Life has a funny way of coming full circle. A simple twist of fate, in this case, a bum knee that had its initial stirrings on KO’s soccer fields set Andy Krugman ’86 on the path of teaching at the school for the past 27 years. “Blowing out my knee was one of the better blessings I’ve had,” he said. While he was rehabbing at home in West Hartford after college, he learned of the Warren Baird Teaching Fellowship at KO and applied for the position. Although the legal field might have been one more member strong if Krugman pursued that career path, countless KO students would have been denied his warmth and humanity and his self-described “weak attempts at humor.”

KO is built on relationships and connections, and Krugman embraces all of them. “Every day I have between 200 and 400 interactions with great kids and supportive families,” he said. “That sure beats a cubicle.” He acknowledges the satisfaction he receives when a student who has his or her ups and downs shows continued growth. He sees that aspect in himself as a student who gratefully acknowledges that he learned how to be a student at KO. “When I initially started high school, I saw myself as an athlete, but when I graduated from KO, I left as a student-athlete,” he said. “In college, I was very well prepared.”

Krugman is quick to tell you all the teachers and coaches at KO who impacted his life by encouraging him to try new things. There’s Chuck Glassmire, who pushed him into tennis and his advisor Dave Emory ’75, a Middlebury alum who, as Krugman’s soccer coach, inspired Krugman’s own path to Middlebury. Krugman believes that coaching is teaching, and he views it as an art more than a science. “I think students learn more about themselves from this than in other areas of the school,” he said. “It’s competitive, fun and hard.” He regards the time spent with the players on the bus rides to and from games as time very well spent. Those small conversations, such as talking to a student about the adaptation of a book to film, are both meaningful and fascinating to Krugman.

“This place is like home to me,” he said. “The fact that I became a teacher is a tribute to the power of KO education.”

Andy Krugman ’86
Middle School History Chair, Varsity Boys’ Tennis Coach
Middlebury College B.A.
Trinity College M.A.