Railroads were open season for Oklahoma and Indian Territory outlaw gangs.

Glenn Shirley, the late historian of Oklahoma’s frontier history of lawmen and outlaws, said there were more stagecoach and train robberies in the Twin Territories than anywhere on the Western frontier. The first railroad to enter pre-state Oklahoma in 1871, was the Missouri, Kansas and Texas Railroad, known by the pioneers and locals as “The Katy.” The first Katy train robbery on record was committed by a band of Cherokees. It occurred some 10 miles north of the new Red River city of Denison, Texas, in the Choctaw Nation, during the summer of 1873. The bandits were said to have taken in a sum of $2,000 in cash plus a sizeable load of rings and watches from the passengers.

Train robberies in the Oklahoma and Indian territories got worse after 1890, when the Oklahoma Territory was formed. By that time, there were more railroads traversing the territories. In May 1891, the Dalton gang robbed an AT&SF (Santa Fe) Railroad train at Wharton, Oklahoma Territory, now Perry, Oklahoma. Bob Dalton and George Newcomb waited at the depot for the express to arrive. The rest of the gang waited at the stockyards. When the train pulled into the station, Dalton and Newcomb jumped into the cab of the steam engine with drawn guns and told the engineer to move the train to the stockyards and stop there. The engineer did as he was told. At the stockyards, the engineer and fireman were led to the express car and ordered to tell the express messenger to open the door. Shots were fired into the door and the messenger opened it. If passengers stuck their heads out of windows, the gang members would fire shots alongside the train. The Dalton gang was able to get two bags of money. Emmett Dalton later claimed the gang got $14,000 for the robbery.

The Daltons

In June of 1892, the Dalton gang robbed the Santa Fe Railroad at Red Rock, 15 miles north of Wharton, Oklahoma Territory. The Dalton gang learned there would be $75,000 in Indian annuity money transported via the Santa Fe on June 1. The Daltons had a well-known outlaw named Bill Doolin with them when they robbed this train. The gang was only able to open one of two safes in the messenger car and got no more than $11,000. After this robbery, a large contingent of lawmen were put in the field to find the Daltons but were unsuccessful. The Santa Fe Railroad offered $500 for the arrest of each member of the gang.

By this time, in the Twin Territories, it was reported that there were 11 men in the Dalton gang, including the brothers: Bob, Grat and Emmett Dalton. On Thursday night of July 14, 1892, the No. 2 Katy train was northbound when it made a stop at Adair in the Cherokee Nation, some 20 miles south of Vinita, Indian Territory, at around 9:42 p.m. The station agent was ordered at gunpoint to flag the train down. Two armed men quickly took command of the steam engine while the others took the conductor and trainmen in charge.

Unbeknownst to the outlaws, a posse was on board the train to protect it against robbers. The posse included railroad detective John J. Kinney, Deputy U.S. Marshal Sid Johnson, three members of the United States Indian Police, Captain Charles LeFlore, Alf McKay and Bud Kell. The posse stepped off the train to confront the robbers, and almost immediately Kinney, LeFlore and Johnson were wounded. The lawmen took refuge in a coal house. The outlaws used the trainmen as human shields during the gunfight. The lawmen stopped firing for fear of hitting one of the innocent workmen.

Meanwhile, other members of the gang were pouring a steady stream of gunfire into the express car. The messenger opened the door and gave the robbers access to the car. The robbers looted the safe in the express car for $17,000, but were not successful in getting the station agent to open the safe in the station. While riding out of town, the gang shot two unarmed doctors sitting outside the drug store. Dr. D. L. Goff died from his gunshot, and Dr. T.S. Youngblood lost a foot to his gun wound. After this robbery, the Katy Railroad placed a $5,000 reward for each member of the gang, which included the Dalton Brothers, Dick Broadwell, Charlie Pierce, Bill Doolin and William Power.

Open Season on Trains

A second train robbery happened at Wharton on September 8, 1892. Five men held up the train, captured the express car, opened the safe and found nothing worth taking. They left with two baskets of grapes. There was a third train robbery at Wharton on November 8, 1892. Three white men held up a Santa Fe southbound passenger train. Robbers only got a few small packages and took the messengers’ Winchester rifle and revolvers. In January of 1893, two of the robbers, Jesse Jackson and Scott Bruner were captured after having a running gunfight with a posse led by Black Deputy U.S. Marshals Rufus Cannon and Ike Rogers. At close range, Cannon shotgunned off one of Jackson’s arms during the gunfight. The outlaws were turned over to Deputy U.S. Marshal Heck Thomas in Bartlesville, I.T. Another man in custody named Ernest Lewis turned state’s evidence and testified about the robbery to authorities.

On October 20, 1894, a Missouri Pacific Railroad passenger train was robbed at Coretta, Creek Nation, now Okay, Oklahoma, five miles south of the town of Wagoner. A gang member threw a siding switch while the train was going about 25 miles an hour. The train went into the siding and ran into some box cars on the track. The rob-bers were able to loot the “local” safe in the express
car but couldn’t open the “through” safe. The pass-engers were robbed of their money and valuables as the robbers went through the coach cars. The bandits shot out every window in the train and even the steam gauge and gauge pump in the locomotive. Black Creek Freedman outlaw Buss Luckey and his all-Black gang comprised of Bob Elzey, and brothers Frank, Henry and Will Smith carried out the robbery.

Texas Jack

Katy’s premier passenger train, the northbound Katy Flyer, was robbed on the night of November 13, 1894. The leader was a White man named Nathaniel “Texas Jack” Reed with three tough Black desperadoes: Buss Luckey, Tom Root and Will Smith. The robbery took place at Blackstone Switch, near Wybark, eight miles north of Muskogee, Indian Territory. Again, the outlaws switched the train to a siding from the mainline. Riding as guards in the express car were lawmen Bud Ledbetter and Paden Tolbert, legendary lawmen of the Indian Territory. In the express car was $60,000 in gold bullion and silver. A furious gunbattle ensued, and the outlaws made no progress in capturing the express car. While the gunfight was taking place, Texas Jack went through the chair car and robbed the passengers of $460, eight watches and three pistols.

On leaving the scene, Ledbetter shot Texas Jack with his Winchester and seriously wounded him. Buss Luckey picked up Jack, and the outlaws made a quick escape on horseback. Luckey was later captured by authorities and convicted by testimony from Root, who turned state’s evidence. Root was later killed in a gunfight; Smith was never captured. In Arkansas, Reed turned himself in and Judge Isaac C. Parker gave him a five-year sentence. When released, Reed became an evangelist and traveled in Wild West shows.

A southbound Rock Island Railroad passenger train was robbed on April 3, 1895, in the Oklahoma Territory. A group of five men led by William “Tulsa Jack” Blake and Red Buck Weightman forced their way aboard and robbed the express car of $400. They also stole jewelry and high-valued watches from panic-stricken passengers whom they threatened to shoot if they offered any resistance. The outlaws were able to get away, but Blake and Weightman were both killed later by deputy U.S. marshals in the Oklahoma Territory.

Al Jennings

On August 16, 1897, lawyer turned outlaw Al Jennings had assembled a gang that included two hardcases from the Bill Doolin gang: Little Dick West and Dynamite Dick Clifton. They decided to rob the Santa Fe passenger train at Edmond, Oklahoma Territory. The outlaws were able to get aboard the engine and ordered the engineer to stop the train. The gang tried unsuccessfully to blow the safe in the baggage car, so they robbed the passengers of their valuables. The gang rode east toward the Indian Territory and were seen by Black farmers near the town of Arcadia. Deputy U.S. Marshal Bud Ledbetter later caught Al Jennings in the Creek Nation. Jennings was convicted and sent to prison. Later, West and Clifton were both killed by federal lawmen in the territories.

This is just a recap of a few of the train robberies in the Oklahoma and Indian Territories during the frontier era. A train ticket in the Twin Territories could be very exciting and unpredictable­­—as well as deadly and dangerous.