Despite India’s three decades of economic liberalization, access to quality education, well-paying jobs, and high standards of living align with prior class and caste advantages, leaving many poor and working-class people stuck in place and obligated to seek handouts from the rich. The study draws on ten years of ethnographic fieldwork at three private golf clubs in Bangalore, India’s Silicon Valley, to explore the ties of dependence wealthy club members generate with the poor lower-caste golf caddies who carry their bags, and in a manner that reproduces their positions of privilege and authority. The caddies are not employees, and yet neither do they have complete control over their rates and schedules. Making $3–5 for a five- or six-hour round, caddies deploy acts servility and deference to yield additional money for healthcare, children’s school fees, and other household expenses. While a rare few caddies win sufficient support to put them and their families on a path of social mobility, most struggle to make ends meet, living in less-than-secure housing, going without food in some cases, and sending their children to low-quality schools that all but guarantee they will take up similar work as their fathers. The necessity but ultimate limitation of such relationships between the rich and poor underscores the failure of India’s development strategy, which favors private over public interests, and has yet to establish well-funded healthcare, education, and basic social services that would improve chances of social mobility and independence among the poor.