In 1593, the Chinese and Japanese armies fighting in Korea in the Imjin War (1592-1598) settled down and began negotiating for a peaceful solution to end the conflict. Yet the three year long negotiations came to be plagued by deception and misrepresentation made purposely by the negotiators to their respective sovereigns, culminating in the Chinese investiture of Toyotomi Hideyoshi as the vassal King of Japan in 1596, which to the Chinese was considered an honor but was an insult to Hideyoshi himself, who promptly sent his troops back to Korea to renew the invasion. This paper studies the problems faced by the lead negotiators which forced them to rely on deception, focusing on the issue of the Chinese perception of others as uncivilized, the political superstructure that was built around that perception, and how Hideyoshi attempted to challenge the Chinese world order in his approach to diplomacy.