But how, exactly, did Thompson achieve this status in a single decade? Looking back, we can identify four distinct developments that pushed Thompson into its unique niche in the media ecosystem.
Early in his career, Thompson admired the Kennedys, hated Nixon, and attended the 1964 GOP convention in San Francisco. Even so, he viewed American policy as a dead end. He wanted to follow Tom Wolfe’s example in The Streamline Kandy-Kolored Tangerine-Flake Baby (1965). An early version of New Journalism, this book profiled the Southern California hot rod scene as well as the spectacular growth of Las Vegas. Later, Wolfe portrayed the psychedelic scene around novelist Ken Kesey, whom Thompson had introduced to the Hell’s Angels. Before long, Thompson also carved out a place for himself as a student of exotic West Coast subcultures.
His outlook changed dramatically in 1968. By then, Thompson had befriended Hinckle, who was presiding Battlements magazine. Through his connection to the legendary San Francisco muckraker, Thompson learned that all hell would break loose at the 1968 Democratic National Convention. He asked Silberman to get press letters for him and booked a trip to Chicago. . His sources were correct: Thousands of protesters flooded streets and public parks, and police flailed provocateurs, peaceful protesters and observers. The clashes provided a dramatic backdrop to debates within the convention, particularly over the party’s position on the Vietnam War. Senator Edmund Muskie argued that the anti-war contingent wanted peace at all costs, the peace board was defeated and Hubert Humphrey received the party nomination. By the end of the convention, Humphrey and Muskie had earned Thompson’s enduring scorn.
The real story was on the streets, however, where Thompson backed down from the police brutality he witnessed. Fleeing from agitated cops on Michigan Avenue, he encountered two officers blocking his retreat to his hotel. As he later recalled, “I finally ran between the batons screaming, ‘I live here, damn it! I pay fifty dollars a day!’ Thompson told Silberman that the street battles made “all Berkeley protests feel like pastoral romps from another era.” In Chicago, protesters “got up and fought, and took unbelievable beatings. I witnessed at least ten beatings in Chicago that were worse than anything I’ve ever seen done by the Hell’s Angels. Because of this, Thompson added Democratic Mayor Richard Daley to his list of villains.