How do sociolegal scholars who liken monetary sanctions to “bleeding a turnip” or “drawing blood from stones” reconcile these idioms with the fact that fines and fees constitute a growth industry? We take up this puzzle by turning our attention to perhaps the most relatable experience with monetary sanctions among the population: parking tickets. Much of the available law and society literature on fines and fees documents how these sanctions disproportionately impact communities subjugated by race and class. Because parking tickets are adjudicated within a legal domain so fundamentally different from fines and fees that dominate the academic focus, we ask whether these insights extend outside criminal counts to municipal ones. Using Chicago as a case study, our inquiry measures the structural determinants of 11.3 million tickets issued between 2013 and 2017. We use a series of count models to predict the incidence rates of tickets at the tract level as well as how many were subject to reprimands for nonpayment. What we find are disparate patterns of racialization in terms of who is targeted by these sanctions versus who is devastated by them. We synthesize key ideas from empirical critical race theory and developing work on predation theory to make sense of these findings.