The Caribbean twin-island nation of Trinidad and Tobago entered a new era on 24 May 2010 by electing its first woman Prime Minister, Kamla Persad-Bissessar. Breaking out of the country’s rigid bipolar political mold, the East Indian Persad-Bissessar won a landslide victory as the leader of the People’s Partnership, a new coalition party that comprised both East Indian and African political forces and movements. Adopting a Discourse-Historical Approach, this study sets to analyze 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 achieved by Persad-Bissessar with careful linguistic choices, encompassing the use of the ritual picong satire and strategic switching to Trinidadian English Creole. This article investigates complexities, struggles and contradictions of the Trinbagonian political scene by integrating a detailed analysis of political discourse and the investigation of the social and political environment within which discourse as social practice is embedded.