Caroline (Duby) Glassman was born on September 13, 1922 in Baker, Oregon, and grew up on a cattle ranch outside of Baker. Her father, Charles, was a Democrat, and her mother, Caroline, was a Republican. After graduating from a one room school house, she went to Eastern Oregon University in La Grande. At the age of 18 she began law school at a university in Salem, Oregon. After graduating, she worked as a title insurance attorney for about a year and then traveled around the country taking positions such as legal secretary, medical secretary, and magistrate for the court. She took the bar exam in San Francisco and practiced law there for a while. In 1962, she moved with her husband, Harry, and their son, Max, to Portland, Maine and she continued to practice law there. In 1967, she got involved in the Model Cities Program, beginning with writing the application. Her husband received a grant to teach in Yugoslavia for year, which caused her to step down from the program, but health concerns prevailed and instead, she started her own practice. At the time of this interview she was an active member of the Maine Supreme Judicial Court.
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Beam, Greg, "Glassman, Caroline oral history interview" (2000). Edmund S. Muskie Oral History Collection. 144.