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The author investigates the clinical affinity between Klein and Winnicott (1935-46) as a way to historically situate Winnicott's later criticism of Klein's ‘temperamental’ inability to understand the impact of the environment on the infant's development. By setting out Klein's theories at the time when Winnicott began supervision with her in 1935, a context is established for the analysis of an unpublished 1937 manuscript by Klein (‘Notes on baby’). The author argues that this direct and extensive infant observation demonstrates Klein's sensitivity to the familial environment. While Winnicott as a paediatrician showed enthusiasm for Klein's ideas, he also demonstrated a difference of opinion in emphasising the maternal environment of provision after his wartime evacuation experiences with London children. The factors leading to their mutual distancing are outlined as follows: (1) the post-Controversial Discussion atmosphere of the British Psycho-Analytical Society in 1944. The new non-aligned psychoanalytic ‘middle group’ allowed Winnicott to take a pick and choose attitude towards available analytic theories; (2) Winnicott's new clinical practices and theory differed from Klein's, leading to a widening gap between 1946 and 1951. Winnicott's new theory and practice simultaneously represented his technical marginalisation of Klein's emphasis on the direct analysis of the patient's destructiveness by the time he delivered the ‘Transitional objects’ paper in 1951.