Winnicott found that loss occurring during the time of a child’s immature emotional development results in illness. This illness forms a deprivation that leads to a reaction in one’s environment. Through stealing and destruction, the child makes a demand on his environment to reclaim what has been lost. This paper explores Winnicott's conceptualization of the antisocial tendency and the role played by deprivation. Speaking from his experiences of working with a child patient in foster care for nearly 12 years, the author discusses his provision of a maternal environment. The foster care system in a large Midwestern city, intersecting with race and class barriers are also explored.