Norman Winestine was born February 15, 1895, in Wassaic, New York, and was raised in Waterbury, Connecticut. He received a bachelor's degree from Yale University and did post-graduate work in medieval history at Columbia University and at the newly established Dropsie College for Hebrew and Cognate Learning in Philadelphia. At Dropsie, Winestine studied Semitic language and Judaism. On April 18, 1918, Winestine married Belle Fligelman, daughter of Herman Fligelman, president and one of the founders of Helena, Montana's New York Dry Goods Company. In 1920, while living in Paris, France, Winestine accepted the offer of the position of general manager of the New York Dry Goods Company, popularly known as the New York Store. The store had been founded in 1882, under the name of H. Loble & Co., by Herman Fligelman and Henry Loble, both Romanian immigrants, and Robert Heller, an Austrian. The store was formally incorporated as the New York Dry Goods Company in 1890. When Winestine arrived in Helena in 1920, only Herman Fligelman of the original owners remained, Henry Loble having died in 1913 and Robert Heller having retired in 1920. The New York Store was destroyed by fire in 1928, but under Winestine's direction was rebuilt and renamed Fligelman's. Four years later, in 1932, founder Herman Fligelman died. Fligelman's was sold in 1958 to the J.M. McDonald Company. After moving to Helena, Winestine joined Congregation Emanu-El, a Jewish reform congregation. It had been reformed in August 1889 and a temple building completed in 1890. In April 1890 the congregation hired its first rabbi, Dr. Samuel Shulman of New York. Starting in 1925, Norman Winestine conducted the services on High Holy Days. Due to a decline in membership, the congregation was no longer able to support the maintenance of a temple, and decided to sell the building to the Montana Relief Commission in 1935. Winestine continued to conduct services for the few remaining members of the congregation, until after World War II.