"Convention, Context and Critical Discourse Analysis: 'Jim The Boatman' and The Early Fiction of Trinidad" re-evaluates the claim of colored authorship which has been attributed to a short story published anonymously, in the Trinidad Spectator in 1846. This re-evaluation is significant since 'Jim the Boatman" has been cited as part of a collection of writing in the emerging literary tradition of nonwhite authors of nineteenth century Trinidad. A critical discourse approach to identifying the writer, in this essay, proposes an alternative paradigm to traditional "plantation power structures" which have been used for identifying writers of anonymous texts, as they may override the cultural context of literary discourse formation in complex Anglophone Caribbean societies like Trinidad. Critical Discourse Analysis focuses specifically on the ways in which writers’ discursive behavior is the result of external sociopolitical pressures, and the strategies they use for textualizing their worldview, in their cultural contexts. This alternative paradigm is based on the researcher’s critical observation of the social context, discourse conventions, and language use in relation to anonymous texts.