On January 8, 1918, President Woodrow Wilson addressed Congress and outlined his Fourteen Points for ending World War I and building a lasting peace. His vision included open diplomacy, self-determination for European peoples, and a League of Nations to prevent future wars. The speech was revolutionary, translated into dozens of languages, and greeted with hope by war-weary populations. But Wilson's vision was fatally compromised by his own contradictions. He championed self-determination while segregating federal offices and supporting white supremacy. He applied his principles only to white Europeans, ignoring colonized peoples who embraced his language. At Versailles, he compromised on everything except the League, producing a punitive treaty that violated most of the Fourteen Points and created resentments that fueled the next war. At home, Wilson's stubbornness and failing health prevented compromise with Senate Republicans. He refused modest reservations that would have preserved American sovereignty while allowing membership in the League. After a devastating stroke, Wilson from his sickbed ordered Senate Democrats to reject the treaty with reservations. The Senate voted down the Treaty of Versailles twice. America never joined the League Wilson created. Without American participation, the League failed to prevent World War II. Wilson died in 1924, his dream in ruins. Yet his ideas survived. The United Nations was built on Wilsonian principles. Decolonization used the language of self-determination. International cooperation became the norm. This episode examines why Wilson's ideals were revolutionary despite his racism, how the gap between vision and reality at Versailles undermined the peace, why Wilson's personality destroyed his own creation, and how ideas can outlast their imperfect authors. It explores the ongoing debates over American sovereignty versus international cooperation, idealism versus realism in foreign policy, and the costs of refusing to compromise in politics. Wilson's Fourteen Points failed in the short term but reshaped the long-term world order.