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Richard Hofstadter’s 1964 naming and depiction of a “paranoid style” in American politics has been enormously influential in recent academic debates about “populism,” about Trump and his “MAGA” base, and about the pervasive evidence of conspiracy theorizing. In recent work I criticized his argument by situating it within a genre of liberal realism that, since The Federalist Papers, has depicted the resentful motives, demonizing rhetoric, irrational projection, and dangerous excess of what it has called “democratic,” then “mass,” and more recently “populist” politics. Against this genre, my paper would de-pathologize, politicize, and pluralize the trope of a paranoid style. I do so by arguing that features of what Thomas Pynchon called “creative paranoia” was indeed developed in richly varying ways by advocates of radically democratic theory and practice in the late 1950s and early 1960s, against the backdrop of the organizing paranoia of bipartisan, state-sponsored anti-communism. The premises and key tropes in theoretical texts by C. Wright Mills and Norman Mailer, the idioms invented by SNCC, SDS, and the FSM, as well as the literary form of Thomas Pynchon’s The Crying of Lot 49 all indicate a gestalt, mood, or style in which theorists and activists take up a hermeneutics of suspicion, both to disclose the grip and reach of racial, imperial, and corporate forms of modern power, and to interpret apparently discrete aspects of social and personal life as aspects or parts of a whole they called “the system.” At the same time theorists, activists, and literary artists in this moment linked this “paranoid” orientation, not to insularity, demonization, or violence, but to defending subordinated groups and recovering suppressed histories as features of an avowedly reparative politics. Attempting to prefigure a “beloved community” invested in the flourishing of every member, their conception and practice of “creative paranoia” served world-building projects committed to enlarging the circle of the we.