Hillman first ventured into politics as a young woman, campaigning for Republican presidential candidate
Dwight D. Eisenhower because she saw him as a war hero. She had already registered as a Republican—both because of family tradition and the party’s support for women, including the Equal Rights Amendment (ERA) (which the party supported in its platform until 1980). After Ike’s successful campaigns, Hillman remained involved in the Republican party during the 1960s as a volunteer at the local level. Her work in Pittsburgh and Allegheny County caused her to see how few African American men or women were involved in her party, so she arranged to meet with the county party chairman to raise the issue. He suggested that she meet Wendell Freeland, an African American lawyer and Tuskegee Airman, to team-up to recruit more volunteers and candidates from the city’s African American community. Hillman and Freeland did this, going on to organize neighborhoods across the City of Pittsburgh and becoming lifelong friends through political and civic work that spanned decades. Their work took Hillman into neighborhoods of Pittsburgh and the county she had never been. It was during this period that she developed her connections with African American leaders as well as a sense of outrage about the civil rights being denied to Black Americans. She volunteered for the board of directors of several traditionally African American organizations, including the Hill House Association, and began to speak publicly for civil rights. Hillman and Freeland were able to reach African American voters in ways that the party had not before
Never a Spectator and they organized large-scale events, including a 17,000-person rally for
William Scranton when he ran for governor; Scranton was elected in 1962. Because of Scranton’s moderate views and strong support of Civil Rights legislation, Hillman backed his candidacy during the 1964 Republican presidential primary in San Francisco (after having worked actively for
Nelson Rockefeller, who withdrew from the race). She witnessed the poor treatment of African American Republican delegates by some of those who opposed Scranton. Scranton ultimately lost the nomination to Senator Barry Goldwater, who would go on to be defeated in the general election by Lyndon Johnson. Hillman worked to elect Senator
Hugh Scott, who had led the Republican National Committee and would rise to the position of Senate Minority Leader. With Scott’s encouragement, she ran for the position of chair of the Allegheny County Republican Party and was elected to the job in 1967—the first woman elected to head the party of an urban area. It was during her time as party chair that she worked to field winning candidates and develop connections with her counterparts across the state of Pennsylvania, including the members of the Republican State Committee of Pennsylvania. During and after her tenure as party chair, Hillman worked to advance moderate candidates who supported civil rights and women’s rights—urging them to run, helping them to organize their campaigns (often staffing them, as a volunteer), and connecting them with the leaders of organized labor and other influential groups. She and her family made extensive contributions to campaigns as well, eventually establishing a political action committee to support moderate candidates. She was also known as a supporter of abortion rights. She was honored as "Woman of the Year" for 1982 by Vectors/Pittsburgh. In 2002, she was named to the
PoliticsPA list of "Sy Snyder's Power 50." In 2003, she was named to the
PoliticsPA "Power 50" list. She was named to the
PoliticsPA list of "Pennsylvania's Most Politically Powerful Women." In 2010,
Politics Magazine named her one of the most influential Republicans in Pennsylvania, calling her the "grand dame of big tent Republican politics." ==Philanthropy==