Some are born great, some achieve greatness, and some have greatness thrust upon them."-W. Shakespeare, Twelfth Night, Act II Scene v. Leadership has various permutations, including transformational, distributed and integrated authority, to mention just a few. Although these forms of influence may be viewed positively, not all leadership is positive. This article addresses the "dark" or dysfunctional side of leadership. Dysfunctional leadership is inherent in all forms of leadership, and exists independently of leadership style. Dysfunctional leadership comprises an amalgam of contextual conditions, personality traits and specific situational circumstances. Consequently, "dark" or dysfunctional leadership may be ameliorated or exacerbated by the type of task, personality of the leader, or even a mismatch of leadership style to specific contexts. Philosophies of leadership or issues of power may also derail positive leadership. Additionally, mis-educative strategies, such as binary thinking, template approaches and "decision driven data-making," as opposed to data-driven decision-making, reduce leadership to a dysfunctional enterprise. However, even dysfunctional leadership may not be entirely negative, as some experiences may be educative, although they may not be positive.