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The following is a case study of the Enron Corporation under the leadership of Jeffrey Skilling. I argue that charisma was integral to Skilling’s ascension and to the decoupling of Enron from the patrimonial ethos that characterizes financial elites. I argue that charisma was integral to potentiating the political, cultural, and structural embeddedness that led to malfeasance in the case of Enron. This embeddedness was shaped by inequality regimes and the hegemonic masculinity characteristic of high finance. Contra Joosse and Willey 2020, I argue that culture functions as a substrate in the production of charismatic leadership. As leaders use their charismatic relationship to develop a mythos and cult of personality, they will reproduce inequality as it is the low hanging fruit of garnering legitimacy. I argue that this becomes embedded in the language of the organization and is uptaken differentially across the organizational structure, as those who are most culturally fit will be awarded the most trust within the organization to enact the conspiracy and engage in criminality. Pockets of hegemonic masculinity and corruption will emerge. This hypothesis is tested empirically using a qualitative, iterative, and abductive analysis of the Enron Email Corpus (81,365 emails sent from 4,022 professionals). The findings suggest that this hypothesis and theoretical framework need further refining, as speech acts connected to criminal activity show a reduction of cultural content and an eliding of agency. Conspiratorial language is marked by qualities of professionalism and passivity. Informal communication reveals the kind of cultural masculinity expected among corrupt network participants.