This book examines changes in American grand strategy, particularly in foreign policy engagements with the world, throughout its history. The study surveys and analyzes the development of American self-government from 1620 to 1787 in order to develop the fundamental political theory that serves as the foundation for the Declaration of Independence and the Constitution, as America's first grand strategy. A thorough critical analysis is also conducted on the historical continuum of American grand strategy since 1776 through the lens of grand strategy and American political theory. Case studies on three distinct wars are included in the analysis and criticism: the Mexican-American War, the Philippine-American War, and the Vietnam War. The purpose of this criticism is to evaluate the effectiveness of the means utilized by America's grand strategy to maintain the balance between liberty and order in both domestic and foreign policy, with particular emphasis on the foreign policy traditions that have shaped American grand strategy. . Finally, critical lessons are applied to frame an effective 21st century American grand strategy in the wake of Afghanistan and Iraq.