In November of 1903, the United States, under the leadership of Theodore Roosevelt, helped protect and support a revolutionary movement on the Panama isthmus. As the region seceded from its mother country, Colombia, the world stood in both shock and celebration. The story that is normally explained afterward focuses on the building of the Panama Canal and the U.S. rise as a dominant world power. But what about Colombia’s experience? For the South American country, they lost a priceless territory in a humiliatingly public event. More strikingly, before this Colombia and the U.S. had shared a long and cooperative relationship throughout the previous century, and now this close friendship was tarnished in an instant. Instead of moving their separate ways, the governments of each nations unexpectedly went to great efforts to salvage what was left of this broken relationship over the following two decades. For the first decade ordinary circumstances made hope of a settlement a dismal affair, but monumental changes soon took place with the outbreak of World War I in 1914 which inverted the political and economic atmospheres of not only Europe, but the Western Hemisphere as well. Owing to the War’s massive influences, the U.S. and Colombia would finally find motive to rekindle their ties. This essay dives into this tumultuous situation between the two nations and explains why, and how, a relationship fragmented by deceit and aggression was able to be redeemed during the most destructive conflict the world had ever seen.