Reconstructing the historical interplay of wildlife and pastoralists in the African savannas is clouded in contemporary studies by the transformation of subsistence societies and land use changes. We draw on five decades of monitoring by the Amboseli Conservation Program to illustrate the rainfall–-plant–herbivore linkages in a free-ranging wildlife–livestock system transitioning to contemporary savanna landscapes. In half a century, the coupled interactions of wildlife and livestock in the Amboseli ecosystem driven by rainfall and water sources have been severed and reshaped by farming, land subdivision, sedentism, poaching, and intensified herbivory. Livestock ranges have expanded, wildlife ranges have contracted, and overlapping spatial use has fluctuated with population sizes. In contrast, wildlife and livestock herds have been sustained where the rangelands remain open. A decrease in the mean body size reflecting a shift to small stock among pastoralists has increased species dominance, decreased diversity, and elevated biomass turnover and the probability of extreme shortfalls. In recent droughts, pastoralists have been importing food supplements to reduce drought risk and purchased livestock to restock herds, further uncoupling the rainfall-herbivore link. Our study reinforces the view that biomes worldwide are shaped at an accelerating pace by human agencies rather than endogenous environmental factors. Disputes over models of rangeland systems echo the wider debate over using natural ecosystems as benchmarks for conservation verses “gardening” nature. We argue that models of natural ecosystems fail to account for the dominant role of humans in contemporary ecosystem yet that it is possible to monitor the complex interplay of human and natural systems and interpret the changes in terms of ecological function using macroecological analysis. The key finding for conservation is the importance of space, landscape heterogeneity, social networks, and mobility in sustaining the large herbivore populations.