In 1869, a deeply religious Jerusalemite named Yosef Rivlin made a radical decision: to become the first Jew to permanently live outside the Old City's ancient walls. Born in 1837 to a prominent rabbinical family, Rivlin defied both community leaders and relatives who viewed leaving the walled confines as dangerous and sacrilegious. Drawing from historical documents, correspondence, and contemporary accounts, this biographical analysis reveals how Rivlin, inspired by the mystical teachings of Rabbi Elijah Gaon of Vilna on redemption through settlement, orchestrated a dramatic expansion of Jewish Jerusalem. He assembled a seven-member building cooperative that pioneered innovative financing mechanisms to purchase land and construct homes in what became known as Nahlat Shiva. Despite facing physical threats, public ridicule, and personal tragedies, Rivlin's persistence led to the establishment of multiple settlements including Mea Shearim and Even Yisrael. His achievements fundamentally transformed Jerusalem's demographic landscape, creating the foundation for modern Jewish settlement patterns beyond the historic walls and establishing him as a crucial figure in pre-Zionist Palestinian Jewish history.