It seems as of late the most acclaimed advertising campaigns have found a formula to commodify the politically correct through what has come to be described as “woke advertising”. This winning strategy has won public appeal for connecting with an ever-evolving audience that is young, diverse and liberal. Specifically, newcomer agency, Anomaly, has publicly proclaimed themselves as the “change-agent” in the space of advertising, capitalizing on the culture wars by positioning themselves as the leading advertising experts in challenging societal stereotypes and biases. This is a case study that explores one of Anomaly’s 2016 campaigns for Johnnie Walker, “Keep Walking America”, as they attempt to engage in cultural politics with the Latinx community during a period of heightened political tension for immigrant populations. Through a Social Semiotics analysis and postcolonial criticism, the focus of this thesis is to explore how Johnnie Walker leveraged woke capital and consequently attempted to represent the lived experiences of marginalized groups whose stories are generally silenced.