This article examines the activities of Tan Kah Kee in China and Singapore from 1949 to 1950 when Tan's role changed from that of leader of the overseas Chinese to chief representative of the overseas Chinese, to representative of New China, and finally to representative of the returned overseas Chinese. It argues that Tan continued to hold on to his ideas despite the changes in his roles. He went to China without the intention of never revisiting or returning to Singapore. He rarely criticized the British as he did the Americans. Almost all his proposals were still related to the reform of social habits and public health in overseas Chinese society. In continuing to hope that the new government in China would facilitate interaction between the overseas Chinese and China, Tan thus entertained hopes for the overseas Chinese to remain free to move between their place of domicile, China and even Britain.