Donald Trump's rhetoric of winners and losers has prompted dangerous division in the United States. It is well understood that Trump's divisive discourse appealed to white, blue-collar Americans who had become disillusioned with the political establishment. This study explores how Trump persuaded this audience by transitioning business communication principles, highlighted by his signature 'winners and losers' theme, into politics. Trump's use of the reality television show, The Apprentice, as a branding platform had the rhetorical effect that catapulted Trump's unique 'winning' brand back into the public's consciousness. While the principles of business rhetoric Trump used in The Apprentice were clearly transitioned to Twitter during Trump's 2016 presidential campaign, his tweets were unique in how they foregrounded the 'losers' he faced during the campaign. To illuminate Trump's branding strategy as both TV personality and political candidate, this analysis of Trump draws on Kenneth Burke's concept of consubstantiation and contemporary theories of business rhetoric, namely the idea of narrative-processing and its influence on consumers' connection with a brand. Because Trump constructs his brand with language that aims at restructuring America's social hierarchy, this study also uses critical discourse analysis (CDA) to understand the implications of power for both his audience and his opponents. This study concludes that while Trump's winning brand identity contributed to him winning the presidency, it also promotes male dominance and exacerbates political division in the United States.