The Caribbean twin-island nation of Trinidad and Tobago entered a new era on 24 May 2010 by electing its first woman Prime Minister, the East Indian Kamla Persad-Bissessar. Using a Discourse-Historical Approach, this inquiry assays how Persad-Bissessar discursively constructed her claim to leadership in the election speeches of the 2010 We Will Rise Campaign. Both the processes of bonding with her electorate and demontage of her opponent Patrick Manning are attained by Persad-Bissessar with cautious linguistic choices, including the use of the ritual picong satire and strategic switching to Trinidadian English Creole. This paper explores complexities, struggles and inconsistencies of the Trinbagonian political scene by integrating a detailed assay of political discourse and the exploration of the social and political environment within which discourse as social practice is embedded.