“Hustlers,” or those who sell often second-hand or homemade goods without licensing or approvals, play a large role in the informal economy, especially in American cities like Chicago. While literature on the informal economy is expansive, there has been relatively little empirical work done on from the perspective of street peddlers in developed countries–creating gaps in the conventional theoretical models of informal work. Using qualitative data taken from interviews with active participants in the “hustling economy” on Chicago’s CTA, I argue that conventional theoretical models of the informal economy, namely the dualist, legalist, and voluntarist,perspectives are insufficient in explaining the complexity and nature of CTA hustlers’ informal work. Using empirical qualitative data, I develop a framework for a theoretical model that addresses the large heterogeneity found in CTA hustlers’ perceptions toward work, their structural and environmental interactions, and their relationship with formalization procedures pushed by the State. This new model, centered around economic and capitalistic failure, serves to broaden our theoretical and empirical understanding of informal work and street hustling in urban American contexts.