The seductive pull of gambling lingers in the mind, a promise of fortune wrapped in the thrill of risk. Casinos have long served as carefully regulated arenas for this pursuit, yet Illinois’ Rebuild Illinois initiative, passed in 2019, ushered in a new era of unrestricted casino expansion, including Wind Creek Chicago Southland. Through a combination of ethnographic research and interviews, this paper examines the intersection of policy, addiction, and personal experience at Wind Creek. I found that the casino’s reward structures and incentive systems encourage repeated play, drawing both casual visitors and seasoned gamblers into cycles of loss and pursuit. While some patrons praised the casino as a social hub, the shadow of addiction loomed larger, reinforced by the psychological mechanisms of slot machines and tiered reward programs. These findings suggest that Illinois’s new gambling infrastructure may inadvertently serve as a structure for addiction. If left unchecked, this structure may continue, if not expand, how people can engage in casinos that fuel addictive behaviors.