America's educational system has a problem with boys, and it's nothing new. The question of what to do with boys - the "boy problem" - has vexed educators and social commentators for more than a century. Contemporary debates about poor academic performance of boys, especially those of color, point to a myriad of reasons: inadequate and punitive schools, broken families, poverty, and cultural conflicts. Julia Grant offers a historical perspective on these debates and reveals that it is a perennial issue in American schooling that says much about gender and education today. Since the birth of compulsory schooling, educators have contended with what exactly to do with boys of immigrant, poor, minority backgrounds. Initially, public schools developed vocational education and organized athletics and technical schools as well as evening and summer continuation schools in response to the concern that the American culture of masculinity devalued academic success in school. Urban educators sought ways to deal with the "bad boys" - almost exclusively poor, immigrant, or migrant - who skipped school, exhibited behavioral problems when they attended, and sometimes landed in special education classes and reformatory institutions. The problems these boys posed led to accommodations in public education and juvenile justice system. This historical study sheds light on contemporary concerns over the academic performance of boys of color who now flounder in school or languish in the juvenile justice system. Grant's cogent analysis will interest education policy-makers and educators, as well as scholars of the history of education, childhood, gender studies, American studies, and urban history.