Influential texts have long identified principals as being essential to school success. Accordingly, high expectations and pressures have attended the principalship and affected the professionals who occupy it. This exploration asked three interrelated questions: What pressures have urban school principals typically faced, in the past and today? What new pressures have emerged? What effects have these pressures had on principals and the prospect for lasting urban school improvement? To answer these questions, historical and contemporary artifacts were analyzed, as well as data from interviews with 17 principals from one large urban district. Findings indicate that today, even more so than in the past, the urban principalship is characterized by extensive responsibilities and limited control, nested in a context of relentless accountability. (Contains 2 notes and 3 tables.)