Inspired by the English poet John Keats, W. R. Bion saw negative capability as the most important quality a psychanalyst should have, and, for the patient, as one of the main objectives when undergoing therapy. This negative capability can be linked to the concepts formulated by different authors, including Freud (erogenous masochism), Rosenberg (masochism as gardian of life), De M’Uzan (permanent concern), Press (the building of a passive position), Green (passivity and passivation), Ribas (life passivity), as well as Phillips (being an embarrassment, being lost, or being helpless). Four clinical case vignettes show how negative capability can be lacking for some subjects, notably in its articulation with temporality, making them particularly intolerant to ordinary suffering, as described by Freud, and impeded in the exploration of their internal life. According to Press, it is suggested that soliciting negative capability can reactivate an individual’s fear of breakdown and can, as a result—in the process of therapy—cripple the therapist’s negative capability. The latter will then have to accept to take the place—by transfer—of the defective object in the patient’s mind, so that the null and void negative (« le négatif du non-advenu », Press) is actualized. Finally, we address the factors that—therapist’s education or culture—can foster or cripple the building of their negative capability.