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Over the past two decades political scientists have become increasingly concerned with asymmetrical polarization: that is, the fact that Republicans have shifted significantly further to the right than Democrats have to the left. Yet few have offered a systematic explanation for why systemwide polarizing pressures have affected the two parties so differently. This paper addresses this gap by developing a novel theory of parties and party change centered around the contentious relations between party officeholders in government and their allied groups and mass publics in society. Foundational to parties as mediating institutions, these contentious relations condition the party-building and alliance-making strategies of party leaders, political entrepreneurs, and other party stakeholders. We argue that Democrats’ and Republicans’ varying patterns of party-building and alliance-making activity since the early post-WWII period put the two parties on distinct and increasingly divergent developmental trajectories. Democrats’ sustained electoral success and broad support from labor, civil rights, feminist, environmental, and (later) LGBTQ+ movements disincentivized forward-looking investments in their party organization. By contrast, Republicans’ persistent minority status in Congress and lack of powerful movement allies before the late 1970s incentivized robust patterns of party building. Consequently, Democrats entered the polarized era with a diverse coalition of allies but a hollow organizational structure, while Republicans married a belated alliance to media-mobilized conservative groups with a relatively strong organization for them to penetrate and take over. These distinct developmental paths have produced two sharply contrasting party orders in the present: one animated by an inclusive ideological commitment to a diverse coalition of interest group advocates; the other, by a populist distrust of government and a coalition united around deconstructing the administrative state.