This essay reflects on the contribution made by  Timed Out: Art and the Transnational Caribbean  (2011) to alternative futures for the Caribbean-focused study of art and its histories. Wainwright emphasizes the need for better attention to the complex “geopolitics of time” that is central to the formation of Caribbean creative experience, and outlines the discursive field, the art market, and the policy and funding landscape through which Caribbean and diaspora artists move. In response to the discussion of  Timed Out , in this issue of  Small Axe , Wainwright explains the continuing need to explode the existing dominant art canons (while highlighting the problematic assimilation of counterdiscursive and plural positions) and proposes various pathways by which the Caribbean's role in changing powerful modes and priorities of art historical scholarship may be extended fruitfully to the wider humanities.