In 1970 Thompson ran for Sheriff of Pitkin County, Colorado on the Freak Power ticket. He announced that he would spearhead several reforms:
rename Aspen to "Fat City, Colorado"
tear up the downtown streets and replace them with bike paths
decriminalize drug possession
decriminalize the sale of drugs (but only at cost)
reintroduce the stocks for drug dealers working at profit
As the Republican sheriff he was running against sported a crew cut, Thompson shaved his head bald and referred to the other candidate as his my long-haired opponent. Even so, he lost the election.