This study assesses the effects of Head Start participation and demonstrated academic ability during elementary school on School-to-Work (STW) program participation. The study sample comes from the National Longitudinal Survey of Youth, 1997 Cohort and comprises 4,370 adolescents who reported grades they received while in the 8th grade and whether or not they ever repeated a grade in grammar school. Findings indicate that STW programs attract disproportionate numbers of students with histories of marginal demonstrated academic ability. This is so because STW programs are also more likely to attract Head Starters. Demonstrated academic ability varies by race/ethnicity and sex, with lower participation rates by white males. The author suggests that efforts to achieve a more heterogeneous racial/ethnic mix of students to take advantage of school-to-work based initiatives would strengthen such programs. In doing so, such efforts would increase the prospects of Head Start participants entering the mainstream of socioeconomic life in the US more easily than would be the case otherwise. In addition, such efforts would make the US workforce more competitive in an increasingly global economy.