Malcolm X in his autobiography claimed that every experience he had as a youth was educative. Such a claim confronts us, as educators, with a serious dilemma, that is, whether all transformations and human experiences are educative. In reviewing John Dewey's major writings on the topic, the author concludes that some of Malcolm X's early experiences were not educative although his re-education through the instrumentality of the Nation of Islam served him well as an educative experience because it liberated him from the destructive rendition of the social order.