College students who report a history of childhood maltreatment may be at risk for poor outcomes. In the current study, we conducted an exploratory analysis to examine potential models that statistically mediate associations between aspects of maltreatment and aspects of academic outcome, with a particular focus on executive functions (EF). Consistent with contemporary EF research, we distinguished between relatively “cool” EF tasks (i.e., performed in a context relatively free of emotional or motivational valence) and “hot” EF tasks that emphasize performance under more emotionally arousing conditions. Sixty-one male and female college undergraduates self-reported childhood maltreatment history (emotional abuse and neglect, physical abuse and neglect, and sexual abuse) on the Childhood Trauma Questionnaire (CTQ), and were given two EF measures: (1) Go-No-Go (GNG) test that included a Color Condition (cool); Neutral Face Condition (warm); and Emotion Face condition (hot), and (2) Iowa Gambling Task (IGT), a measure of risky decision making that reflects hot EF. Academic outcomes were: (1) grade point average (GPA: first-semester, cumulative, and semester concurrent with testing), and (2) Student Adaptation to College Questionnaire (SACQ). Correlational patterns suggested two EF scores as potential mediators: GNG reaction time (RT) in the Neutral Face condition, and IGT Block 2 adaptive responding. Indirect effects analyses indicated that IGT Block 2 adaptive responding has an indirect effect on the relationship between CTQ Total score and 1st semester GPA, and between CTQ Emotional Abuse and concurrent GPA. Regarding college adaptation, we identified a consistent indirect effect of GNG Neutral Face RT on the relationship between CTQ Emotional Neglect and SACQ total, academic, social, and personal–emotional adaption scores. Our results demonstrate that higher scores on a child maltreatment history self-report negatively predict college academic outcomes as assessed by GPA and by self-reported adaptation. Further, relatively “hot” EF task performance on the IGT and GNG tasks serves as a link between child maltreatment experiences and college achievement and adaptation, suggesting that hot EF skills may be a fruitful direction for future intervention efforts to improve academic outcomes for this population.