We know Sun Tzu solely from Sima Qian’s the Historical Records (司馬遷史記). This paper argues that Sima does not think very highly of Sun Tzu, for not only was his biography of Sun Tzu written together with other two ancient generals, Wu Qi (吳起) and Sun Bin (孫 臏), but it focused primarily on his drilling the concubines. To Sima, Herlu (闔閭) was intrigued that a complete outsider could be bold and resourceful enough to con his way into the inner most circle and somehow manage to acquire sensitive information, and Herlu thought such a person was worth investigating and recruiting. Sima implies that Herlu offered Sun Tzu a chance to ease the anxiety of his own generals and that the generals could ridicule his effort of drilling concubines. If Sun Tzu could withstand the joke and earn his stripes, Herlu would offer him a position to keep him in Wu, albeit a minor one to pacify his own generals. Sun Tzu, however, would become an integral component of the king’s army and would wield unassailable power and authority which could not be questioned. Identifying Sima’s reasons for writing this episode will help us to understand his perception of this military guru. We can better appreciate Sun Tzu when we view him not just as an expert in warfare, but as a psychological mastermind as well. Grappling with why Sima writes in such a way as to surprise the readers about this famous military guru is a subject worth exploring.