This book is about the practice of grade retention in elementary school, a particularly vexing problem in urban school systems, where upward of half the students may repeat a grade. On the Success of Failure addresses whether repeating a grade is helpful or harmful when children are not keeping up. It describes the school context of retention and evaluates its consequences by tracking the experiences of a large, representative sample of Baltimore school children from first grade through high school. In addition to evaluating the consequences of retention, the book describes the cohort’s dispersion along many different educational pathways from first grade through middle school, the articulation of retention with other forms of educational tracking (like reading group placements in the early primary grades and course-level assignments in middle school), and repeaters’ academic and school adjustment problems before they were held back.