This paper examines the complexity and multidimensional features of leadership and provides understanding of leadership in ASEAN integration. It highlights the significant roles of leadership in the integrating Southeast Asia and contradicts its common belief of invisible leadership. It highlights the role and the importance of Indonesia in the development of ASEAN as a main factor that can determine ASEAN's survival and success. Moreover, it insists that ASEAN is literally subject to structural powers, derived from material and resource capacity, in which leadership is highly attached to a leader's charisma. Finally, the paper proposes that the benevolent roles of Indonesia with strong emphasis on soft power are a key element of success.