When the Spaniards came to settle Manila in 1571 Dionisio Capulong was a young boy. His father was one of the rulers in the region and all were scions of the Muslim royal family of Brunei. The father astutely complied—to a certain extent—with the colonising Spaniards. His son subsequently pursued an ambivalent career alternately working for and rebelling against the Spanish colonisers. Ultimately he became a landowner in the Spanish mode. This is his story. Even from only Spanish reports one can discern great astuteness and opportunism, which enabled the elite to keep local supremacy. Tracing the career of Dionisio Capulong sheds light on the elite in pre-Spanish Manila and environs as well as on Manila's earliest Spanish years.