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Willoughby: Banks and train robbers

Oliver Curtis Berry’s “Empire State Train Robber” photo taken in 1892.
Library of Congress

We think of Aspen’s early days and the “Wild West” era, but in 1892, bank and railroad robbers flooded the news. Today’s mass media follow the “blood leads” newspaper adage that weakens the audience’s fascination with crime. Today, we focus on cartels and street gangs, and in 1892, two years of deadly robberies by the Dalton Gang satisfy readers’ fascination and stoke their fears.

The Year in Crime Focus began with Oliver Curtis Perry, known as the Empire State Train Robber and also known as the “Little Train Robber” because of his height. He attracted Aspen’s attention from his reputation in Butte, Montana, and from robbing trains in New York. He was arrested and sentenced at the age of 26.

As you might expect, such behavior was dominated by young people. The members of the Dalton Gang, eight of them including the four Dalton brothers, were all under that age, two of them minors. Their bank and railroad robberies lasted for two years from 1890 to 1892.



Their foray into crime had an unusual beginning. Three of the brothers served on the courts of Arkansas and the Osage Nation. They presented advertisements and served on positions. The problem was that they were not on salary, so they needed money between assignments. They hijacked bootleggers who were taking them to Indian reservations and took the alcohol and sold it themselves. This led to the stealing of Indian horses.

When their skulls were revealed, they went to California, and after a drunken brawl, they had to flee and rob trains and banks in New Mexico, Kansas, Oklahoma, and Indian Territory.



In the year In late 1891, a marshal and a California detective, along with a group of Indians, cornered the Dalton Gang. The gang sent a note saying, “Go away and leave them – they will kill anyone who tries to catch them.” They went and robbed another train in Kansas that took $50,000 to $75,000. Two gang members broke into the engine, forced the engineer to stop and blew the safe. They injured four people, one of whom was shot dead.

In early September, a deputy marshal telegraphed that the five Daltons had been arrested but disappeared. Later that month, a prize money was offered – $22,000. The marshal reappears, marking the two and the others escaping.

It ended up being an attempted robbery of two banks in Coffeyville, Kansas at the same time. It was later discovered that the ringleader, Bob Dalton, had planned to carry out the robbery in broad daylight and rob two banks. It took time to make two banks, which gave the local residents time to organize to stop the robbery. Eight people died in the shooting. Four gang members, four locals. Two gang members were injured and escaped.

Emmett Dalton, still a teenager and one of the escapees, was later arrested and charged with murder. He was convicted, but he always said that he did not kill anyone.

In the year In 1907, he read in the newspaper that Aspen had been paroled for serious health problems.

Also in 1892 Aspen Daily Times He published an interview with a local man who was on a train from San Francisco to St. Louis with the wife of a notorious gang leader. An ex-convict wife was about to testify against her husband. The car was fortified, he had eight guards in the car, and Pinkerton’s men were spraying other cars.

You might think that train robbers would try to rob Aspen’s silver mines by train, but they couldn’t pull much of their baggage on their horses. Most train robberies involve looting of cash, especially gold.

Aspen’s banks were more at risk, especially on paydays for hundreds of miners. Two large banks, one in the Wheeler and the other in the Cowenhoven building, had large vaults with thick doors. Although Aspen had stockpiled tons of dynamite, neither of them tried to detonate it. But, readers of the newspapers, like today’s who get their daily horror stories of crime, can imagine that bank and train robberies would make them worry about their safety.

Tim Willoughby’s family history parallels that of Aspen. He began sharing folklore while teaching at Aspen Country Day School and Colorado Mountain College. Now the hometown tourist sees it from a historical perspective. Access it at redmtn2@comcast.net.

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