The longest-tenured – and most internet-famous – sheriff in Colorado is retiring later this year.
Bill Masters has served as the sheriff in San Miguel County for 45 years and as a peace officer for 50. In recent years, his office has gained viral fame for social media posts about “ass clowns”driving up a dangerous mountain pass near Telluride and an famous “large boulder the size of a small boulder."
On Thursday, he announced his plans to step down from the post this June. For Masters, it’s a “bittersweet” decision.
“Being the San Miguel County sheriff is probably the greatest job on Earth,” he told Denver7 on a zoom call in the hours after the announcement went public. “It's a great County. It's got great people.”
At the same time, though, he said the job used to be “a lot more fun than it is now” thanks in part to the political and societal attitudes toward policing. He hopes his successor is someone younger with “more patience” for today’s climate.
“I hope [it’s someone] that maybe can adjust better than an old, grumpy police officer. I don't want to be that person, and I'm kind of getting that way,” Masters said. “I hope it's a young person that can understand what the community really needs and wants.”
Humble beginnings to a long career
Masters grew up in California and moved to Colorado in 1974, with about $20 in his pocket and his sights set on a job at Telluride Ski Resort, which had just opened two years earlier, or at the active mine there.
“The last thing on my mind is that I was going to be a peace officer in this small town,” he recalled.
But that all changed after a night of drinking at one of the local bars a few months later. He was hitchhiking home when the town marshal gave him a ride. As it turned out, Masters had a degree in criminal justice and the town marshal’s office needed a deputy.
“So he hired me as the kind of Barney Fife in Mayberry, and that's how I started my career here,” he said.
He would become the chief marshal shortly thereafter and was appointed sheriff at the age of 27. Thanks to support from his staff and the community – and no term limits for elected officials in San Miguel County – Masters has been re-elected 12 times.
Five decades of change
When Masters moved there in the mid-1970s, Telluride was a small, unassuming mining town with muddy roads and a newly-founded ski area that was struggling. There was no mountain village and no airport. Masters bought a house for $36,000.
Fast forward a half-century and private jets bring wealthy travelers to what was just named the most expensive and luxurious ski town in the United States. The median home sale price is $3.2 million, according to Realtor.com.
The skyrocketing prices in the area has made it difficult to recruit police officers, Masters said. He is one of just two sheriff’s office employees who still lives in town, with some of his staff members commuting as much as 70 miles from Montrose.
Masters laments the challenges posed by the cost of living, but what upsets him more is the immense change to policing laws in Colorado and the national attitude toward law enforcement.
- Hear our full conversation with Bill Masters in the video player below:
He points specifically to Senate Bill 217, the police accountability bill passed during the 2020 legislative session and addresses everything from body-worn cameras to data collection to the liability of officers when excessive force is used.
“I haven’t been sued in 50 years, and in the past three years, I've been sued four times, and all because of this new law,” he said. “And that's wrong. There's something really flawed with it.”
It’s one of the reasons he decided to retire.
“I find [it] hard to adjust to these new changes,” he said.
Masters said there’s more pressure than ever on officers from both sides of the political aisle, adding another challenge to recruitment efforts.
“I've never been in a situation before when both sides of the political spectrum say they support police officers, but they talk the talk [and] don't walk the walk,” he said. “And that's really upsetting.”
We also talked about the San Miguel Sheriff’s viral fame
It was just over five years ago that a road closure on Highway 145 gained widespread internet fame. A 10,000-pound rock had fallen into the middle of the road.
The sheriff’s office warned followers on social media that “a large boulder the size of a small boulder” was blocking the eastbound lanes.
The viral sensation, it turns out, was the result of a typo. Public information officer Susan Lilly meant to say the boulder was the size of a small car.
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But the San Miguel Sheriff has made waves online with blunt remarks in the years since. In 2023, Masters called out the “ass clowns” who were attempting to drive over the dangerous Black Bear Pass. Last year, his office was looking for the “loser” who strung wires across a hiking trail. It’s a unique approach to transparency.
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“I have found that every single one of our difficult cases has been solved by social media, by your media, by television, getting the information out to the public, and in turn getting the public to call us,” he said. “So I am a big fan of having a transparent office and having the media in all forms right there at my fingertips to be able to get our information out to them.”
“I hope that I pass that on to the future sheriff.”
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