Although I have provided direct services and engaged in litigation related to municipal fines & fees in New York City, monetary sanctions are not my area of legal expertise. Bearing that in mind, I am offering these thoughts in my capacity as a scholar of law, race, and money, and more importantly, as an organizer for economic justice. I hope the essay facilitates constructive conversations about the frameworks we use to analyze the political economy of monetary sanctions and mass incarceration. I am grateful to the UCLA Criminal Justice Law Review and the organizers of “Progressing Reform of Fees and Fines: Towards A Research and Policy Agenda Conference”, hosted at Harvard Law School, for the opportunity to share these reflections.