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The determinants of American grand strategy are in flux. Geopolitically, the post-Cold War unipolar era in which the United States enjoyed unrivaled power is waning on account of China's rise and Russia's resurgence. Domestically, intractable political polarization and the election of Donald Trump are seen as signals that domestic consensuses on American grand strategy are deteriorating. This thesis explores the formulation of American grand strategy during periods of past geopolitical upheaval, so as to gain an understanding useful for asking better questions about its future. The cases examined include the American founding and Washington administrations; the beginning of the Cold War and the Truman administration; and the Clinton administration after the Cold War. This case study comparison utilized Clausewitzian critical analysis to examine if and how the United States has blended different grand-strategy archetypes and balanced integration and insulation at home and abroad. This thesis finds that the Founders and the Truman administration adhered to an "insulationist" paradigm whereby different grand strategy archetypes were blended in order to achieve a balance between integration and insulation. By contrast, the Clinton administration strained this logic in its pursuit of a grand strategy that emphasized integration and eschewed insulation. This thesis concludes with considerations for how the United States may craft its grand strategy for the future.