This paper explores the mutual relationship between large group regression and leadership with the characteristic of the syndrome of malignant narcissism. Regressed large groups intuitively search for such leadership and personalities with these characteristics are prone to aspire to the correspondent role. The underlying dynamics of groups and leaders are complementary and determine a mutually reinforcing psychopathology. This paper will explore these dynamics, their social consequences, and discuss potential preventive and therapeutic interventions that protect society from this psychosocial psychopathology.