The purpose of this paper is to examine the relations between two pro-American intellectuals: Japanese Asakawa Kan’ichi (1873–1948) and Chinese Hu Shih (1891–1962). Graduating from Tokyo Senmon Gakko (now Waseda University) at the top of his class in 1895, Asakawa Kan’ichi continued his education in the US where he studied the history of law. Asakawa earned his Ph.D. in history from Yale University in 1902, becoming the first Japanese professor at Yale University. He is known as a pioneer of comparative legal history, especially comparative history of feudal societies in Japan and Europe. For example, The Documents of Iriki (1929), the Japanese historical documents of the middle age that Asakawa translated and explained, was highly praised by French historian Marc Bloch. His famous book Feudal Society cited Asakawa’s works in its bibliography. Hu Shih went to the US in 1910 as a scholar on the Boxer Indemnity Scholarship Program. After studying philosophy under the guidance of John Dewey at Columbia University, Hu became professor at Peking University in 1917 where he took the lead in the China’s new culture movement. His essay Wenxue gailiang chuyi (Some Proposals for the Reform in Literature, 1917) triggered the spread of new literature in vernacular Chinese. Zhongguo zhexueshi dagang (Outline of the History of Chinese Philosophy, 1919), based on his Ph.D. dissertation, analyzed the history of Chinese ancient philosophy in a positive and scientific approach, creating a great sensation in the Chinese academia. Asakawa and Hu had thus made remarkable achievements in each academic field. Although Asakawa and Hu were originally very hesitant to be involved in politics, they were ready to take action or express their opinions overseas to protect national interests in cases of national crisis. Their academic careers and political statements have been re-evaluated since the 1980s. It is interesting to note that Asakawa and Hu had accidentally met on the way to their own countries in June 1917. Previous research pays little attention to this fact. But it can be confirmed from their recently discovered diary and letters that Asakawa and Hu formed lasting relationships afterwards. Hu’s views on feudalism were also strongly influenced by Asakawa’s theory. These two closely-tied men were ironically forced to stand in opposition on policies toward the US during the second Sino-Japanese war: Hu Shih served as the Chinese ambassador to the US during 1939–1942, criticizing Japanese invasion to China and calling for the US’s help. During that period, Asakawa appealed to President Roosevelt to send a letter to Emperor Showa to avoid conflicts between US and Japan. This paper clarifies the relationships between Asakawa Kan’ichi and Hu Shih, shedding new light on Japan-China historical relations during the first half of the 20th century.