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Friendship is one of the most important aspects of private life. It provides the social and relational support for integrity, growth, and intimacy. At the same time friendship can be vital to the life of a public leader. Friends anchor integrity and offer trust, honesty, and loyalty based on past experience. Using the classical ideal of friendship developed by Aristotle and Cicero, this article argues that friendship consists of a mutual and exclusive relationship built on a unique affiliation between two people that can transcend the bounds of office and obligation. The central thesis is that the obligations of leadership place demands on leaders for detachment, judgment, and political calculation that are in tension with the obligations of friendship. The article explores two major strains that arise between friends and leaders-the temptation to use friends and the temptation to give friends special treatment. The article concludes with a preliminary suggestion that friendship with leaders at work is very difficult, but it can be sustained with a strong basis prior to working together, a clear understanding of roles, and the ability to keep honesty and affection alive in the relationship.