This chapter examines the transition of Wilfred Bion from troubled First World War veteran to innovative psychoanalytic thinker during the Second World War and its aftermath. It draws upon the recently published letters by Bion to John Rickman.1 The material is a collection of 29 letters, 27 from Wilfred Bion to John Rickman, one addressed to Mrs Rickman and one from Rickman to Bion (Vonofakos and Hinshelwood 2012).