The dysfunctional workplace, ruled by the controlling, manipulative, and abusive boss, is a staple of our popular culture as well as the object of sustained investigation by scholars in a variety of disciplines. The misery occasioned by bullying bosses is all over the internet, and observers have long documented the cost of the same to companies, organizations, and economies. Yet the workplace continues to serve as a site for the expression of aggression and casual brutality despite our ever-more-refined characterologies and interventional strategies.

In this paper, I examine this recalcitrant issue, focusing on a fundamental ambivalence about the leader’s character as sketched by psychologists, psychoanalysts, and other students of management and leadership. In this literature, the leader’s charisma, creativity, and even authoritarianism are deemed essential but also of a piece with the callousness, paranoia, and destructiveness that bring organizations to ruin. This ambivalence finds support in the wider culture, which celebrates a risk-taking grandiosity in leaders that is at odds with calls for supporting employees’ autonomy and recognizing their competencies.

I then examine the organizational writings of the psychoanalyst Otto Kernberg, who chronicled the “sadism, corruption, and envy,” all forms of “rationalized aggression,” that in his view coursed through social and organizational life. Kernberg’s work has proven foundational to studies of the workplace and its deformities. “The more cautious and refined manifestations of human aggressiveness” that Freud, in Civilization and Its Discontents, cast as beyond the law’s reach formed the stuff and substance of Kernberg’s dystopian vision. His gallery of pathologically narcissistic types and his catalogue of the ways that we as humans make one another miserable resonates with the well-known dictum that for moderns “hell is other people.” I conclude by assessing the foundational nature of Kernberg’s contributions to studies of our undercivilized selves in the modern workplace.