As the Cuban state continues–– in its own language–– to “update” its economic model to recognize private property and the role of the market while maintaining socialist principles, contemporary Cuban visual artists find themselves balancing neoliberal expectations of entrepreneurial agency within an ideological heritage that emphasizes the collective and demands social commitment. In light of seemingly contradictory legislation recently enacted on the island, this project asks: What concepts of property are exposed and reworked by Cuba’s contemporary avant-garde? By focusing on the Cuban artworld’s active negotiation of the relationship between property and the figure of the artist in a period of fundamental political and economic realignment, my proposed dissertation research follows artists as they reflect and refract the particular dilemmas of postsocialist, postcolonial societies, as well as the ever-present promise and disappointment of art’s attempts to prefigure and materialize a better future. Through twelve months of ethnographic and archival research examining artists’ self-presentation, material production, and exhibition strategies, I will investigate Havana’s artworld as it responds to, and potentially shapes, domestic political-economic reforms. Additionally, in paying particular attention to the Havana Biennial, my project expands social science and humanities inquiry into global artworlds, locating contemporary Cuban art at the intersections of (post)socialism, neoliberal capitalism, and the postcolonial Global South. I advance a critical anthropology of cultural production by placing an ethnographic reading of artworks and artists’ public persona within a methodological approach that investigates how both are generated and constrained by broader political economies. I attend to art and artists to understand ongoing social, economic, and political transformations in Cuba. Similarly, I look at property regimes, models of personhood, state power, and social change to understand an international artworld coming to terms with a globalized postsocialist, postcolonial present.