Sol Stern was born in Ramat Gan, Israel (then in Mandatory Palestine) in 1935. He was raised in the Bronx from infancy, and attended the City College of New York, the University of Iowa, and Berkeley.
Stern began his career with the radical magazine Ramparts. In 1967, he contributed the article " A Short Account of International Student Politics and the Cold War with Particular Reference to the NSA, CIA, etc." to the magazine. It included the allegation that the Central Intelligence Agency (CIA) had supported the National Student Association, ties which later were confirmed by the organization itself. The CIA funded overseas' projects to the tune of $3.3 million, and recruited NSA staff members for intelligence work. In 1968, Stern signed the "Writers and Editors War Tax Protest" pledge, vowing to refuse tax payments in protest against the Vietnam War.
His departure from radicalism came after New Left attacks on Israel. He also collaborated with Ronald Radosh on a research project into the evidence against Julius and Ethel Rosenberg. Originally intending to prove their innocence, Stern and Radosh came to believe that the Rosenbergs had been guilty of spying for the Soviet Union. New York Times described him as a "cantankerous provocateur against liberal education policies, criticizing reading curriculums that de-emphasize phonics as well as public schools that focus on social justice." Stern has written critiques of Bill Ayers' career as an education reformer for City Journal and elsewhere.