Freedman was born in Rochester, Minnesota, where his father finished his residency at Mayo Clinic. The family relocated to Denver and Freedman graduated from George Washington High School in 1968. He went on to study at Columbia College and received his A.B. in literature in 1972 and earned a fellowship that allowed him to travel through Central and South America.
He began his journalism career as a reporter for the Associated Press in Sao Paolo and Rio de Janeiro during 1974-75. He then became a freelance writer and lived in Washington D.C., Spain, Portugal, and San Francisco until he was hired by The Tribune in 1981.
During his tenure at the newspaper, he was a finalist for the Pulitzer Prize for Editorial Writing in 1983 and 1984, and won the award in 1987 for writing about immigration across the U.S.-Mexico border. His series of editorials that lasted for six years, was instrumental in the passing of the Immigration Reform and Control Act of 1986, the first major immigration reform act in 34 years and granted legalization to over two million people.
- From Cradle to Grave: The Human Face of Poverty in America, Atheneum, 1993
- The Last Brazil of Benjamin East: A Novel, Bright Light Press, 2015
- Solito, Solita: Crossing Borders with Youth Refugees from Central America, Haymarket Books, 2019
- Wall of Fame: One Teacher, One Class, and the Power to Save Schools and Transform Lives, AVID Center, 2020
- Fischer, Heinz (2012-02-14). Political Editorial 1916-1988: From War-related Conflicts to Metropolitan Disputes. Walter de Gruyter. ISBN 978-3-11-097229-0.
- "Jonathan Freedman of The Tribune, San Diego, CA". The Pulitzer Prizes. Retrieved June 20, 2020.
- "Pulitzer Prize-winning journalist. Novelist. Social activist". Post Bulletin. Retrieved 2020-06-20.
- "Bookshelf". Columbia College Today. Fall 2015. Retrieved June 20, 2020.
- Hamlin, Abby (2019-04-11). "1987 Pulitzer Prize-winner wrote about immigration. Here's what he thinks now". San Diego Union-Tribune. Retrieved 2020-06-20.
- "'The law did not solve all the problems of immigration'". The Pulitzer Prizes. Retrieved June 20, 2020.