John Dewey was an American philosopher, psychologist, and educational reformer whose ideas have been influential on education in Japan and China. Hu Shih made a notable contribution to this influence through his introduction of John Dewey to modern China (the period of the Republic of China on the mainland, 1912–1949). Hu studied philosophy at the Teachers College at Columbia University from 1915 to 1917, during which time he was greatly influenced by his professor, Dewey. Hu was a famous Chinese thinker, philosopher, essayist, and diplomat who was influential in the May Fourth Movement and one of the leaders of China’s New Culture Movement. In this paper, I clarify the relationship between the thought of Hu and Dewey by referencing Hu’s career and achievements. Specifically, this paper aims to clarify Hu’s ideological characteristics during various periods in his life. Through this process of exploration, we see how, in the great tide of times, Hu, a traditional intellectual, accepted and renewed Dewey’s ideas. Specifically, I consider, in detail, Hu’s ideas at each stage of his career (before, during, and after studying abroad) and the connection between his ideas, his educational practices, and Dewey’s thought.