Elephants have played a key role shaping land and life in South Asia, bound up with human enterprises of power, wealth, worship, pleasure, and preservation. Not just representing weapons of war, emblems of prestige, commodities for exchange, or symbols of divinity, elephants can also be companions, pests, and victims. Deep histories of collaborative and conflicting interspecies entanglement extend into the present, where the effects of industrial modernity impose ever greater strain on our increasingly beleagured relations with captive and free-roaming elephants. Adored and deplored, pitied and admired, the elephant has become a figure reflecting the existential tensions and challenges of cohabitation in a crowded world of demographic expansion, technological development, and economic activity. Human civilization has produced toxic environments and fragmented habitats that increase and exacerbate conflict with elephants. Similarly, for today’s captive elephants, South Asia is a place where elephants are no longer used or valued in the same ways or to the same extent, leaving many unemployed, undervalued, and poorly cared for. Responding to these related dilemmas, drawing on the concept of the anthropocene, and adopting a multispecies perspective, this paper considers the future prospects for the elephant in South Asia, and how we might better learn to live well together.