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Many who read Maxine Greene’s The Dialectic of Freedom agree that her work provides an inspiring account of imagination as requisite for pedagogies of freedom. Her views on imagination, aesthetics, and education are deeply indebted to John Dewey. However, it is my view that Greene is often viewed as a Deweyan without much further thought or theoretical analysis. It is the hope that this brief theoretical interrogation of her work will 1) clarify the differences between her interrelated views on imagination, freedom, and education from Dewey’s explications on the same subjects, and 2) lend further thought and application of Greene’s – and, in turn, Dewey’s – work as part of philosophy of education graduate curriculums on freedom and imagination.