A revealing indicator of social fragmentation in metropolitan America is the proliferation of common interest developments (CIDs), communities defined by restrictive covenants, deed restrictions, community associations, and citizens groups that wield substantial political influence and power. In Phoenix, large-scale retirement communities represent a conspicuous form of CID, populated by Anglo, middle, and upper-middle class elderly migrants who display high levels of political organization and participation. We present a case study of heated conflict between retirees in Sun City West—who see themselves as separate from the larger metropolitan region—and surrounding communities in the Dysart School District. The conflict is fraught with age, social class, and cultural tensions and evolves around seniors wielding political muscle in defeating school funding measures, controlling the Dysart governing board, and seeking to de-annex themselves out of the district to avoid paying school taxes. We argue that political conflict between advantaged seniors and neighboring working class Latino communities is symptomatic of troubling divisions across urban social space in America, raising thorny questions about the nature and scale of community, political representation and power, and fostering the public good in the face of "secession of the successful" from the larger polity.