In 2007, he made the transition from teaching in college to the high school environment, and he is currently in his 11th year teaching Latin (and sometimes Greek) at Westwood High School in Westwood, MA.

He is the past-President of the Classical Association of Massachusetts (CAM), the Coordinator of Educational Programs for the Classical Association of New England (CANE), Advocacy Coordinator for the Massachusetts Foreign Language Association (MaFLA), and the Massachusetts representative to the National Council of State Supervisors of Foreign Languages (NCSSFL). He has won numerous teaching awards at both the high school and college levels for his unorthodox approaches to teaching language, history, & culture, and he is regarded as a national language advocate. He was the ACTFL 2016 National Language Teacher of the Year.