The influence of his parents and grandparents left him deeply aware of what it meant to be working class.
As a youth, he often explored working-class neighborhoods and felt a deep affinity for other similarly situated people.
In 1984, Freeman obtained a position as a senior research scholar at the CUNY Graduate Center, where he worked at the American Social History Project as a writer on the second volume of the project's two-volume textbook, Who Built America: Working People and the Nation's Economy, Politics, Culture and Society.
Freeman's 2000 book, Working-Class New York: Life and Labor Since World War II, also won positive reviews.
Freeman intended that the book correct histories of New York City which focused on wealthy elites, elected leaders and organizations.
Throughout the first half of the book, Freeman argues that everyday workers were at least as influential as these other groups in making New York City into a progressive bastion and world economic and cultural center.
In 2012, Freeman released American Empire, 1945-2000: The Rise of a Global Power, The Democratic Revolution at Home.