The term “anti-establishment” has witnessed a revealing rise in recent American political discourse. Combining textual analysis of news coverage and speeches with in-depth interviews with dozens of consultants involved in the encoding of mediated political communication, this research analyzes and critiques its deployment and significance in Republican campaign messaging. Mapping the contours of this rhetorical strategy, a typology of four dimensions of tension emerges: insurrection versus order; populism versus insider power; real America versus elitism; and purity versus compromise. As an exercise in critical political communication, the argument concludes that “anti-establishment” rhetoric seeks to stoke and co-opt resentment while effacing powerful, privileged economic interests.