Rafal Olechowski, 37, has been teaching for a decade. In keeping with the Milken Foundation's tradition, he was caught by surprise when presented with the award during a school assembly on Thursday.
Mr. Olechowski said he was thrilled. When asked what he does that's so special, he said he tries to connect his 10th graders to literature through 19th-century romantic poets, specifically sonnets.
"If you look at Keats, someone like that, or Byron or Shelley, they appeal to teenagers," he said. "They have this free spirit. I mean they're the hippies of the 19th century!"
Mr. Olechowski also teaches a colloquium-style course for 12th graders at Queens College, in which students read a classic of Western literature each week "from the Bible to Virginia Woolf" and get college credit.
"There almost isn't any real teaching; it's more like a Socratic seminar," he said.
Mr. Olechowski, who was born in Poland, started working as a substitute teacher in New York City schools while working on a graduate degree in medieval studies at Fordham University. He said he fell in love with the profession and decided not to pursue his doctorate.
He said the Milken award comes at a good time because he and his wife are expecting their first child this spring.
Almost 40 teachers around the country received the awards in recent days, all during surprise assemblies at their schools. Mr. Olechowski was the only one from New York schools.