“I’m a liberal whose children were mugged by the public schools,” Mr. Stern said.

His history with the city’s schools goes back to his childhood. Just before World War II, Mr. Stern immigrated with his parents from what was then Palestine. The family settled near Fordham Road in the Bronx, where Mr. Stern attended Public School 6 until eighth grade. He went on to Stuyvesant High School and City College, and then started but did not finish a doctorate in political science at the University of California, Berkeley.

Image Ive always been in a dissenting position. SOL STERN Senior fellow at the Manhattan Institute Credit... Chester Higgins Jr./The New York Times

At Berkeley, he became entranced, he said, by the left-wing student movement and dropped out to write for the radical magazine Ramparts, gaining national attention. One of his most famous articles included assertions that the Central Intelligence Agency had infiltrated the National Student Association, a group of student governments, as part of its Cold War strategy.

Like other neoconservatives, however, Mr. Stern began splitting with the left over the Middle East, reacting to what he saw as an anti-Israel philosophy. In the early 1970s, he became curious about his family’s history and returned to the renamed Israel for the first time since he was a toddler. On that trip, Mr. Stern found himself “falling in love with the country,” he said, and he later met his wife in Jerusalem.

They moved back to New York City in the mid-70s, where Mr. Stern continued writing for several magazines and newspapers. In the ’80s, he met the City Council president, Andrew Stein, through a mutual acquaintance and became his chief of staff.

Although he was involved in several political campaigns with Mr. Stein, who was a Democrat, Mr. Stern said he was never involved in the city’s Democratic political circles. And while his political views have gradually changed to what he calls “somewhat traditionally conservative,” Mr. Stern has remained a registered Democrat, partly out of “inertia” and the desire to have a vote in the primaries. (He voted for Senator Hillary Rodham Clinton last week and says he will probably vote for Senator John McCain in November.)

Mr. Stern prefers personal anecdotes to describe his political evolution. While he was working for Mr. Stein, he was often able to take his children to school near their home on the Upper West Side. One morning, he spotted a man he assumed was homeless wandering through the schoolyard.

“He looked terrible  battered clothes, a worn shopping bag  just terrible,” he said, grimacing at the memory.