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.

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.

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.

Fear and Loathing at the Start

Thompson’s upbringing was a story of class mobility — in the wrong direction. Born in Louisville, Kentucky in 1937 to an insurance agent and a librarian, Thompson was in high school when his father passed away, knocking his already struggling family further down the social hierarchy.

That must have been brutal enough in Louisville, which at the time was sharply split between Southern gentry and the working class. But it was soon punctuated by a run-in with the law. Arrested with two friends for a mugging he didn’t commit, Thompson was given the option of jail or the military — while his friends, the sons of prominent lawyers, got off immediately. “We all dismissed that,” a childhood friend of Thompson’s recalls in the oral biography Gonzo, “but it stayed with Hunter for a long time.” Thompson chose the Air Force over imprisonment, but also over remaining in Louisville.

Some of the earliest glimpses of Thompson’s politics can be seen in his letters (the first volume of which was published in 1997 as The Proud Highway). In epistles to a childhood friend, Thompson praised not only the IWW but Karl Marx (“I find it’s not necessary for me to read Marx because I already agree with him”), Fidel Castro (“a man with enough balls to try and whip things around to a decent position”), and libertarian socialists (“I am at home with anarchists anywhere”).

Other early letters saw Thompson expressing his appreciation for arch-libertarian Ayn Rand and gushing over The Fountainhead (while admitting to having never read Atlas Shrugged). Thompson said he felt a kinship with Howard Roark, the hyper-individualist hero of The Fountainhead, writing to a friend, “Although I don’t feel that it’s at all necessary to tell you how I feel about the principle of individuality, I know that I’m going to have to spend the rest of my life expressing it.”

But Thompson was also critical of capitalism for limiting human flourishing and individual freedom, especially his own. A few years later, he would invoke the IWW and write, in reference to his bosses, landlords, and creditors: “I feel like I’ve been leaned on for a long time by people who don’t even have to know my name and should probably have their fucking heads blown off on general principle. I have in recent months come to have a certain feeling for Joe Hill and that Wobbly crowd, who, if nothing else, had the right idea.”

Thompson’s relationship with the NRA was similarly complex. According to correspondence collected in The Proud Highway and his second volume of letters, Fear and Loathing in America, Thompson joined the NRA in 1962, but let his standing lapse repeatedly, stressed that his membership was “in no way indicative of any political views,” and considered leaving six years later because of the organization’s “stupid grumbling about maintaining an armed militia.” Thompson simply loved guns — that was the long and the short of it. As he admitted to his agent in a 1968 letter: “There may or may not be a valid argument against nationwide gun registration, or even against guns. I’m not sure and I don’t really care.”

The political views that were central to Thompson were the ones he advanced through his writing and activism, which were deeply entwined. In his forthcoming book Freak Kingdom, biographer Timothy Denevi describes how Thompson abandoned his dream of becoming a novelist in the early 1960s to focus on journalism — partially to pay the bills, but also to try to change the course of US politics, which he feared were taking an apocalyptic turn following the assassination of John F. Kennedy. Denevi’s book covers Thompson’s life from 1963 to 1974, a period that saw the publication of Thompson’s most important works — including Hell’s Angels, Fear and Loathing in Las Vegas, and Fear and Loathing on the Campaign Trail ’72 — as well as his most intense political organizing: for Jay Edwards’s campaign for mayor of Aspen, Colorado in 1969, for his own bid for sheriff of Pitkin County, Colorado in 1970, and for George McGovern’s run for president in 1972.

Even before committing himself to political journalism, Thompson’s fiction delved into issues of class and exploitation. The Rum Diary, his second completed novel (the first remains unpublished), tells the story of Paul Kemp, a newspaper reporter who moves from New York to San Juan in search of paradise. After his paper goes under, Kemp finds a lucrative lifeline in writing ad copy for the luxury resorts cropping up around Puerto Rico. But rather than feel content with “being paid twenty-five dollars a day to ruin the only place I’d seen in ten years where I’d felt a sense of peace,” Kemp decides to return to New York.

A similar, though much harsher, indictment of capitalism can be found in Thompson’s first published novel, Fear and Loathing in Las Vegas. There, he describes Vegas as not only the purest distillation of the American Dream, but also, as Denevi writes in Freak Kingdom, “a place where the very few take everything they can from the people who keep coming back — all the while providing endlessly diabolical entertainment so as to numb and distract from the repeated pain of loss.”

Thompson initially avoided injecting himself and his values into his journalism, yet traces of anticapitalism still appeared. Much of his early reporting — published in the 1979 essay collection The Great Shark Hunt — was produced on a tour through South America in 1962 and 1963, and the subjects are telling: smuggling, US imperialism, indigenous rights. From a certain angle, even Hell’s Angels can be read as a critique of capitalism: Thompson describes the bikers’ fascism as a noxious byproduct of early deindustrialization and capitalist alienation.

If Thompson used his writing to excoriate the United States for its depravities — capitalism chief among them — then he used his activism to promote radical alternatives. In 1969, he was the one who convinced local attorney Jay Edwards to run for mayor of Aspen and who helped formulate policy proposals that prioritized the needs of residents and the environment over those of developers. Thompson’s bid for sheriff the following year — sometimes wrongly characterized as a joke — was based around a similar platform, like fighting capitalist development and pollution, while also upping the ante with ideas for disarming police and decriminalizing drugs.

When the 1972 election came around, Thompson donned both his journalist hat and his advocate hat. The result was his greatest nonfiction work, Fear and Loathing on the Campaign Trail ’72. Reporting from the campaign trail for Rolling Stone, Thompson savaged incumbent Richard Nixon and most of the Democratic primary contenders (party favorite Ed Muskie, machine boss Hubert Humphrey, and segregationist George Wallace), while advocating for George McGovern. Although McGovern went down in defeat, his policy proposals were quite radical: in addition to ending the Vietnam War, he proposed implementing a guaranteed minimum income.