In the last decade, educational researchers and scholars have turned new attention to the theory and practice of community organizing as a method for addressing education injustices. While there are diverse traditions of community organizing work, by far the most influential model in US contexts is that of Saul Alinsky, whose "Rules for Radicals" organizer's bible is subtitled "A Pragmatic Primer for Realistic Radicals." Alinsky was not a proclaimed pragmatist in the philosophical sense of that term, but in the "useful and practical" sense. In that vein, his model for community organizing is increasingly used, adapted, and re-formulated by educational activists of many stripes. His work is an inspiration for much community organizing work in education today, which presents on the face of it an interesting contrast to the dominance of the Deweyan pragmatism in curricular and political theorizing in education. In this paper, the author explores whether and how philosophical pragmatism might be a useful tool for achieving educational reform through social action work such as community organizing. The author explores Aaron Schutz's arguments relevant to Deweyan democracy and revisit Dewey's democratic theory to test these arguments. The purpose is not to "rescue" Dewey from Schutz's critique, but to ask a question related to it: whether, and how, can pragmatism be a useful philosophical orientation for community organizing work in the face of today's educational injustices? (Contains 33 footnotes.)