Hunter S. Thompson Ran for Sheriff on a ‘Free Weed’ Platform—and Almost Won

Published on May 13, 2019 · Last updated July 28, 2020

Santa Cruz, California is a small town about 70 miles south of San Francisco best known for its killer cold-water surf break, the quality of the local cannabis, and a University of California campus with a longstanding counterculture reputation.

Since 2008, UC Santa Cruz has been home to the official Grateful Dead archives (donated by the band). And now the Special Collections department at UCSC’s McHenry Library hosts a new archive of rare materials related to legendary Gonzo journalist Hunter S. Thompson.

The Hunter Thompson archive was donated by Eric Shoaf, dean of the academic library at Queens University in Charlotte. Shoaf amassed his collection while compiling Gonzology, an HST bibliography that he published last year. Anyone who’s interested can simply show up at McHenry Library during operating hours and make a request to see anything in the collection. (While you wait for them to pull your materials, head downstairs and check out a small Grateful Dead museum, where artifacts ranging from old concert tickets to formal meeting notes are artfully displayed.)

Personally, I’ve long been fascinated by Hunter Thompson, so it was a sincere thrill to flip through boxes of material and find an original November 1971 edition of Rolling Stone, the issue in which Fear and Loathing in Las Vegas was first serialized alongside Ralph Steadman’s iconic illustrations. I even found myself chuckling audibly while reading The Kentucky Derby is Decadent and Depraved in an old copy of Scanlon’s magazine, a much mythologized story the author considered his first work in the “gonzo” style.

(The Thompson Estate)

But what really floored me were four “Wall Posters” (22” x 15”) published in support of Hunter Thompson’s legendary 1970 campaign for Sheriff of Pitkin County, Colorado.

In the tradition of Thomas Paine’s Common Sense, these campaign broadsides mixed original artwork (including the campaign’s logo, a double-thumbed fist clutching a peyote button) with slogans like “Today’s pig is tomorrow’s bacon” and a selection of satirical articles that harnessed Thompson’s trademark mix of humor and venom to call out—by name—corruption and malfeasance among the local power elite.

Fifty years ago, in that epic campaign, Hunter Thompson called for cannabis legalization, aggressive environmental protection, and an end to abusive policing and corruption in government.

We should have listened.

The Battle of Aspen

Aspen in 1970 (Wikimedia Creative Commons)

As time went on, Hunter Thompson’s reputation as a larger-than-life celebrity party legend would occasionally overshadow his incredible talent as a writer. Like the time in Zaire when he smoked so much “black, grainy East African weed” that he neglected to actually cover the Ali-Forman fight. Or the time he almost accidentally drowned Bill Murray by duct taping him to a lawn chair and throwing him in a pool to see if he could make a Houdini-esque escape.

But perhaps his greatest and most outlandish drug-fueled prank was also his most serious and sober attempt to change the world for the better.

But perhaps his greatest and most outlandish drug-fueled prank was also his most serious and sober attempt to change the world for the better.

Back in 1967, Thompson used his first royalty check from Hell’s Angels to buy a small cabin in the wilderness outside Aspen, Colorado where he would live until he committed suicide there in 2005. Already a magnet for writers, artists, thinkers and misfits, Aspen offered a bucolic refuge from the chaos of his reporting life.

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Unfortunately, almost immediately construction began on a slag heap bordering his property. And the local authorities were real reactionaries. When an influx of hippies ascended upon Aspen to take jobs as cooks and ski instructors or simply to bum around town, the sheriff’s department began a campaign of heavy-handed repression against them, including allegations of false arrest and police brutality.

One afternoon the Sheriff’s department showed up at Aspen High School and searched every locker for weed based on an anonymous tip. Sheriff Whitmire himself, in a ten-gallon hat, with a pistol strapped to his hip, and a lit cigarette dangling from his lips, went through the girls’ purses, but found no contraband.

This open harassment of young people and “undesirables” would continue until a 29-year old lawyer named Joe Edwards filed the first civil rights case in Colorado history against the Aspen Police Department for discriminatory enforcement of ordinances that prohibited vagrancy, hitchhiking, trespassing, and blocking the sidewalk. Edwards’s eventual victory in the case made him an instant hero among the local counterculture.

It will be the general philosophy of the Sheriff’s office that no drug worth taking should be sold for money.

Then late one night Edwards answered the phone, and Hunter Thompson was on the other end, talking him into running for mayor. They would build upon his existing constituency of freaks by making a principled stand against out-of-control land development deals that were wrecking the environment, creating an affordable housing crisis, and transferring an inordinate amount of wealth and political power from the local community to a class of high-end grifters Thompson termed greed heads.

Ultimately, the Edwards for Mayor campaign fell six votes short, but it gave rise to an enduring Freak Power movement that pushed an even more outlandish candidate in 1970—Hunter S. Thompson for Sheriff of Pitkin County.

They even shot a campaign ad, featuring their candidate riding a motorcycle through the mountains over the following narration:

“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.”

“A Unique and Very Human Ambiance”

Hunter S Thompson Interview, 1970 (AP)

According to the excellent book Freak Power: Hunter S. Thompson’s Campaign for Sheriff, chief among the candidate’s campaign promises was ripping up the streets and sodding them, changing the name of Aspen to Fat City to “prevent greed heads and other human jackals from capitalizing on the name,” disarming the sheriff’s department, aggressively pursuing shady land developers and other environmental despoilers, and taking a public-health, harm-reduction-oriented approach to drug law enforcement so weird that it must be related in its own words.

“My first act as sheriff will be to install on the courthouse lawn a platform and a set of stocks in order to punish dishonest dope dealers in a proper public fashion… It will be the general philosophy of the Sheriff’s office that no drug worth taking should be sold for money. This will establish a unique and very human ambiance in the Aspen (or Fat City) drug culture, which is already so much a part of our local reality that only a fualangist lunatic would talk about trying to “eliminate it.”

So the only realistic approach is to make life in this town very ugly for all profiteers—in drugs and all other fields.”

In his public debate against Sheriff Whitmire, Hunter Thompson was asked if he thought cannabis possession should remain a felony for first time offenders. He replied “absolutely not,” and then added:

“The current laws were passed in a time of mass hysteria and total ignorance about marijuana. This single law has made felons out of an entire generation. The young people now look upon law enforcement as their bitter enemy. They consider cops to be narrow-minded racists who send out informants to spy on them and set them up for arrests, which can result in fantastic jail sentences…

Approximately 50 percent of the felony cases filed in Pitkin County in the last three years have been possession of marijuana. A hopeless waste.”

Super Freaks

Aspen in 1970 (Wikimedia Creative Commons)

The campaign may have started as an elaborate prank, but then a funny thing happened. Momentum began to build, and victory suddenly seemed possible. So much so that Hunter Thompson took out an ad in the Aspen Times to assure the electorate that he was indeed serious about being their Sheriff.

“This is a weird twist in my life, but despite the natural horror of seeing myself as the main pig, I think it has to be done. Or at least tried….”

Next, the Thompson for Sheriff campaign began publishing detailed policy statements and organizational charts to explain how their proposed reforms would make local law enforcement accessible and accountable to all citizens instead of just the affluent and influential.

Hunter Thompson went so far as to shave his head bald so that he could refer to Sheriff Whitmire as “my long haired opponent.” He also wrote an article for Rolling Stone titled “The Battle of Aspen” that brought national attention to the race.

The Washington Post ran with the headline “Hippies May Elect a Sheriff.” The next day the New York Times countered with “‘Freak Power’ Candidate May Be the Next Sheriff in Placid Aspen, Colorado.”

As Election Day neared, the entire town was in a frenzy. Opposition fliers were sent out depicting Hunter Thompson as a Nazi general. Voters who seemed likely to support the Freak Power ticket were harassed when trying to register, which lead to criminal charges against the County Clerk. The Colorado Bureau of Investigation warned Thompson of credible death threats against him.

Then things got really crazy, as Thompson described it in Kingdom of Fear:

“At one point [Sheriff Witmire] hired a phony outlaw biker from Denver—a veteran of two years of undercover work for the feds—who boomed into town one day on a junk chopper and first threatened to dynamite my house if I didn’t drop out of the race at once . . . then apologized for the threat—when it failed—and tried to hire on as my bodyguard . . . then spread rumors that people on my staff were in touch with Kathy Powers and a gang of Weathermen who planned to blow up all the bridges into town . . . then tried to sell us automatic weapons . . . then offered to stomp the shit out of anybody we aimed him at . . . then got himself busted, by accident, when the city cops found a completely illegal sawed-off 20-gauge pump action shotgun in his car—which they happened to tow away from a no-parking zone.”

The night before the election, Thompson and his core team paced the walls of his cabin outside town, which by necessity had been transformed into an armed encampment. The next day, the earliest returns showed Freak Power in the lead, but in the end they came up 400 votes short.

The Democratic and Republican parties in Aspen had conspired together to back a single candidate (the establishment-friendly incumbent) rather than risk losing a three-way race to someone neither party could control.

Celebrating Colorado’s First Recreational Cannabis Sale Five Years Later

And so Hunter Thompson lost the Battle of Aspen. But Freak Power would win the war.

In the next election, the entire Aspen City Council was voted out and replaced by Joe Edwards and other counterculture types. Then in 1976 Sheriff Whitmire was removed from his post amid accusations of misappropriating funds from the jail, and an ally of Hunter Thompson took over and enacted many of the Freak Power movement’s proposed reforms.

Aspen (alas, not “Fat City”), a town of just over 7,000 residents, now has seven cannabis dispensaries in its downtown core alone, and last year became the first city in history to have more cannabis sales than alcohol sales in a single year.

Something to ponder as I delve even deeper into the UCSC archive, just as the edibles begin to take hold.

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David Bienenstock
David Bienenstock
Veteran cannabis journalist David Bienenstock is the author of "How to Smoke Pot (Properly): A Highbrow Guide to Getting High" (2016 - Penguin/Random House), and the co-host and co-creator of the podcast "Great Moments in Weed History with Abdullah and Bean." Follow him on Twitter @pot_handbook.
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