This article presents the findings of a qualitative study of four middle school principals in one urban school district. It focuses on principals' almost exclusively negative descriptions of the families and communities served by their schools. Whereas much previous writing on this topic has attributed such deficit attitudes to a few bad-thinking educators, this article argues that these principals' beliefs are in fact aligned with prevailing attitudes about urban communities, the purposes of schooling, and what leadership can and should do in urban schools. Remedying principals' deficit frameworks is a prerequisite for school improvement and will require selecting, preparing, and supporting principals differently; it will also require making visible the systems of belief that obstruct connections between urban schools and communities. (Contains 2 tables and 14 notes.)