In 1965, Hunter S. Thompson was years away from becoming the gonzo journalist of legend. Hell’s Angels, which would launch his career, was still a year off, and Fear and Loathing in Las Vegas even further. At the time, Thompson was just a twenty-eight-year-old whose lawlessness, search for work, and unrelenting poverty had driven him from one home after another, across much of the Americas.

That April, in a letter to a friend, Thompson expressed his affection for the Industrial Workers of the World (IWW), a revolutionary labor union whose itinerant members began organizing throughout the US in the early twentieth century. “I believe the IWW was probably the last human concept in American politics,” he wrote.

The line might come as a surprise, given that libertarians have long claimed Thompson as one of their own, citing his fondness for Ayn Rand, his membership in the National Rifle Association (NRA), and his well-documented enthusiasm for drugs. But Thompson’s avowed affection for the IWW wasn’t a stray remark — the politics that he extolled and participated in throughout his life had more in common with the radical left than the libertarian right. For Thompson, the enemy that had to be fought was a twin-headed hydra: oppressive, authoritarian government and soul-crushing, exploitative capitalism. Both were an affront to the individual freedoms he cherished.