Through a comparative analysis of James Legge’s and Zhao Yanchun’s English translations of Zhuangzi, this study explores the manifold embodiments of the translator’s subjectivity in cross-cultural translation and the impact of such embodiments on the dissemination of philosophical ideas. Focusing on the linguistic and ideological dimensions, the study combines comparative and case study analyses to reveal the differences in the strategies of the two translators in terms of lexical choice, syntactic reconstruction, and philosophical interpretation. The differences between the two stems from individual linguistic ability, the context of the times, and the purpose of translation–Legge’s translation served the establishment of Western missions in the nineteenth century, while Zhao Yanchun stood in the context of globalization and promoted dialogue between cultures. This study provides a new perspective on translation theory, reveals the paradigm shift from “knowledge introduction” to “value regeneration” in the translation of Chinese classics, and emphasizes the key role of translator’s subjectivity in translation.