It seems self-contradiction that Laozi wrote Tao Te Ching to demonstrate what was Tao in over 5,000 Chinese characters while he declared what we could assert were not Tao at all. We are also puzzled by his proclamation such as \"The weak one always subjugates the strong one\".How to explain this kind of expression that looks as if illogical but hasits own tongue of reasons? This paper tries to reply this question. The method adoptedis analysis of linguistic context which begin with distinguishing what was the problem Laozi confronted and what was the tactics to solve that problem he drafted, and then judge the meaning within the context of his book should be expressed in fact, thus realize the legitimacy of his paradoxical expression. Key words: analysis of linguistic context, Laozi, paradoxical expression, Taoism, Tao Te Ching.