At his peak, Zheng Zhilong commanded a maritime empire so vast that it controlled more sea than land, effectively dictating the terms of all trade and security across the southern waters of China. His career traced an arc through piracy, commerce, military power, and political alliance — accumulating influence through each — before ending in the contradictions of his own defection, when the Qing dynasty he joined eventually executed him for the resistance his son refused to abandon.

His rise through the 14K triad made him one of the most prominent organized crime figures in Macau during the 1990s, a period marked by open gang warfare and a wave of bombings and assassinations that destabilized the territory ahead of its 1999 handover to China. Operating at the intersection of criminal enterprise and legitimate business fronts, he cultivated a public profile unusual for a figure of his kind — most notoriously through a 1997 film that appeared to document his own exploits. His eventual prosecution and imprisonment came to symbolize the broader effort to suppress triad influence in Macau during its political transition.