This paper analyses flood management in the megacity of Jakarta. Complexities in flood management are influenced by the size of the megacity as well as political relationships among actors/stakeholders and different authorities of cities/districts in Jakarta. This chapter aims to discuss the changes in leadership styles of Jakarta. The analysis starts with the discussion of governor periods, tracking the different approaches to reduce flooding in Jakarta. This chapter evaluates the relationship between leadership and flood control activities. Finally, the chapter suggests a number of challenges and also recommendations related to leadership and risk governance.