n Taiwan' s sugar trade during the late Qing dynasty, due to consumer preferences, Anping sugar gradually came to be mostly exported to the region north of Central China, and Takow sugar to Japan. In the past, little attention has been paid to whether these differences in sugar export destinations led Tainan and Takow' s sugar merchants to hold different views on other peoples and on the world, and thus to have different responses to and management strategies for the ceding of Taiwan to Japan. Especially after the 1870s, the group of Takow merchants who personally went to Japan and Hong Kong to conduct cross-national trade transformed Taiwan' s commercial culture in the late Qing period and its historical significance; they are worth examining. Secondly, there is little scholarship on the relationship between the Taiwan' s Governor-General' s Office, which in the early days of Japanese rule faced armed resistance by Han people and had to consolidate its dominance, and those Taiwanese businessmen who had experienced the Meiji Restoration firsthand. Furthermore, Taiwan is an island, and commercial trade has always been the locomotive of economic development. However, how the business strategies and ideas of this group of transnational traders confronted the great changes of this era, changes in which tradition and modernity were intertwined, remains to be studied. How they became political and cultural brokers between the Taiwan Governor-General' s Office and local society, and then expanded their business territory and enhanced their social status are questions even more deserving of attention. This article takes the famous sugar merchant Wang Xuenong, who traded between Taiwan and Japan during the Meiji era, as an example. It attempts to explain how and why this sugar merchant, who had already traded in Japan as early as the Meiji Restoration, adopted different business strategies to expand his business territory and emerged as a major figure of wealth and social status in Tainan at the time when Taiwan was ceded to Japan and many merchants and important clans fled back to China. First, it explains the relationship between international trade and the choice of businessmen either to leave or to stay in Taiwan. Secondly, it demonstrates why Wang Xuenong chose to move from Takow to prefectural capital of Tainan (Fucheng), which was Taiwan' s economic center and largest city, and the initial development of his career. Third, from the perspective of cross-national trade and cultural brokership, it analyzes how he quickly became the richest gentleman in Tainan.