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Drawing on the contributions of psychoanalysts influenced by Bion as well as on sociopolitical historians, the author examines Trumpism and its destructive leadership through the lens of such concepts as alpha functioning, beta elements, second skin and beta-screen, projection, and containment. The article demonstrates that a vindictive, narcissistic, and toxic masculine leader such as ex-President Trump serves to “pervert” the containing function of healthy leadership to increase authoritarian rule. The author shows that when there is a fit between the group’s unconscious phantasies and malevolent, narcissistic leadership, the stage is set for the development of a malignant cult of personality. The cult of Trumpism fosters and exploits paranoia and allegiance to an all-powerful, charismatic figure, contributing to a social milieu at risk for the erosion of democratic principles and the rise of fascism. In contrast, to illustrate healthy containment that neutralizes potentially destructive psychotic anxieties and fantasies, the author closes with sensitive and inspirational leadership oratory from Abraham Lincoln and Robert F. Kennedy.