Thomas Pynchon’s Vineland (1990) met with a lukewarm critical reception. Critics fond of the novelist’s postmodern theatrics rejected its political didacticism, whereas politically didactic critical opponents of postmodernism rejected its lingering individualism and antiauthoritarian thinking. Caught between this rock and hard place, the novel became a casualty of an ongoing battle within the Left between postmodernists and proponents of Old Left structure. Neither camp accurately assessed Vineland, however, because the anarchist politics on which it is structured have been poorly understood in the academy. Turning a historicist eye toward the novel’s portrayal of the sixties, we see that it dramatizes actual debates among the New Left between anarchist figures, such as Paul Goodman and Murray Bookchin, and emergent neo-Leninist factions such as the Weather Underground and Progressive Labor Party. Speaking to contemporary leftists, the novel concludes that decentralist and grassroots anarchist politics can mediate between the New Left’s entropy and the Old Left’s hierarchy.