This article was prepared for the Critical Media Literacy Conference in Savannah, Georgia in 2016. The central argument of the article is that Donald Trump's candidacy emerges from a new strategy: branding. The author explores the decade prior to Trump's rise and his political forebears, as well as consults critical marketing and television studies to explain how Trump has been able to secure the nomination of the Republican Party despite having little institutional support. Instead, Trump's rise, like that of Sarah Palin and others can be attributed to the use of social media to brand their personalities as political outsiders to establishment politics.