because his horse comes up lame or perhaps he has a brief moment of clarity. Others speculate Bob wants all the glory for the outrageous double heist (besides, the split would be sweeter). In any case, the other members of the so-called Dalton Gang do not have long to run.


(From left) Bill Power, Bob Dalton, Grat Dalton and Dick Broadwell


Aftermath: Odds & Ends

From their hideout near Tulsa, the Daltons, along with Bill Power and Dick Broadwell, headed for their historic, and disastrous, fate in Coffeyville, Kansas, where they tried to rob two banks (see Classic Gunfights Vol. I).

The only survivor, Emmett Dalton, served 14 years and lived out his life in California where he became somewhat of a celebrity. The rest of the gang met a more grisly end. 


Emmett Dalton


Recommended:  Daltons! The Raid on Coffeyville, Kansas by Robert Barr Smith, published by University of Oklahoma Press; Shoot from the Lip by Nancy B. Samuelson, published by Shooting Star Press; and Captain Jack and the Dalton Gang by John J. Kinney, published by University Press of Kansas.

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