Directly elected mayors are on the rise internationally. Enthusiasts for this form of local political leadership claim that it can provide visible, strategic, accountable leadership for cities. Opponents argue that the model concentrates too much power in the hands of one individual, and that it can result in local government decision-making being skewed to serve powerful economic interests. This chapter offers a contribution to this debate. An opening section outlines a way of conceptualising the political space available to place-based leaders. It is then suggested that, in any given locality, there are likely to be different realms of leadership, with players from inside and outside the state making a significant contribution to urban policy making. Three examples of bold and progressive mayoral leadership are then presented in the form of three short cameos: Greater London, UK (in the period 2000-08), Portland, Oregon, USA; and Freiburg, Germany. The comparative discussion of mayoral leadership that follows is structured around three themes: the role of directly elected mayors in expanding place-based power; connecting the realms of place-based leadership and bringing progressive values back into city politics.