Many Chicagoans are getting shortchanged, particularly when it comes to money exchange between the Illinois Lottery (IL) and Illinois State Board of Education (ISBE). A significant portion of lottery sales is earmarked for education in Illinois. Because these revenues are not generated equally, however, some contribute more to education via the lottery than others. When this money is distributed in a way that transfers it from one community to another, one community's fiscal gain comes at another's expense. So the question stands: Who plays and who pays? To answer this question, I use the city of Chicago as a case study to simultaneously compare the generation and appropriation of lottery revenues. What I found was that this exchange is inherently organized along lines of race and class. Lottery revenues disproportionately come from communities comprised predominantly by people of color and the working class, and then are redistributed across all communities through education finance. When fiscal policy of Illinois public education is structured in such a way, it inequitably distributes economic capital and preserves undeserved enrichment and unjust impoverishment. This represents a state-sponsored process that captures one mechanism for the reproduction of race and class inequality.