Stern began his career with the radical magazine Ramparts to which, 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."
It included the allegation that the Central Intelligence Agency (CIA) had supported the National Student Association, ties that later were confirmed by the organization itself.
The CIA funded overseas projects to the tune of $3.3 million, and it recruited NSA staff members for intelligence work.
In 2008, The 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.
[8][9] In 2020, Stern publicly broke with City Journal, arguing the magazine had lost its independent outlook in the Trump era.