The school-to-prison pipeline, or the relationship between school discipline and juvenile justice contact, has interested researchers and educational practitioners primary because of the negative impacts punishment can have on the life outcomes of students. Using a unique dataset of matched school and juvenile justice data, this dissertation challenges the “pipeline” or uni-directional flow of youth punishment and finds that punishment operates in a cycle. In three chapters this dissertation examines (1) when students face suspensions and juvenile justice contact, (2) the relationship between suspensions and juvenile justice contact, and (3) tests the theoretical explanations of the relationship of youth punishment. Generally, I find black and Latinx students have higher risks of youth punishment in all grade levels, but most importantly early grades, and that while a school suspension increases the chances of juvenile justice contact, students also have increased odds of subsequent after juvenile justice contact. Evidence of critical race, cumulative disadvantage, and labeling theories support a new theory that youth become caught in a “cycle of punishment” rather than a school-to-prison pipeline.