Charismatic leadership contributed to the shaping of politics in Panama and Puerto Rico, in particular through the careers of Arnulfo Arias and Luis Muñoz Marín, respectively. Based on an examination of their trajectories, this paper seeks to further illuminate the relationship between charismatic leadership and democracy. As suggested by Weber, as argued by the literature on Latin American populism and personalism, and as shown by Arias's political legacy, the ‘charismatic mission’ can promote plebiscitary democracy. But can charismatic authority also foster representative democracy? Muñoz Marín's career provides interesting insights in this regard.