Wilhelm Reich and Donald Winnicott were contemporaries who offered radical challenges to the theories and techniques of classical psychoanalysis and to the child-rearing practices of their times. They shared deep and abiding interests in the world of the mother/infant dyad and the fundamental interrelatedness of mind and body. In spite of numerous theoretical parallels, their writings show no evidence of familiarity with each other’s work. This chapter will explore how the work of each is enriched by the perspective of the other.