In this multisite case study, we examine the personal capacities of six high school principals who have developed the leadership capacities of other leaders in their respective schools. Participants were purposefully selected by two teams of researchers in two states of the United States, one on the east coast and one on the west coast, who engaged their professional networks of current and former educational leaders to obtain recommendations of high school principals known for developing the leadership capacities of formal and informal leaders in their schools. The findings indicate that the principals possessed a strong commitment to developing leadership capacity, that they understood leadership development as a process, and that they tolerated risk. This study adds to the rapidly growing corpus of literature focused on distributed leadership; it does so by illustrating the complexities of developing leadership capacity in attempts to increase organizational leadership capacity, and by highlighting the relevant characteristics of principals who have intentionally sought to do so.