This article studies the strategic journeys of two Indian banks in evolving socio-political and economic environments, spread across eight decades. It provides a holistic view of longevity challenges by exploring interdependencies between a firm’s internal dynamics, external environment, and its leaders. This article covers the growth of Canara Bank and Syndicate Bank in distinct phases of unrestricted, regulated, and centrally planned economic environment, and in changing socio-political scenarios. It uses within-case and across-case analysis, contextualised in these conditions, to provide rich insights about measures adopted by firms for their long-term survival and sustenance.