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Drawing on biographical and autobiographical material and my own experience as an ex-analysand and boarding school survivor, I examine the life and work of Charles Rycroft through the lens of ‘British upper-class complex trauma syndrome’. I argue that the frustrations, anger, and disillusionment of Charles within the British Institute of Psychoanalysis - from which he eventually with drew - can be explained if we see him as being badly let down by a psychoanalysis which could not comprehend his ‘complex trauma’ (echoing his upper-class childhood and boarding school experiences), which fell outside the orthodoxies of infantile sexuality and the Oedipus complex. I also draw on the pioneering work of trauma expert Judith Lewis Herman, psychotherapist Nick Duffell, and Jungian analyst Joy Schaverien in identifying the syndrome. The piece ends with a plea, via a sympathetically re-evaluated Charles, that psychoanalysts and psychotherapists broaden and deepen their vision and protest against familial regimes and social institutions which fail to recognize or rupture attachment needs - particularly of children - and a call for remedial action.