Since Shihabal-Din’s family could not be traced, we could only discuss his career followed by the facts of the southeast overseas trade in the Yuan Dynasty. Shihabal-Din’s story was classified as one of the examples that people become businessmen from officials. This paper mainly discussed and analyzed the background of the times that Shihabal-Din could influence overseas trade development in the Yuan Dynasty, and the reasons and effects why his career was involved with South China Sea, followed by the truths. Shihabal-Din was good at financial development and management. He levied taxes for the government and made financial profits for influential officials when he was an overseas trade official, a local chief executive, and an official of carrying trade division. In fact, Shihabal-Din was highly regarded and protected by the emperor. He failed and got the influence back again, the failure did not impair his influence on overseas trade. However, he abused his power and gained profits for his family. What he did led to criticism. Overall, there are both advantages and disadvantages of overseas trade development in the Yuan Dynasty.