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In this study, we advance research that examines class heterogeneity among South Asian Americans in the U.S. We focus specifically on as-yet unexplored within-group distinctions within the “Asian Indian” ethno-racial category: namely, the distinction between “Asian Indians” from the Indian subcontinent and Indo-Caribbeans – people of “Asian Indian” descent whose immediate ancestors hail from the former colonies of the British West Indies. Although Indo-Caribbeans were the first, and -- until 1964 -- the largest South Asian population in the New World, Indo-Caribbeans they remain practically invisible in U.S. scholarship. This is due, both to Global North stereotypes that imagine the Caribbean as an exclusively Afro-Diasporic space, and to an overwhelming tendency to study Asian "model minority" experiences. Even though Indo-Caribbeans are the demographic majority in Trinidad and Guyana (the two largest British Caribbean societies after Jamaica) and though they constitute 20% of the British Caribbean's total population. Unlike South Asian Americans, who are often class-advantaged, and who migrated to the U.S. after the 1965 Hart-Cellar Act, Indo-Caribbeans descend from the first and largest Asian indentured labor population brought to the New World. In this study, we examine how these different starting points impact Indo-Caribbean and South Asian socio-economic incorporation trajectories. In so doing, we demonstrate how colonial history and 20th century immigration policies drive severe class stratification among "South Asians" in the U.S.