Seen through the lens of Republican candidate Donald Trump’s reality TV program ‘The Apprentice,’ his promise to American voters that they’ll tire of "winning" under his regime takes on a darker meaning. This article identifies ‘the loser’ as a potent new political symbol emblematic of ‘contestants’ who in the face of mathematical loss become ‘bigger’ losers if they fail to assert their right to a non-meritorious victory. The fact of one’s loss is not as important as one’s reaction to it. To lose is possible, but to be a ‘loser’ is the ultimate humiliation that justifies taking extreme, even immoral measures. Contestants who are willing to ‘do anything’ to win are rewarded more generously often than those who, in reality, are the rightful winners. Such a perspective rationalizes a politics of exaggerations, lies and defamation. Extending Couldry and Littler’s discourse of passion, we identify the mechanism that enables and compels some voters to embrace Trump’s divisive politics of ‘otherism’ as astute ‘game playing.’ In Trump’s world, to win means many more must lose. Just as in the reality TV world, however, Trump alone holds the power to annoint winners and exile losers, meaning there is no guarantee of success for anyone but him.