Bion and Winnicott proposed distinctive images of infancy and the infantile, which reflected their more general theoretical and clinical tendencies, each evolving from Melanie Klein’s emphasis on object relations. Winnicott went further in prioritizing both object relations and the actual environment while rejecting the idea of the Death Instinct and the paranoid-schizoid positions: His view of the infant–mother relation emphasized interpenetrating, shared, and relatively comfortable presence. Although Bion introduced an important role for the mother in transforming potentially disorganizing “bad” projections, he stayed closer to Klein’s model in featuring frustration and its management as a primary source of normal development. The difference between Winnicott’s “holding” and Bion’s “containment” is clarified: Holding connotes a more mutual and harmonious arrangement, while containment implies that there is something potentially disruptive to contain. Clinical implications are noted.