This chapter describes the early years of Rabbi Jehiel Jacob Weinberg's (1884–1966) life amid the backdrop of the final decades of the nineteenth century. Within this milieu, the Jews in Russia, Poland, and Lithuania were coming to grips with a number of new movements and philosophies. Although the apostles of Jewish enlightenment (Haskalah), through their propagation of new ideals, had some influence in bringing about a modernization and acculturation, there were other important factors which were independent of Haskalah, although often indirectly nourished by it. It was into this east European Jewish society in transition that Weinberg was born in 1884, in Ciechanowiec, Poland. From there, the chapter describes Weinberg's early childhood and schooling. The latter in particular occurred during a controversy over the musar movement, founded upon the ideologies of Rabbi Israel Salanter.