This article unveils the hitherto overlooked tensions between Chile and the International Monetary Fund (IMF) during the formative years of the dictatorship of General Augusto Pinochet (from September 1973 to late 1977). This article shows that ideological affinity between the IMF and Pinochet’s economic team of ‘Chicago Boys’ did not necessarily guarantee fruitful cooperation between the parties. The analysis of this intricate relationship sheds new light on the processes of economic neoliberalization that were conducted in Latin America, with different levels of IMF involvement, between the 1970s and the 1990s. By challenging axiomatic and simplistic approaches of IMF–Latin American relations, this article provides a unique prism to reconsider not only the IMF’s motivations and constraints, but also the proactive modus operandi of its borrowing member-states.