Western societies exact a tall order on women who choose to have children. Western norms include an unspoken critique of working women: Are you someone who prioritizes paid work over child caregiving, or do you prioritize child caregiving over work? This double objectification of women who are mothers is their double jeopardy. Although there are multiple jeopardies for those who are not of the dominant caste, for women, the greatest second jeopardy is that of a mother. I outline the jeopardy of being a woman in Western societies, focusing on the history of demonization, including a brief discourse on how psychiatry has perpetuated this demonization. I give historical reference to exceptional women of courage and strength, women who have not yet reached the public imagination. I outline the history of the idealization and vilification of mothers and its reach into the practices of parenting. I propose some solutions to resolve the problem of double jeopardy.