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This study examined the extent to which early cumulative risk predicts a range of behavioral and psychological outcomes (i.e., depression, future orientation, risky behavior, educational attainment, and socioeconomic outcomes) measured at ages 15 and 26 and whether executive function (EF) and/or behavioral regulation mediated and/or moderated these associations. Data for this study came from the National Institute of Child Health and Human Development Study of Early Child Care and Youth Development and included a sample of 1,364 participants (52% male) born in 1991 and followed through age 26. Results indicated that early cumulative risk was related to depression and risky behavior at age 15 as well as depression, income, future orientation, and educational attainment at age 26. Furthermore, both EF and behavioral regulation mediated relations among cumulative risk and academic achievement at age 15 and between cumulative risk and income and educational attainment at age 26. Finally, three significant interactions emerged for age 15 outcomes, indicating that EF and behavioral regulation may change relations between cumulative risk and depression, reading, and future orientation. Implications for future research are discussed.