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In this paper, we use newly available data from the National Longitudinal Survey of Youth to investigate the effects of early motherhood on academic and behavioral outcomes for children born to early childbearers. We find that early motherhood's strong negative correlation with children's test scores and positive correlation with children's grade repetition is almost entirely explained by pre-birth individual and family background factors of teen mothers themselves. However, early childbearing is associated indirectly with reduced children's test scores through its linkage to family size (and thus to child birth order). We find a different pattern in predicting fighting, truancy, early sexual activity, and other problem behaviors among adolescent and young adult off-spring. For these behaviors, maternal age-at-first-birth remains an important risk-factor even after controlling for a wide range of background factors and maternal characteristics. These results highlight the diverse pathways through which teen parenting might influence subsequent child well-being and social performance.