This paper reflects upon the impact of the sibling histories of parents, their parenting decisions, and the projections and internalization of their difficult sibling dynamics, potentially creating hazards for the children of affected parents. It builds upon and extends the literature of history's impact on individual development and the literature on the importance of sibling circumstances in each generation to include the sizeable effect of both on the next generation. Ultimately, it seeks to examine the multigenerational impact of sibling experience through the study of three case histories, argues for the careful attention to the sibling narratives of parents and children in history taking and treatment, and gives case examples of transcending the past through carefully tailored treatment approaches.