Historical approaches of translation and interpreting studies have variously underscored the cultural, political and diplomatic aspects of the role of interpreters and translators. However, one of the most important duties for the official interpreters called yeokgwan during Korea`s Joseon dynasty (1392-1910), especially in the 2nd half of that era, was to oversee official trade with the Chinese Court (Qing) and the Japanese Empire. Parallel to their official duties they were allowed to trade privately since they travelled to China and Japan as delegation members. Under the rigid social orders - the bureaucrats and literati yangban, the middlemen jungin to which yeokgwan belonged, the commoners and the lowest in one the one hand, and the strict Confucian social rank in the order of scholars, farmers, artisans and tradesmen on the other, yeokgwan were able to accumulate wealth, which helped them to advance themselves socially by devoting themselves to literary works and building up their jungin and specifically, yeokgwan networks e.g. by marriages. On that basis, interpreters gradually enhanced their social status and political power even as the social order became unstable towards the end of Joseon dynasty. This paper aims at illustrating the evolution of the official interpreters during the 2nd half of the Joseon dynasty (i.e. 17-19th Century) by drawing upon translated historical sources like Tongmungwanji (handbooks for official interpreters), the annals of Joseon dynasty and previous research in Korean studies.