In 1517, an ambassador from Portugal arrived in Guangzhou. This was the first diplomatic contact between Europe and China of the modern age. However, in 1521, the Ming Court decided to reject the embassy and cut off relations with Portugal. This rejection has traditionally been blamed on the imperialistic behavior of the Portuguese, who acted like typical European colonizers. However, this study argues that the Portuguese often behaved more like Southeast Asian smugglers, and that the Ming Court’s rejection was based on this perception.