Once A Drug Buster, Now A Prominent Critic Of The 'War On Drugs'

When he's hiring new deputies, the test is simple. The sheriff asks them to write their life stories. "Most of this job is writing," Bill Masters says. "If they can't write, they're a constant pain in the ass." So if Masters wrote his own life story, what would he write?

Masters grew up a straight-laced kid in L.A., joined the Coast Guard, kicked around and decided he didn't want to go back to L.A. It was hot there, and you had to wear a tie to job interviews. So he said screw this, "I'm going to Telluride and go ski for a year."

He was a liftie who helped build Lift 7. Then fate intervened. Driving down valley, a rock careened down the hill and smashed the top of his Volkswagen Bug. Crushed the roof. Crushed the groceries. So he hitchhiked. One day, the Telluride Marshal picked him up, and offered him a job. Masters was only 23 years old.

Shortly thereafter, he was named Sheriff. He got along well with the old miners, though they occasionally stole the lights off the top of his cop car and joyrided it down the street. The hippies were less tolerant of the new, short-haired, rednecky sheriff. Telluride was a famous drug spot, and Masters was determined to clean it up. He set up an elaborate sting involving all kinds of Dragnet devices -- wiretapping, undercover police officers, and he arrested some druggies/town board members.

I thought we could arrest our way out of this problem," Masters says.

Pro-druggers organized a party and burned Masters in effigy. Sky Walters, now the undersheriff, worried they'd burn him in person. Masters thought he'd never get re-elected sheriff. Since then, he's won seven elections.

Since those early anti-drug days, Masters has changed his thinking, changed his party -- from Republican to Libertarian, and now to Democrat -- and become one of America's most outspoken and honest critics of the War on Drugs. His 2001 book, "Drug War Addiction," argues that police departments are addicted to the money they get for the War on Drugs, despite all the damage it does to otherwise decent people. He talks about wrestling down heroin addicts with his wife Jill, a paramedic and now a town council member. He also edited a book called "The New Prohibition," which includes Ron Paul and Jesse Ventura. It was well reviewed.

Sheriff of a small county, Masters doesn't make bank. In the old days, for dough, he worked at a gas station. Now, he co-owns an alarm company and works security for the family of Tom Cruise, whom Masters calls "a great guy, great family." Masters, 57, plans to run for sheriff again in 2010. "What else would I do?" Masters laughs. "I'm completely unskilled."

When you write it down on paper, his life story says otherwise.

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