Many U.S. schools utilize grade retention (repeating grades when not meeting academic benchmarks) to allow more time for students to learn grade level material. However, some research suggests retention may increase inequalities and not help students progress. We use national data (Future of Families and Child Wellbeing Study 2014–2017) and logistic regression to examine what predicts the likelihood of elementary school retention and whether retention is associated with long term outcomes. We find that race and family income did not predict who was most likely to be retained. As expected, boys were more likely to be retained than girls. Most importantly, we show that, of students in major metropolitan areas, retention did not predict long-term academic outcomes (regardless of race, sex, or familial income). Retention did predict long-term exclusionary discipline outcomes for Black students only supporting the School to Prison Pipeline framework.