SAN LUIS VALLEY — Now, Billy LeRoy was not your typical looking criminal. The young highwayman was known for dressing on the up-scale side and one of his most infamous traits that kept lawmen guessing who he was, was his size four shoe.
At many of the locations where LeRoy held up a train or stagecoach, lawmen would find footprints of his size four shoe and were often, convinced that these criminal acts of theft were done by a woman. This fact and many others kept local lawmen confused and wondering who might be responsible for the countless robberies that were taking place.
After his night of drinking and losing horribly while gambling, Billy LeRoy decided to head out and get some of his money back in the best, sure way he knew how, holding up a stagecoach. LeRoy used the last bit of his money to rent a horse and headed West along the Rio Grande River toward Del Norte. LeRoy found a place on the stagecoach route that was surrounded by sagebrush and having secured his location in the dead of night, placed cowboy hats on top of several bushes and placed wooden rifles below the hats. His stage was set.
Finally, after hours of waiting, the Barlow Sanderson Stage made its way up the road just before dawn and found a large wooden fence post laying in their path. The stage stopped and LeRoy stepped out from his hiding place and ordered the stage handler to toss him the mail bag as well as the leather envelope that contained a decent amount of money declaring that they were surrounded and should just follow directions. The stage handler complied while LeRoy demanded that the passengers also throw down their money and jewelry. LeRoy, being satisfied with his haul, let the stage continue. No one was hurt during the raid.
The following day, LeRoy left the San Luis Valley again and headed to Pueblo where he was recognized by a postal inspector and thrown in jail. US Commissioner Andrew Brazee charged LeRoy with two counts of stagecoach robbery and set his bail at $7,000. LeRoy, eager to take responsibility for his crimes, gave a full confession of his adventures and criminal activity in Colorado. LeRoy attempted to escape with two other prisoners who were shot during the escape and was put back in jail to await charges for a third robbery in the San Luis Valley.
LeRoy was placed on a train after being sentenced to 10 years in the House of Corrections located in Detroit, Mich. As the train neared its destination, LeRoy stole a piece of wire and used it to escape from his handcuffs. LeRoy jumped from the train when his captor went to the restroom and made his way to Hays City, Kan. Where he hid under the porch of an abandoned house for three days. According to reports, he survived off a single ear of corn during that time.
After LeRoy felt it safe to move again, he headed back home to Indianapolis where he met up with his brother Silas. Billy told his brother about his crimes and hauls in the San Luis Valley and the two decided it was worth it to go back and see how much they could get. It was at this time that Silas adopted the alias Sam Potter and between him and Billy they gathered a band of men that consisted of Tom O’Phallin, Jim Wilson, and Dave Rudenbaugh. Billy was the leader of the band.
Their first attempt to rob a stagecoach after returning to the San Luis Valley went horribly wrong. When the band of men stepped out to stop a western-bound coach led by Jack Wells, they startled the horses and seeing a chance to get away, the driver grabbed the reins, turned the stagecoach into the bushes and escaped under a hail of bullets. Luckily, no one was hurt during the incident.
Their next attempt went just as wrong as the first but this time, when they opened fire on the stagecoach driven by Joe McCormick, the passenger, an engineer for the Denver and Rio Grande Railroad grabbed his shotgun and caught one of the other passengers in the leg. LeRoy boarded the stagecoach and made away with five bags of mail and $118. He also took the shotgun from the engineer.
By this time, lawmen throughout the area were hot on their tail and the band of thieves and local vigilantes began to gain interest. Money was pooled together from citizens of the San Luis Valley to help fund the effort to put these men in jail. The band of thieves hunkered down in a location near North Clear Creek by Creede and it was there that a group of citizens took all five men into custody.
All of the men were taken without incident except LeRoy. Seeing that the gig was up, LeRoy pulled his pistol to make his stand when he decided it would be better for him to run. After taking flight, one of the lawmen fired and shot LeRoy in the leg and took him into custody. The band of thieves were transported to Del Norte to await trial and it was there that citizens took matters into their own hands.
Once the prisoners were secured in the jail, over 100 masked men raided the jailhouse and took LeRoy and his brother Sam Potter to a nearby tree where they were hung for their crimes. Billy LeRoy’s last words before the noose was hung about his neck rang out in the night while his brother sobbed beside him, “I have waltzed through the region a long time without paying the fiddler, so now gentleman I am ready to meet the cashier. Go on with your cart.” The posse of vigilantes did just that and whipped the horses in front of the cart that held LeRoy and his brother ending the Colorado Highwaymen’s lives once and for all.
For more information or to find stories such as this visit the Rio Grande County Museum in Del Norte.