This paper presents a chronological investigation of Bion's own analytic case descriptions, while comparing them to a close reading of his evolving theoretical writings during those years. It is divided into three parts: Bion before 1967; Bion in 1967-1968, when he launches a radical revision of his psychoanalytic theory and technique; and the late Bion, especially during the last two years of his life. Respectively, it focuses on three of Bion's clinical descriptions, presented in Bion's October 1955 lecture to the British Psychoanalytic Society, and in two of his seminars - the Fourth Los Angeles Seminar (1967) and the Fifth Buenos Aires Seminar (1968); and the account of Brazilian analyst, Junqueira de Mattos, of his analysis with Bion over the final two years of Bion's life. These detailed accounts allow a textual investigation of Bion the theoretician versus Bion the practicing analyst, particularly highlighting the significant gap between them. The author attempts to offer a possible explanation and understanding of this gap between Bion's theoretical and clinical texts, and especially of Bion's long road towards intuiting the patient's suffering.