This essay argues that in the early- to mid-Trump era – starting with his active campaign for the US Presidency in 2015 and through his subsequent administration pre-Covid through February 2020 – working-class bodies were used in advertising to both contest and enact prominent values and ideological tensions that became prominent during Trump’s reign. Advertising used class-based representations in several ways: to critique Trump and his policies; to depict working-class hardships under Trump; and, conversely, to celebrate white working class masculinity, authoritarianism, and classed masquerades. Each of these themes highlights a particular tension indicative of the Trump era. Often contradictory, such representations exemplify stereotypes about the working-class and serve to solidify enduring and often stifling lessons about class in society.