The theoretical discussion of how the decolonization of knowledge and being can become a tangible reality has gained notable prominence since the 1990s. The abstractness of theory, however, poses a challenge to the analysis of concrete paths of decolonization. Through the examination of the work of the Cuban installation and performance artist Tania Bruguera, this paper explores how art serves to bridge the gap between theory and praxis in relation to the goal of decolonization. Specifically, the paper addresses how the individual and collective manifestations of Bruguera’s artistic practice function as a decolonial site of political and social engagement in her home country of Cuba, as well as internationally. To this end, the paper traces the evolution of Bruguera’s performances that address power structures in post-revolutionary Cuba and the ways in which she negotiates the power dynamics of the international art world in order to ensure that her work is not co-opted by the Western colonial framework that she seeks to challenge. In doing so, my analysis of Bruguera’s work through the perspective of coloniality and decoloniality expands the critical conversation on how socially and political artistic practices can integrate decolonial theory into daily life. Furthermore, I provide insight into the evolution of a career that has continuously developed mechanisms to mitigate the individualization of the artist in order to demonstrate how Bruguera’s collective approach to art making constitutes her greatest contribution to the terrain of decoloniality.