Even though Operations Iraqi and Enduring Freedom have created a surging trend of research and literature connected with irregular warfare, there is still inadequate study and appreciation of the United States commitment in the Philippines at the beginning of the twentieth century. Despite a rapid Spanish defeat in the Philippine theater during the 1898 Spanish-American War, America would fight a difficult and complex insurgency in the islands until 1902, and beyond. The decisions and actions of key American civilian and military leaders throughout the Philippine-American War provide valuable insight to defining victory in the current and future irregular wars that America must fight. This monograph identifies and examines three key objectives, whose achievement laid the foundation for America's claim to victory during the Philippine-American War. Additionally, by relating these objectives to the 2003 war in Iraq, this monograph proposes that America has a historically supported claim to victory in the Iraq War.