Diane Ravitch’s impact on education policy has been and continues to be highly significant. Substantial revisions to her long-held beliefs are reflected not only in her popular blog, but also in two of her more recent books, The Death and Life of the Great American School System (2010a), and Reign of Error (2013). Ravitch’s shift in position has attracted the attention of both progressives and one-time supporters. Each has sought to recast the “new” Ravitch in light of these developments but have often done so unsatisfactorily. This article separates the political and educational aspects of Diane Ravitch and, through analysis of her writings, explicates the language and essential aspects of Ravitch’s thought over time. Having assessed what undergirds both her changing and persistent educational beliefs, progressives and conservatives, along with educators in general, might more aptly contextualize and interpret her positions in current reform debates.