Editor’s Note: Part one of a two-part series

SAN LUIS VALLEY — The San Luis Valley has a rich history dating back to the early 1800s thanks to the many characters that lived rough and tumble lives in the great West. Lawlessness was a way of life for many in those early days and like the song by Jim Croce, “Bad, Bad Leroy Brown” the San Luis Valley had a bad, bad LeRoy of its own.

According to accounts provided by the Rio Grande County Museum, this story begins with a troubled youth that would grow into a famous, well-known outlaw that was a bad as they came. The LeRoy Brothers also known as the Colorado Highwaymen, dates to the late-1800s when a young lad by the name of William Pond whose alias later became Billy LeRoy. LeRoy was also known as Billy the Kid, Colorado Highwayman, Sam Pond or Sam Potter. 

No matter which name he was using at the time, Billy LeRoy grew up in Indianapolis, Ind. During his childhood, Billy was a neighborhood nuisance. He was the first to raid neighborhood hen roosts and orchards according to a historical account of Billy’s life written by a local historian. 

After developing a taste for a life of crime, Billy quickly moved from bothering his neighborhood to a juvenile outlaw. Many who recounted Billy’s younger years often said they wished he would do time in prison or even become what they referred to as a “juvenile angel,” meaning they wanted him dead. All of this sent Billy down a road that ultimately led him and his brother to an early death. 

Billy came to the San Luis Valley after a strange and wavering path. Once Indianapolis law enforcement had it out to arrest of Billy, he decided it was high time to hit the rails and head West, where he planned to become a famous outlaw. Billy was arrested by law enforcement in Indianapolis but weaseled out of the handcuffs that held him and escaped by jumping out of a two-story window. 

On his way to Colorado, Billy encountered several hardened criminals that not only helped him reach his destination, but also taught him the ins and outs of a life of crime. During his trek heading West, Billy met an unsavory character who named himself California Bill also known as William Miner. Miner lit a spark inside Billy and taught him the fundamentals of theft and later the two stopped the Alpine-Gunnison stage but only got away with $50 in cash. 

The next stage the two robbed was on Slumgullion Pass on Oct. 7, 1880 and this time, they made out with $100 which back then was quite an accomplishment. Back in these days, many of the roads we travel today began as stagecoach routes. Trains had yet to make a huge impact on communities like those in the San Luis Valley. 

Only one week later, Billy and his partner in crime the infamous California Bill first showed their faces in the San Luis Valley robbing the stage between Alamosa and Del Norte. It was during this robbery that Billy made a name for himself and was now a wanted man. The two made out with $4,000 in cash and other priceless trinkets. It was at this time that the two split ways and Billy, knowing the law was hot on his tail headed back East to Chicago after a brief stop in Pueblo. 

It wasn’t long before Billy made his way back to Denver and then eventually back to the San Luis Valley. Billy had a bad habit of gambling that resulted in trouble for the young lad more than once. Billy moseyed his way back to Alamosa and headed straight to a local gambling fraternity. The local population consisted of the western characters we have all come to know and love; many of which would see a sharp young man like Billy and take advantage of them as often as they could. 

During his stay in Alamosa and through a rough night of gambling, Billy was taken for all he was worth, which wasn’t much at the time. Billy ended up spending the night drinking heavily and woke the next morning hungover and broke. This was in early January of 1881, barely a year after Billy had adopted his life of hard crime. What he chose to do next would shape the end for the young Colorado Highwayman.