Should the US grand strategy be one of leaning forward or one of pulling back? Or are the US interests best served by a strategy situated midway between lean forward and pull back? An intense debate continues over what kind of grand strategy the United States should pursue in order to best preserve its national interests. And consequently, there is also a major debate about how America’s interests should be defined. However, these debates are not new. They have been waged since the United States gained its independence, and they have passionately continued into the early 21st century. These debates have been flamed by various traditions of US foreign policy and by changes in the structure of the international system, as well as by the different interpretations of the US past. Intellectuals, historians, policymakers, and scholars of international relations (IR) have vigorously engaged the issue of grand strategy, its definition, and even its usefulness. IR scholars still wrestle about the criteria to classify grand strategies and about the consequences that various grand strategies could have for the US future. Given all these factors, this article is structured as follows: (1) it defines and presents a general view of grand strategies (see Defining Grand Strategy and Grand Strategies: General Overviews), (2) it presents the reader with a Taxonomy of Grand Strategies, and (3) it presents US Grand Strategies in Historical Context—and the debates that surrounded them—from World War I to the early 21st century. Given its forward orientation, this article gives more attention to debates that took place after the Cold War.