Biographical references to Winnicott's analysis of Masud Khan provide the background for this exploration of Winnicott's and Khan's conflicts about disillusionment. On the basis of historical data, speculative hypotheses are presented about possible sources of Winnicott's difficulty engaging Khan's hate and destructiveness. Winnicott's feelings about Khan may have been influenced not only by his denied disillusionment with his own father and his analysts, James Strachey and Joan Riviere, but also by the impact of Strachey's covert anti-Semitism.