The essay examines the role of The Ontario Society for Services to the Indo-Caribbean Community [OSSICC], a historic organization that sought to assert the dignity and re-discover the identity of Indo-Caribbean persons as a fragment of the Caribbean diaspora in Toronto, Canada. While it points to the achievement in representing the interests of its members for symbolic cultural recognition, it underscored the limitations in the political arena for empowerment, power sharing, and equality in employment opportunities and for an equitable share of the resources of the state. Further, it describes how the ethnic conflict in the homeland persisted in the new site of the diaspora, about lost opportunities for healing, and about inter-generational discontinuities in the reconstruction of the Caribbean self. On a larger scale, the article is about membership and citizenship in the new homeland of the diaspora, its seductions and betrayals in the new frontier of Canadian multiculturalism.