This is a critical essay exploring the problems of translation through the actual cases of two prominent English and American translators, Brother Anthony and David McCann, who are well known for translating modern and contemporary Korean poets’ works. This essay reviews and compares their translations of works by Seo Jungju, Ko Un and Shin Kyongrim, who represent contemporary Korean poetry and also appeal to Westerners most. Pointing out not only the errors and awkward expressions but misunderstanding and insufficient grasp of the meaning of the poems in these translations, this essay offers alternative possibilites for revision and improvement. The problem of translation is centered around the issues of faithfulness and readability. Benjamin suggests a third realm beyond these two, which we have yet to attain with much effort. Yet there is another significant problem of translation reflecting interrelationship between two different cultures. Collaboration between a native literary scholar and a foreign translator is one way of closing the cultural gap between the original and translated texts. Here, it is important for the critical input of native literary scholars to be actively reflected in the translation process.