This paper describes the interlocking economic and political events that took place in Mindanao-Sulu, the Moluccas, and Bornay (Brunei) between the 14th-16th centuries, before the advent of colonization of the region, when they were engaged in the spice trade. During the colonial period, Spain’s colonial policies in the Philippines were considered constrained and influenced by the close relationship between and among these three places. For this purpose, historical sources common to the region that were availed of include the Sejarah Melayu (Malay Annals), Negarakertagama (History of the Madjapahit), and the Suma Oriental of Tome Pires