This essay offers an initial account of the Occupy Central movements of 2011 and 2014, focusing on the dynamic practices and processes of the two occupations through a comparative perspective. It provides a description of the scenes, demands and relationships of ordinary occupiers at the protest zones and considers the implications of the “leaderless” logic in relation to the organization of popular power. Contrary to the romanticizing notion of a leaderless movement and the celebration of Occupy Central as “a spontaneous one without leaders and without the need of leaders”, I propose that it is necessary to pay attention to the tensions and confrontations taking place within the movements. Although the first Occupy Central “set seeds of possibility, gave a sense of new modes of organizing, of direct democratic expression”, its leadership and organizational problems resurfaced in the second occupy protest. The struggle over the freedom to nominate and elect a leader–as manifested in the second occupy movement–has been paradoxically dismantled by its leaderless propensity. The historical conditions that have facilitated the condition for a “leaderless” and “spontaneous” movement and the consequences engendered by these tendencies deserve a critical analysis. The case of Hong Kong, with all its ambivalence about hierarchy and representation, raises deep questions about the notion of leaderlessness and the privileging of tactics over strategy in the context of the global waves of occupy movements.