The candidate in question was Joe Edwards, a 29-year-old lawyer who had gained some notoriety the year before when he defended a group of hippies who'd been arrested for "vagrancy" in town. Edwards argued that the arrests were part of a pattern of institutional bias in Aspen wherein those who looked different were hassled by the local police force and its magistrate, Guido Meyer. He challenged Meyer's "unconstitutional" sentencing of beatniks and eventually had him removed from office.

Thompson's plan was to run Edwards as a candidate for mayor, but as the campaign progressed and it started to look like Edwards might actually win, it occurred to him that he himself could run for sheriff and do his own part toward reforming local politics:

The Old Guard was doomed, the liberals were terrorized, and the Underground had emerged, with terrible suddenness, on a very serious power trip. Throughout the campaign I'd been promising, on the streets and in the bars, that if Edwards won this Mayor's race I would run for Sheriff next year (November, 1970) … but it never occurred to me that I would have to actually run; no more than I'd ever seriously believed we could mount a "takeover bid" in Aspen.

Edwards eventually lost by six votes, but Thompson was galvanized to continue with his campaign, and the result was "one of Hunter's greatest times," as a friend later recalled. His campaign symbol was "a double-thumbed fist, clutching a peyote button" superimposed on a sheriff's star, which was featured on posters around town. His platform, detailed in Rolling Stone, called for the streets of Aspen to be ripped up with jackhammers and for the creation of "a huge parking and auto-storage lot on the outskirts of town," as well as for the town's name to be changed to "Fat City" in an effort to deter the "greed heads, land-rapers, and other human jackals from capitalizing on the name 'Aspen.'"

And, perhaps predictably, he proposed a relaxed policy for drug offenses, even as he noted that "any sheriff of any county in Colorado is legally responsible for enforcing all state laws regarding drugs—even those few he might personally disagree with." Thompson's caveat was that dishonest drug dealers should be set in stocks on the courthouse lawn, and that "it will be the general philosophy of the Sheriff's office that no drug worth taking should be sold for money."

During the campaign, Thompson shaved his head in order to be able to refer to the incumbent Republican Carrol D. Whitmire, who had a crew cut, as "my long-haired opponent." He wore Converse All-Stars and shorts to town hall meetings, where he spoke with surprising seriousness about the environment and the "silly" laws against marijuana. He made a campaign video that showed him riding a motorcycle through the mountains while his friend, writer James Salter, narrated an endorsement:

Hunter represents something wholly alien to the other candidates for Sheriff: ideas. And, a sympathy towards the young, generous, grass-oriented society which is making the only serious effort to face the technological nightmare we've created. The only thing against him is, he's a visionary. He wants too pure a world.

Thompson lost the election by 173 votes to his opponent's 204 and promptly quit politics, which is a shame because the "Fat City Ideas Festival" really has a nice ring to it. But his spirit lingers: Recreational marijuana was legalized in Colorado by state ballot in 2012.

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