Translated from Enchiridion of Epictetus, a manual of Stoic ethical advice, Matteo Ricci’s Twenty-Five Sayings was shaped by the cultural context of Late-Ming China. Though an essay of limited length, the Twenty- Five Sayings actually is a confluence where heterogeneous thoughts from East and West, including ancient Greek and Roman Stoicism from the original text, traditional Chinese Confucianism from the target text, as well as Christian teachings which the translator Matteo Ricci managed to infuse. During the process of translation, Matteo Ricci incorporated the two kinds of “pagan” wisdom—Stoicism and Confucianism — and used them for the purpose of his own Christian mission. This paper investigates how the translator constructed his target text by reviewing on chapter of Twenty- Five Sayings. Furthermore, it explores how Chinese readers in the Ming and Qing dynaties understood or misunderstood Matteo Ricci’s Twenty- Five Sayings. By examining the translator’s mechanism of translation and the readers’ reading experience, I hope to uncover how the new and the old, the same and the different wove together during translating and reading in the process of trans-cultural communication.