This microhistorical account of the understudied Philippine-Chinese leader Albino Z. Sycip explores the many early twentieth-century connections between Shanghai and Manila that he fostered and represented. Coming from an elite background that linked him with influential people in the United States, China, and the Philippines, Sycip built a transnational network of acquaintances. Shanghai became an important node in his network, and through this node, Sycip influenced Sino-Philippine political, economic, and cultural interactions. This article argues that research on Chinese overseas and Chinese and Philippine history could benefit from considering (1) both Filipino and Chinese migrations between East and Southeast Asia instead of only Chinese flows, and (2) overseas Chinese connections to Shanghai in addition to linkages between the Philippines and traditional hometown areas in southern China. Sycip is the glue that binds together this byzantine story of high political encounters, business linkages, and the Chinese community in Manila and the Filipino community in Shanghai.