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Willoughby: Banks and train robbers

Tim Willoughby
Legends & Legacies
Photo of Oliver Curtis Berry, the "Empire State Train Robber," taken in 1892.
Library of Congress

We think of the early days of Aspen as well past the “Wild West” period, but, in 1892, bank and train robbers flooded the news. Today’s media sticks to the newspaper adage “if it bleeds it leads,” titillating viewers’ fascination for crime. Today, we focus on cartels and street gangs, and, in 1892, the Dalton Gang’s two-year trail of deadly robberies satisfied readers’ fascination and stoked their fears.

The year of criminal attention began with Oliver Curtis Perry, known as the Empire State Train Robber — and because of his height, also as the “small train robber.” He attracted Aspen’s attention from his notoriety in Butte, Montana, and for robbing trains in New York. He was caught and convicted at the age of 26.

As you might expect, that kind of behavior was dominated by younger people. The Dalton Gang members, eight of them including four Dalton brothers, were all under that age, two of them teenagers. Their bank and train robberies lasted two years, from 1890 to 1892.



Their entry into crime had an unusual beginning. Three of the brothers worked for the courts in Arkansas and the Osage Nation. They served notices and served on possies. The problem was they were not on a salary, so they needed money between assignments. They intercepted bootleggers taking booze to the Indian reservation, confiscated the alcohol, and sold it on their own. That led to stealing Indian horses.

When their skullduggery became evident, they went to California, and, after drunken altercations, they had to flee and took to robbing trains and banks in New Mexico, Kansas, Oklahoma, and Indian Territory.




In the fall of 1891, a marshal and a California detective accompanied by a party of Indians cornered the Dalton Gang. The gang sent a note saying to “go away and let them alone — they would kill every man attempting to capture them.” They left and robbed another train taking somewhere between $50,000 and $75,000 in Kansas. Two gang members crawled into the engine, forced the engineer to stop and blew open the safe. They wounded four people, and one died from a stray bullet.

In early September, a deputy marshal telegraphed he had captured the five Daltons, but he disappeared. Later that month, a pool of money was offered as a reward — $22,000. The marshal re-emerged: He had captured two, and others escaped.

The finale was an attempt to rob two banks at the same time in Coffeyville, Kansas. Later, it was revealed that the leader, Bob Dalton, wanted to do the robbery in broad daylight and rob two banks to outdo two other notorious gangs of that time. Doing two banks took time, giving locals time to organize to stop the robbery. A shootout resulted in eight deaths: four gang members, four locals. Two gang members were wounded and escaped.

Emmet Dalton, still a teenager and one of those who escaped, was later captured and tried for murder. He was convicted but always said he did not kill anyone.

In 1907, Aspen read in the paper that he had been paroled to address severe medical conditions.

Also in 1892, the Aspen Daily Times printed an interview with a local who was on a train carrying the wife of a notorious gang leader on its trip from San Francisco to St Louis. The wife, already convicted, was going to testify against her husband. The car was fortified, had eight guards in the car with her, and a sprinkling of Pinkerton men on other cars.

You might think train robbers would have attempted to rob a train of Aspen’s silver ore, but they could not haul much of their heist away on their horses. Most of the train robberies were thefts from safes with currency, especially gold.

Aspen banks were in greater danger, especially on days when payroll would be paid to hundreds of miners. Two major banks, one in the Wheeler and the other in the Cowenhoven Building, had large safes with very thick doors. Even though Aspen stored tons of dynamite, no one ever tried to blast into either of them. But, readers of the papers, like those of today getting their daily dose of scary crime stories, could imagine bank and train robberies leaving them worried about their safety.

Tim Willoughby’s family story parallels Aspen’s. He began sharing folklore while teaching at Aspen Country Day School and Colorado Mountain College. Now a tourist in his native town, he views it with historical perspective. Reach him at redmtn2@comcast.net.

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