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This paper revisits and revises the classic sociological concept of middleman minority theory, highlighting its limitations in capturing the realities of immigrant entrepreneurship in contemporary markets. Originally developed to explain racialized hostility toward entrepreneurial minorities positioned between dominant and subordinate groups, the term is not only gendered but also rooted in an outdated and rigid view of race and market stratification. In contrast, we propose the concept of immigrant intermediary entrepreneurs to better reflect the fluid and dynamic roles played by immigrant business owners in today’s neoliberal economy. Building on Fourcade and Healy’s framework of “classification situations,” which describes how contemporary markets operate both as leveling forces and as engines of new social differentiation, we argue that immigrant entrepreneurs no longer simply “bridge” a primary and secondary market but instead must navigate and respond to a much more differentiated consumer landscape. Using novel data drawn from ethnographic fieldwork among Iraqi immigrant liquor store owners in Detroit, a community long-perceived as classic middleman minority entrepreneurs, we show how they creatively position themselves to meet the shifting economic needs and cultural identities of their clientele. Their relative flexibility and responsiveness in providing financial services in the form of check cashing and informal credit (services large corporate retail chains are unable to provide), allows them to act as human intermediaries within a fractured urban economy. This paper offers a conceptual and empirical update to a classic sociological theory, better aligning it with the complexities of migration, markets, and inequality today.