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Despite renewed scholarly interest in the role of leaders in international relations and how their disposition and beliefs affect policymaking, questions remain over the extent to which these variables are subject to change over a leader’s time in office. This study looks at three key foreign policy events from Margaret Thatcher’s premiership – the Falklands War, the United States invasion of Grenada and the US bombing of Libya in 1986 – through the lens of rigidity and flexibility to explain how Thatcher’s later decisions were influenced by earlier events. Drawing on archival and biographical sources, it argues that the response of the Thatcher government to the US invasion of Grenada and the subsequent political fallout challenged Thatcher’s worldview in a way the Falklands War did not. Thatcher’s reassessment of the Anglo-American relationship ultimately expanded the range of acceptable policy options when it came to the 1986 air strikes against Libya. This analysis contributes to the political leadership literature by demonstrating how experiences in office changed Thatcher’s approach to future foreign policy crises. It also demonstrates the utility of combining archival research with the insights of political psychology, emphasizing the situational and dispositional factors that influence the decisions leaders make. Finally, it highlights the US invasion of Grenada’s impact on British politics; previous research on this period in British political history has acknowledged Grenada’s short-term impact on Thatcher and President Reagan’s personal relationship, but this study reveals its long-term impact on Thatcher’s worldview was far greater than previously recognized.