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Political analysis following the 2016 elections has emphasized the salience of the division between urban and rural communities, Red and Blue America. In Wisconsin, this has meant understanding President Trump’s victory as driven by rural community’s resentment of a Madison and Milwaukee’s growing influence, wealth and power. Too often this narrative overlooks the politics of small cities in states like Wisconsin and the way that political resentment and exclusion can be generated within communities not just across them. I begin this paper by briefly examining the voting patterns of the 29 small cities in Wisconsin, finding that they present both internal political division and large swings between Democrats and Republicans in recent years. Next I explore the relationship between these partisan swings and this internal division through an in-depth case study of one city I call Wisconsin City. Drawing on ethnographic observation at more than 50 local events, interviews with 30 local leaders, activists and community members, and analysis of government records and local media, I find persistent patterns of inequality and exclusion in local political life. Moreover, I find that the areas where President Trump made his deepest gains in the community map relatively cleanly on to those that have long felt excluded locally. Finally, I explore two ‘spillover’ mechanisms that may explain how local grievances translate into partisan shifts in state and national politics.