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 whom he met in Washington, D.C., while working for the Hoover Food Administration. She was the daughter of Herman Fligelman, president and one of the founders of Helena, Montana's New York Dry Goods Store. In 1920 Winestine accepted the offer of the position of general manager of the New York Store and moved to Helena. He managed the store until his retirement in 1958. In Helena, Winestine was active in the Congregation Emanu-El, a Jewish reform congregation. Winestine was also involved with the Montana Institute of the Arts and the Montana Historical Society. He was appointed to the Board of the latter organization by Governor John Bonner in 1949, and served as its president. Norman Winestine died on April 4, 1986.

Belle Fligelman was born in Helena in 1891. She attended Helena schools, graduating from high school in 1909. She then attended the University of Wisconsin in Madison, and during her senior year was elected president of the Women's Self-Governing Student Body. In 1914 she returned to Helena to work as a reporter for the Independent. The following year she was hired to manage and edit the weekly Montana Progressive , published by the state's Progressive Party. It was during this time that she became involved in the successful congressional campaign of Jeannette Rankin. She accompanied Rankin to Washington, D.C., and was employed to write news releases. Throughout her life, Belle Winestine was active in polities supporting movements such as women's suffrage, the Equal Rights Amendment, world peace, etc. In 1932 she unsuccessfully ran for the Montana Senate with her main campaign issue being the creation of a state children's bureau. She was also a prolific writer of short stories, children's stories, plays, and poetry, some of which were published. Belle Winestine died in April 1985.

Norman and Belle Winestine had three children: Minna, Judith, and Henry.