In August 2001, the state-run Control Board for the Chester-Upland School District awarded control of nine of their 10 schools to Edison Schools, with little opposition. In contrast, nearby Philadelphia fought state efforts to privatize schools. Finally, on July 31, 2002, the joint state-city Philadelphia School Reform Commission partially privatized 45 (17 percent) of the city's 264 public schools, while partly reconstituting 41 others. Published sources, fieldwork, and semi-structured interviews with 26 policy makers and educators are used to explain the different approaches to privatization. The small size and related low community involvement of Chester, Pennsylvania, enabled the state to conduct more thoroughgoing policy change with less opposition. Further, Philadelphia schools had made some progress in the 1990s, while dire conditions in Chester encouraged more extreme reform. Chester's less scrutinized, more thoroughgoing privatization had a more troubled first year than did the more measured reforms implemented in Philadelphia, suggesting that a more open political process may yield better programmatic results. The article concludes with empirical and normative lessons about school privatization in urban school districts. Of particular import is that, paradoxically, political factors may force privatization and related reforms to be rushed in ways that make their educational success problematic.