This article examines the educational philosophy that arises from several focal writings of Rabbi J. B. Soloveitchek. These specific writings, however, do not deal directly with education, and the article illustrates the way that educational doctrine can be shown to arise from philosophical writings as such. On the basis of this research, the article points to possible diversities of interpretation and even confrontations between the conclusions that arise from several texts. In this framework, the authors suggest a new critical interpretation of Rabbi Soloveitchik's thought through the perspective of the philosophy of education. This provides new insight not only to his educational teachings but also into other aspects of his thought.