Early adulthood represents a period of transition that is marked by change and exploration. For some, this transition is uncomplicated, yet for others, it is problematic. While many studies have explored factors that predict adjustment in childhood and adolescence, substantially less is known about childhood factors that predict adjustment during the transition into adulthood. Furthermore, it remains unclear whether childhood factors that predict adult adjustment differ between African American and Caucasian males. Accordingly, the current study examined childhood predictors of early adult (age 19–20) adjustment in a community sample of 397 African American and Caucasian males. Findings indicated that African American and Caucasian males who experienced high levels of peer delinquency, depressive symptoms, and conflicted parent–child communication in childhood were more likely to experience adjustment issues in early adulthood. For African American males, low academic achievement was important for predicting adult adjustment, while low organization involvement uniquely predicted adult adjustment for Caucasian males.