John Dewey was an American philosopher, psychologist, and educational reformer whose ideas have influenced education in Japan and China. Tanimoto Tomeri played a notable role in paving the way for this influence by introducing John Dewey to modern Japan (the Taisho era (1912-1926)). Tanimoto Tomeri (1867-1946) was an educational reformer during the Meiji era until the early Showa era and is valued as a leader of the Taisho-era Free Education Movement. He is believed to have contributed greatly to the development of education in modern Japan. In this paper, I will elucidate the connection between the thoughts of Tanimoto and those of Dewey by referencing Tanimoto’s career and achievements. Specifically, I will highlight Tanimoto’s ideological characteristics during various periods of his life. The study will reveal how, in the great tide of times, Tanimoto Tomeri accepted and renewed Dewey’s ideas. I will examine in detail Tanimoto’s ideas at each stage of his career and the connection between his ideas, his educational practices, and Dewey’s thought.