Throughout its history, the United States has often faced a dilemma: Should it uphold its stated values, or prioritize strategic advantage? In numerous instances, America has chosen to partner with questionable regimes and leaders—decisions justified by the promise of security, influence, or geopolitical leverage. These controversial alliances have ignited passionate debates, both at home and abroad, about whether the ends truly justify the means. This article delves into some of the most infamous partnerships, exploring what drove these choices and the complex legacies they left behind.