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Most of what goes on in political discourse tends to accommodate to conscious psychology and rational thinking; nonetheless, there remains a perplexing, powerful and much less visible, primarily unconscious piece that can help address the chaos that threatens democracy's rather fragile nature. The limits of rational thinking become apparent when we consider the forceful powers of phantasies underlying human destructiveness. Consequently, including a psychoanalytic lens is essential to appreciate how and why a rational approach, while necessary, remains insufficient to grapple with the non-rational, unconscious and highly emotionally charged forces in American politics as well as in democratic-leaning movements worldwide. This paper seeks to deepen understanding through addressing such components as the long-standing nature of American populism and its relationship to both democracy and authoritarianism; the conditions leading to large-group regression as well as the unique fit between malignant leadership and perverted containment within regressed groups; the psychic mechanisms, including delusional and other psychotic processes, that turn a regressed large group into a personality cult; and finally, the unique contributions psychoanalysis can make in managing such regressive, malevolent dynamics to help chart a realistically hopeful path forward.