Even while a business executive in the late 1920s and throughout the 1930s, he fostered a keen, growing interest in domestic issues, international issues, and a wide array of other political issues of the day. With the election of Franklin Roosevelt to the presidency in 1932, Bowles saw in the New Deal policies many ideas and concepts that he liked and would promote for decades. Because of the strength and wealth of the United States, Bowles believed that it was essential for America to further develop vigorous, sizable foreign aid programs to a large number of countries. Bowles was a long-time advocate for peace. Because of that deep-rooted sense that peace was vital to survival and happiness of the world's population, Bowles was opposed to the Vietnam War and to the involvement of the United States in Southeast Asia. European reconstruction was vital, he believed, after the massive devastation of World War II. That devastation was due in no small measure to the bombing and other military activities conducted by the US and its Allies over the years of conflict in Europe, in his view. Bowles understood that the Nazi regime of Germany—and others in Axis alliance—needed to be defeated. Yet that meant destruction of buildings, infrastructure, deaths of civilians. Shortly after the war, Bowles saw the hampered abilities of the countries to produce food, clothe their people, provide education, sanitation and health care. Jobs were scarce and opportunities were limited for most people. Yet he was convinced that after the war the United States had a moral obligation to assist with the re-building of affected countries and with meeting the humanitarian needs of the affected people. Civil rights was of paramount importance to Chester Bowles. As a white liberal from the Northeast, he used various tools to foment change that encouraged the independence, freedom and equality for African-Americans and other minorities, supporting changes in the laws advocating for enlightened judicial decisions affecting civil rights. He wrote articles and books that promoted civil rights and agitation for change and improvement, including in a book entitled "What Negroes Can Learn from Gandhi" published in 1958. He advanced these rights by supporting various government programs and private philanthropic initiatives. Bowles had two children (Chester and Barbara) with his first wife, the former Julia Fisk. He was married to Fisk in 1925. They divorced in 1933. Bowles had three children (Cynthia, Sally, and Sam) with his second wife, the former Dorothy Stebbens. He married Stebbens in 1934. Daughter Sally Bowles continued her father's tradition of public service, Chester Jr. is an architect, and Samuel Bowles is a well-known economist and bowler.