Most contemporary explanations of congressional leadership postulate a version of contextual theory that typically places greatest emphasis on the strength of party and downplays the personal skills of individual leaders. By analyzing the leadership of just three recent individuals—Gingrich, Hastert, and Lott—this essay demonstrates the extent to which these leaders' different styles, skills, and characteristics interacted with changing political contexts and strategic environments to impact political and policy outcomes. Context matters, but so does leadership skill. Most graphically, Gingrich—a rare transforming leader in Burns' typology—demonstrates the importance of the right person and the right conditions being in place at the same time and the ability of an individual imaginative leader to intervene exogenously to have a significant effect on policy outcomes. Yet the essay also demonstrates that even where leaders adopt more conventional transactional styles, as Hastert and Lott did, the skill and success with which they juggle political pressures emanating from different, often conflicting, contexts—skills in context—also matters.