This critical sociolinguistic paper adopts a materialist view of how multiple languages and identities are negotiated in an effort to re-examine multilingualism and why people invest in certain sociolinguistic practices. The focus is on the social and linguistic resources and performances of Portuguese-Canadian youth in student cultural associations or clubs in Toronto. The sociolinguistic work carried out in these Portuguese clubs provides a rich context in which to explore diverse linguistic repertoires and trans-local identities which are the hallmark of a postmodern, globalised world. These student associations are flexible transnational spaces where young people should be free to construct their multiple sociolinguistic identities as they see fit. They should be able to assert their creative agency without the constraints of traditional ethnolinguistic gate-keepers like Portuguese teachers, parents or community leaders who can impose homogenised or "legitimate" ways of speaking and being Portuguese. Yet, this hypothetical freedom and flexibility are not easily achieved and they often come at a cost. At issue are questions surrounding authenticity, legitimacy, dominant linguistic and nationalist ideologies, and access to material and symbolic capital that structure the Portuguese-Canadian community as a market and position some people as "heroes" of the Portuguese cause, and others more like "zeros".