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From the Tea Party to Donald Trump, Bernie Sanders to Alexandria Ocasio-Cortez and the rest of “the Squad,” American politics is being reshaped by party insurgents. Yet, despite their significance, political scientists have not developed any systematic understanding of the role that these catalytic agents play in processes of party change or their impact on the quality of representation and democratic governance. This paper addresses this gap in two ways. First, this paper theorizes insurgents as entrepreneurial agents operating at the intersection of movement and party politics. I argue that, despite the fact that most insurgents fail to win their party’s nomination or the general election, they still exert lasting influence on American politics by forging durable links between parties and movements. Second, while insurgents may lay the groundwork for injecting new ideas, policies, and coalitions into the mainstream, they do so by destabilizing politics, shattering established norms, and undermining public trust in representative institutions. Thus, insurgents have the paradoxical potential to revitalize democracy while also facilitating democratic backsliding.