董其昌書學觀點存在著對「熟」與「生」、「合」與「離」、「正」與「奇」、「法」與「意」等辯證性探討。透過這些觀點，除了清楚呈現他在書法藝術上的審美指標外，他也多次以趙孟頫為反例，藉著對趙孟頫書法的批評，凸顯自己在書法論述上的合理性，然而藉著趙、董間的反差，更可看出兩者所分別標幟的典範類型。本文從董其昌對趙孟頫的評述為起點，深究董其昌以「淡」為宗的核心思維，導出以「形」求「神」的藝術境界，凸顯出董其昌在書學觀念上「尚意」的特質；論文架構上分別以「董其昌書論中以趙孟頫為反思的書學觀點」、「董其昌書論的核心思想：求淡──由形到神」、「董其昌書學的時代意義：重現意的深度」等三大主軸，探討董其昌書學審美的核心思維，及其書學在書法史上的意義。

Dong Qi-Chang’s argued and discussed the concepts of calligraphy through the following indicators: i) skilled vs. unskilled, ii) compatible vs. incompatible, iii) traditional regular script vs. rare script, and iv) standardized strokes vs. free-spirited strokes.Through these indicators, Dong not only demonstrated his ways of evaluating the beauty of calligraphy, he also criticized Zhao Meng-Fu’s calligraphic work in order to strengthen his arguments. From Dong and Zhao’s contrasting work, one can notice the differences between the two calligraphers’ emblems regarding classic calligraphy. From Dong’s criticism towards Zhao, this article discusses Dong’s core values on how he viewed calligraphic aestheticism- starting from holding plain and celibate-liked thoughts, then producing each script on paper, and finally finding verve in the written script. The article discusses Ming Dynasty’s aesthetic changes in calligraphy from Dong’s three main concepts: i) Using Zhao’s work to establish Dong’s calligraphic viewpoints, ii) Illustrating Dong’s core values: simplistic thoughts, script formation to verve in calligraphy, and iii) Studying Dong’s significance: rediscovering the depth of free-spirited script in calligraphy.