Whiteness, understood in psychoanalytic terms as a complex emerging in relation to an invidious object, catalyzes character disorder and mass violence. Drawing on historical analyses of the early American colonial period and a 2014 mass shooting in Isla Vista, California, I articulate a theory of the workings of Whiteness, with an eye toward the interrelationship of psychodynamics and sociocultural, structural, and ideological forces. I conclude with a consideration of how and why psychoanalysis has failed to fully contend with Whiteness because of the discipline’s own investment in Whiteness and White aggression.