Monetary sanctions are an integral and expanding part of the criminal legal system, even though most of the population under community supervision are indigent. Reentering citizens often leave imprisonment with considerable debt that accumulates from court costs and fees, supervision fees, child support arrears, motor vehicle, and other forms of debt. In this article, we examine how an indigent population of reentering citizens make sense of the totality of their debt, prioritize paying their debts, and develop strategies to increase their personal autonomy within the constraints of family dependence, debt, and state supervision. We track 30 men released from an Alternative Incarceration Facility in Cleveland, Ohio and use case studies to illustrate the strategies men adopted within a set of personal contingencies, including the nature of their debt, the extent of family support, their personal skills and resources, access to jobs, probation requirements, relationships with probation officers, and the exercise of judicial discretion. Our study demonstrates how risk‐taking is baked into the criminal legal system and how this keeps reentering citizens in a perpetual state of carceral vulnerability.
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