In the Introduction, we began to explore the significance of conflict in Schoenberg's thought and that of his contemporaries, noting there its centrality to Freud's model of the psyche and to the mysterious worlds of Kafka's beleaguered personae. In this chapter we explore the role of conflict within Schoenberg's critical and pedagogical writings, characterizing it as dialectical opposition. After an introduction that provides a general context for our inquiry, an historical sketch traces significant precursors to Schoenbergian dialectics by outlining key developments in the history of dialectical thought and adaptations of that thought within musical discourse. The chapter continues by formulating and discussing various categories of opposition as they are used in music theory in general and in Schoenberg studies in particular. The next three sections of the chapter separate Schoenbergian dialectics into three principal areas: dialectics of history, dialectical aspects of musical technique, and “systems” as failed dialectics. Each of these sections centers on close readings of passages from Schoenberg's critical and pedagogical writings. The chapter concludes with a brief discussion of the implications of dialectical thought for future analysis.