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Scholars have begun calling for broader conceptualisations of moral disengagement processes that reflect the interaction of dispositional and situational antecedents to a predilection to morally disengage. The authors argue that collective leadership may be one such contingent antecedent. While researching leaders from the Gilded Age of American business history, the authors encountered a compelling historical case that facilitates theory elaboration within these intersecting domains. Interpreting evidence from the embittered leader dyad of Andrew Carnegie and Henry Clay Frick, the authors show how leader egoism can permeate moral identity to promote symbolic moral self-regard and moral licensing, which augment a propensity to morally disengage. The authors use insights developed from our analysis to illustrate a process conceptualisation that reflects a dispositional and situational interaction as a precursor to moral disengagement and explains how collective leadership can function as a moral disengagement trigger/tool to reduce cognitive dissonance and support the cognitive, behavioural, and rhetorical processes utilised to justify unethical behaviour.