Tsai Hsiang (1012-1067) has been known as one of the ‘Four Calligraphic Masters of the Sung Dynasty’, together with Su Shih, Huang T’ing-chien, and Mi Fu. However, many scholars have pointed out that Tsai’s works are more classical in style compared with the other three’s strong personal touches, and they think that it was political considerations, rather than his dubious art accomplishment, that made Tsai one of the Four Masters. Was he qualified as one of the great four? And how should we treat him as an artist? These questions have been seriously debated since the mid-North Sung Dynasty. This paper would like to discuss the questions from a historical perspective, focusing on the changes of calligraphic styles and the cultural values of the literati between Tsia’s own time and the Ming Dynasty when “the Four Masters” had been well established. We find that Tsai had a profound and lasting influence on calligraphic art over the hundreds of years after his death, and his efforts to promote the status of calligraphy as an art had been greatly appreciated by critics later. In evaluating Tsai’s artic status, we should first get rid of the obsession with pure style examination, place him in historical context, and then his reputation as one of the Four Masters would certainly look more secured.