He is currently the Edward A. Dickson Emeritus Professor of Economics and Political Science at the University of California, Riverside, and has served as managing editor of the academic journal Latin American Perspectives since its founding in 1974.
His interest in the roots of Latin American poverty shaped his long-term research agenda, beginning with a doctoral dissertation on Spain and continuing with a book on Portugal and the Portuguese colonies in Africa.
This work occurred under the fascist regimes of Francisco Franco in Spain and António de Oliveira Salazar in Portugal, and included a research trip to Angola, where he was arrested by the Portuguese secret police in Luanda and held prisoner and interrogated for ten days.
Chilcote taught in the departments of Economics and Political Science at the University of California, Riverside (UCR) from 1964 to 1994, where he was honored with the Distinguished Teaching Award.
He established a graduate program in comparative political economy, and chaired 40 dissertation committees, serving on an additional 24 for Ph.D. degrees awarded at UCR, UCLA, Rutgers, SUNY, and other universities.
It emphasized scholarship that analyzes national and transnational systems of power and the movements for structural transformation, social justice and human rights in Latin America.
[3][non-primary source needed] A consistent proponent of class analysis, Chilcote critiqued the neo-Marxist and postmodernist theoretical currents that developed as approaches to new social movements, as expressed in his lead article in LAP's 1990 thematic issue on "Post-Marxism, the Left, and Democracy".
He wrote a book on the topic, Latin America: The Struggle with Dependency and Beyond (1974), edited with his student and colleague Joel Edelstein, which was used as a college text and went through eight printings.
His work on Lusophone Africa in the 1960s provided a foundation for an African perspective critical of the Portuguese presence in Angola, Mozambique, Guinea-Bissau, and Cape Verde.
In 2000, Chilcote placed the complete archives of Latin American Perspectives, including all manuscripts submitted, publication decisions, editorial board minutes, annual reports and other working documents, in the UCR Library and recruited additional donations from other scholars.
Since 1974 he has served as a board director of Laguna Greenbelt, which campaigned to preserve 22,000 acres of land in a rapidly urbanizing area of Southern California.
It was previewed at the 2012 LASA Congress but was formally launched in August, followed by his co-curated exhibition of 56 prints from the Osuna archive which opened November 10, 2012, at the California Museum of Photography in Riverside.