Though a very refined process that usually employs well-tested strategies and strives for realistic goals, the undertaking of international diplomacy is never guaranteed any measure of intermediate or ultimate success. In the geopolitical matrix, too much can go wrong when human wills are called on to make critical decisions that may amount to moral imperatives or political expediency. As seen recently, sensitive negotiations to rescue Canadian nationals held captive by Filipino insurgents ended tragically in two of them being beheaded. Such an outcome may be seen as a failure because the all-important line of communications, or channel through which information is shared, broke down. Since both sides depended on each other to deliver, in a timely fashion, something that moves the negotiations along, any delays were construed as a serious breach of trust leading to the captors giving up on ever receiving payment for the release of the captives. Then there is the situation where negotiations meet an impasse, as in the case of President Woodrow Wilson’s inability to sell the European powers at the Versailles Conference on the need to sign a general covenant that respected the national sovereignty of all nations. Diplomatic failure was likely the result of no back-up position being available on both sides to extend negotiations. While many historians and diplomats of the period blame Wilson’s idealistic inflexibility for this pivotal clause being scuppered, I choose to see it as the ideal European powers of Britain and France not being prepared to accept it at that time. Wilson realized this and walked away from the conference, realizing that his original 14 Points were doomed without agreement on this issue of national autonomy.