This study explores the calligraphy and the cultural achievements of the cultural figure Ding-Shan Chen who arrived in Taiwan in 1948. Before arriving in Taiwan, Ding-Shan Chen has been a celebrity with a literary reputation in Hangzhou and Shanghai and he has participated and hosted numerous innovative cultural business. However, after the arrival in Taiwan, the situation changed and he became ordinary. It is worthy to explore the causes. From the perspective of hermitage in the ordinary world, this study interprets the special position of Ding-Shan Chen among the literati who arrived in Taiwan. The praises of “graceful” and “godly” from Shou-Po Tao and Hu-Fan Wu for Ding-Shan Chen, respectively, are consistent with the special position of Ding-Shan Chen. The writing style of Ding-Shan Chen was mostly recognized by his similarity to that of Dao-Zhou Huang. However, it cannot demonstrate all his cultivation. Thus, based on various literatures and new publications, this study attempts to generalize the academic process of Ding-Shan Chen and his relationship and supplements and revises the achievements of Ding-Shan Chen in Shanghai written by Ju-Lai Chen.