The Devil & Saint Ann's

Stanley Bosworth, the mad genius behind one of New York’s legendary schools, is not going gently into that good night.

“Have you ever seen the movie Gone With the Wind?” Stanley Bosworth asks, fixing me in his gaze. “ ‘Frankly, my dear, I don’t give a damn.’ ” He is referring to the Wall Street Journal’s ranking of the school he founded, Saint Ann’s, as No. 1 in the country. Bosworth is in his lair, his huge headmaster’s office, decorated with the work of his students—life drawings of nudes, a still from a film by Lola Schnabel—and photos of his various children and stepchildren and ex-wives. 

Despite his Dixie nonchalance, Bosworth just happens to have that particular issue of the Journal, now a week old, lying open on the table. “I love being No. 1 in anything,” he declares. “But whether it’s exciting in that other sense of I’m in the money now or I’m the best, it doesn’t mean best. What’s best about us, I hope, is that we teach them the ‘forest of symbols,’ to borrow deliberately from a poem called ‘Correspondences,’ by Baudelaire.” 

Bosworth has been headmaster at Saint Ann’s since its inception in 1965. Certain aspects of his vision have been revised over the years: Attending class is no longer optional for high-school students, and the student smoking lounge—which used to vote in a king and queen annually, each dubbed with a cigarette—is no more. But it’s still a very unusual place, an artsy Hogwarts in Brooklyn Heights, where many things—special things!—are possible and few are forbidden. 

Bosworth is 76 years old and very tall, and he is very, very sure of himself and his school and his role in it. “Hey, baby,” he says, “when I run Saint Ann’s, there’s one person. Do you know any French? I’ll do it for you in English: The French say a single person is missing, and there’s no one in the world.” 

When you talk to Saint Ann’s people—faculty, alumni, parents—about Stanley, which is what they all call him, they tend to use the language of awe. (The word his assistant Elena Gershoni uses to describe his reputation is mystic.) But on May 3, Stanley must attend his own farewell party, his “bar mitzvah,” as he’s taken to calling it. After a 39-year reign, he’s being put out to pasture by his board, to be replaced by Dr. Lawrence S. Weiss from Horace Mann, who’s 54 years old. Soon, Saint Ann’s will have to see what it is without its creator. And vice versa...