Analyses addressing 2 sets of hypotheses were examined. First, it was hypothesized that the number of parenting transitions would define a continuum that would covary with the magnitude of the adjustment problems experienced by boys in the family. Intact, single-mother, stepfather, and multiple-transition families were selected from 206 predominantly lower- and working-class families in the Oregon Youth Study and compared on a comprehensive measure of boys’ adjustment at Grade 4. Boys who had experienced multiple transitions showed the poorest adjustment. This relationship was still significant after controlling for socioeconomic status (SES) and per capita income. In the 2nd set of analyses, the hypothesis that maternal antisocial behavior (MAB) contributes directly to relationship transitions and indirectly to child adjustment problems was tested in a structural equation model. A mediational model including MAB and parenting practices was used to predict child adjustment measured 2 yrs later. Number of transitions was highly related to MAB. The antisocial mother was most at risk for transitions and unskilled parenting practices, which in turn placed her son at risk for poor adjustment.