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Reducing energy use is a key imperative for Western societies. However, it is hard to envision how this might come about and what changes are entailed. This article proposes that studying energy history helps understand flexibility in energy systems. It uses the case of Montréal to analyze the fluctuation of electricity and gas supply and demand during an eventful historical period that stretches from the First World War to the Great Depression, marked both by capacity expansion and stagnation. By studying the activities of the city’s monopolistic energy utility and the practices of energy consumers, this article proposes a typology of four different kinds of energy flexibility: upwards supplier-led flexibility, downwards supplier-led flexibility, upwards consumer-led flexibility, and downwards consumer-led flexibility. This analysis has important implications for future energy megaprojects and the shaping of energy consumption. It also shows how energy history can reveal the implications of past patterns for future decisions.