Leaders in the Crossroads considers two intriguing issues: an exploration of the characteristics that determine success and failure in the academy's top post and the impact of that post on a college. An evaluation of the responsibilities and challenges presidents face, and how they speak and lead, is a fair way to explore realities about college presidents and their successes and failures. How do presidential leadership, rhetoric, and action connect to the fundamental beliefs and values at the foundation of the university? Are presidents able to make a difference, and if so, how do they contribute to the legacy of the university? College presidents are noteworthy leaders in and outside the gates. Deliberations about the success and failure of the presidency, and its obligation to the foundations of the academy generate more questions than answers. However, this inquiry is crucial because it sheds light on the college presidency and on its relationship to the future of the university.