In this article I track three ways of confronting the question of whiteness and its attendant problematic of racism. I look at two personal episodes one involving inheritances from white explorer forebearers and the place of racism in fetishized objects and second in the institutional difficulties within psychoanalysis in finding ways to speak about race and the dilemma of being a beneficiary of racism. Finally I look at the hidden racism in a much lauded psychoanalytic article, Joan Riviere's (1929) “Womanliness as a Masquerade,” and in the light of these three problems speculate on “whiteness.” I argue that the intergenerational transmissions of guilt and disavowal together leave a blank psychic space that makes an authentic expression of racial consciousness and genuine reparation currently difficult and certainly, even if well intentioned, partially compromised.