The Caribbean and Taiwan appear to be more than oceans apart. Although there are ostensible similarities between the Caribbean and Taiwan, such as their complex colonial histories and insular spaces, these two names usually are not mentioned in the same breath in Western academe, and Caribbean studies scholars are unlikely to cross paths with those who engage in Taiwan studies. Furthermore, for the average reader in either location, they conjure up only vague ideas and stereotypical images of each other mediated by the West. In light of the reception of Caribbean literature in Taiwan, this essay seeks to explore the reasons for and ramiﬁcations of such a disconnect between the Caribbean and Taiwan, with an examination of the status of imported knowledge within the Taiwanese context and Taiwan’s positioning vis-à-vis the Caribbean in the global system of knowledge production. It argues that what may seem a far-fetched comparison between the two sheds light on Taiwan’s potential relations with the Caribbean as well as its relations with the other foreign inﬂuences that Taiwan has had to grapple with throughout history in the continual (re)shaping of its collective identity. If Taiwan has had to battle and outwit globalizing tendencies that relegate it to political, cultural, and epistemological insigniﬁcance (Shih 2003), then I propose that forging unlikely relations and alliances with other marginalized or dominated groups, countries, and cultures can be an alternative to making Taiwan relevant, even signiﬁcant, to the rest of the world.