Roy Whitcomb, Jr. was born on December 26, 1927 in Cleveland, Ohio. His parents met at Deering High School in Portland, Maine. His father, Roy Sr., served in World War I, and later worked for Goodyear Tire and Rubber in Akron, Ohio and Hally Brothers in Cleveland, Ohio. His mother, Mary Ashton (Rustemeyer) Whitcomb worked for General Electric in Schenectady, New York. Both returned to Maine during the Depression. Roy, Jr. earned his degree in Journalism from Boston University in 1950. He became a police reporter in Fredericksburg, Virginia, then was drafted for two years during the Korean War. He worked for Jim Oliver, and then helped Curtis run for the House in 1964. He was Deputy Secretary of State under Governor Curtis for one day. He served as Director of Democratic Party in New Hampshire, 1965. He was Executive Assistant and Press Secretary under Ken Curtis, during his second term as Governor. He served as the Director for Model Cities in Maine.
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L'Hommedieu, Andrea, "Whitcomb, Roy, Jr. oral history interview" (2000). Edmund S. Muskie Oral History Collection. 407.