Midtown Surprise: Teacher Wins $25G FLAG Award for Teaching Excellence

A black box theater in Repertory Company High School for Theatre Arts was quietly filling with students and faculty holding signs and confetti, eagerly awaiting the entrance of one particular teacher. While everyone gathered, Ian Weissman, a social studies teacher at Repertory, was on a Zoom call with a colleague that was meant to prevent him from learning of the surprise award and ceremonial preparations. Once Weissman entered the theater, he was greeted by cheering colleagues and students who were ecstatically celebrating their teacher’s--and their school’s--win.

This year, the Manhattan recipient of the FLAG Award for Teaching Excellence is Weissman, who combines history, civics, performance, and technology within his classes to create exciting projects and learning experiences for students.

He gets a personal check for $25,000 as well as a $10,000 prize to be used on a school project of his choosing. As part of the High School’s AI Fellows Initiative and the Modern Classrooms Project, he is particularly interested in the incorporation of AI tools to create historical simulations and interactive lessons.

Weissman is the teacher leader of Repertory’s Equity Team and Exchange Manager for the American Exchange Project, where he helps students participate in cross-country exchange programs. He also advises the Guitar Club and the Jewish Student Group of Repertory.

Repertory Company High School for Theatre Arts is regarded as “hidden gem” theatre school, providing students with a holistic education in history and current events which accompanies their versatile arts classes. Located inside the historic Town Hall Theater, Repertory students take classes ranging from dance, acting, music theory, and theater production, complemented by traditional academic coursework and Advanced Placement classes.

Amanda and Glenn Fuhrman co-founded the FLAG Award for Teaching Excellence in 2019 to honor teachers who are “really going above and beyond the call of duty to do something unique and something special,” said Glenn Fuhrman in a video on the Flag Award website.

The award honors one outstanding high school teacher per borough, plus one 3K-to-5th grade teacher. Six awardees win $25,000 each along with $10,000 for their schools; 11 finalists win $10,000 each, plus $5,000 for their schools.

Winners are selected by an independent jury composed of leaders in education, the arts, and the social sciences. The 2026 jury includes Emily Chandler, winner of the 2025 FLAG Award for Teaching Excellence Brooklyn Grand Prize; Mark Dunetz, President of New Visions for Public Schools; Pam Haas, Executive Director of the NY region of Facing History & Ourselves; Betty A. Rosa, Commissioner of Education and President of the University of the State of New York; and Shamilia McBean Tocruray, Director of Education at the Brooklyn Museum.

Weissman is one of six teachers citywide to be selected for the award. “These remarkable educators are helping New York City students imagine new possibilities for their futures in fields ranging from journalism to ethical AI and environmental justice,” said Amanda Fuhrman.

With his grant funding, Weissman would like to launch “History in Your Hands” using 3D printing and laser-cutting technology to help students design and fabricate historically-inspired artifacts connected to their own research projects. His hope is that this project will allow students to “actually manipulate and hold little pieces of history. I just love physical objects and the connections to history, but obviously there are things in museums that we can’t hold so I thought it would be really cool to create realistic replicas of historical artifacts for students to work with.”

When asked about what makes him most proud as a teacher, Weissman shared, “In teaching, there’s victories every moment of the day when a student gets something or when a student finds themselves in the work that they’re doing, or changes the way that they see the world. Those are all the huge things that motivate me.”

His goals for the future? “We have the Regents on Wednesday so that’s the first goal! More seriously, though, to continue teaching. This is my passion, there’s nothing else I would rather be doing with my life and my career. And to just continue being the best teacher that I can.”

Weissman’s impact as a teacher was evident in his students’ ecstatic reaction to his award. Little could be heard in the school hallways besides “Congratulations, Mr. W!” and “We love you!”