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The author clarifies the meaning of Winnicott’s concept of a transition object, describes how the growing child uses a transitional object to help tolerate feelings of separateness, and then critiques Pauley’s concept of a negative transitional object (this issue). The importance of the parent’s responsiveness to the needs of the child, the choice of a transitional object as a creative expression of the child’s true self, the use of false self defenses to protect against the parent’s lack of responsiveness, and the role of illusion, paradox, and maternal failure in Winnicott’s understanding of how the child tolerates separateness and develops the capacity to regulate emotions are all emphasized in the critique.