In a number of African countries, civil conflicts have ended with awkward transitions from military rule to civilian leadership. Regular multiparty elections have become the norm in most of these countries, leaving former guerrilla leaders, military officers, and other assorted “big men” with little choice but to put away their guns and begin second careers as politicians, asking citizens for votes. This collection of essays assesses how this phenomenon has shaped African democracy. A probing essay discusses the career of Rwandan President Paul Kagame and makes clear that the strategic skills he developed as a guerrilla commander have helped him entrench himself as a strongman ruler. Other informative chapters profile less well-known figures, such as João Bernardo “Nino” Vieira of Guinea-Bissau, Afonso Dhlakama of Mozambique, and Riek Machar of South Sudan. The book’s main takeaway is that the role of such men in postconflict democracies remains generally negative, in part because once in power, they tend to adopt approaches anchored in their pasts.