Prior research has established the key impact of customers' Big Five personality traits (e.g., agreeableness/conscientiousness) on their brand engagement, suggesting that individuals exhibiting differing personality traits engage differently with brands. In parallel, extending influential customer engagement research, stakeholder engagement, which covers any stakeholder's (e.g., a customer's, supplier's, employee's, or competitor's) engagement in his/her role‐related interactions, activities, and relationships, is rapidly gaining momentum. However, despite existing acumen in both areas, little remains known regarding the effect of stakeholders' antisocial or maladaptive dark triad‐based personality traits, including machiavellianism, narcissism, and psychopathy, on the focal antisocial stakeholder's, and his/her interactee', role‐related engagement, as therefore explored in this paper. To address these issues, we develop a conceptual model and an associated set of propositions that outline the nature of a stakeholder's machiavellian, narcissistic, and psychopathic role‐related engagement and its effect on his/her interactee's engagement. We conclude by outlining pertinent theoretical and managerial implications that arise from our analyses.