If you are referring to the United States, the answer is probably the Vietnam War.
According to Machiavelli's the Prince, princes should act in a practical manner. Machiavelli produced a practical guide to the arts of statecraft, which served the practical needs of the powerful families that emerged in the Italian city-states during the Renaissance. Statecraft involved carefully crafted approaches to the realistic conditions faced by rulers. It was driven less by emotion or morality but reason.
Answer: Robert Parris "Bob" Moses
Hope this helps