This chapter traces Dr B. R. Ambedkar’s analysis of the “woman’s question” in the context of caste and class. It argues that his thoughts must be located within the diverse positions on the woman’s question that developed in 20th century Maharashtra. Ambedkar belongs to the non-Brahmanical revolutionary stream of thought that had launched an attack on three institutionalized hierarchies: caste, class and patriarchy. He drew explicitly links between the subordination of women and the caste system by highlighting the linkages between endogamy, enforced widowhood and marriage between older men and young girls. This chapter draws out his analysis in detail from his writings and speeches. It critically reviews his position on the caste system and the subordination/enslavement of women to understand the intersection of gender and caste. This chapter underlines how Brahmanical culture denies women the right to knowledge and imposes severe restrictions on them, especially on their sexuality. It also reviews the revolutionary agenda laid down by Ambedkar for the annihilation of caste and emancipation of women. His perspective establishes that women are the gateways to the caste system, to draw attention to the caste-based nature of women’s exploitation and the double exploitation of Dalit women.