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Milwaukee City Wire

Wednesday, September 10, 2025

Reagan High School teacher receives Yale Educator Award

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Dr. Keith P. Posley Superintendent at Milwaukee Public Schools | Official website

Dr. Keith P. Posley Superintendent at Milwaukee Public Schools | Official website

Max Smith, a graduate of Reagan High School, recently nominated his former teacher Kurt Dillman for the 2024 Yale Educator Award. The award is part of the Yale Educator Recognition Program, which honors educators who inspire and support their students to achieve excellence. Dillman, a social studies teacher at Reagan, is one of 75 educators from 24 countries to receive this recognition in 2024.

Dillman's journey into education began later in life. After initially dropping out of college at 19, he returned to higher education in his forties. He completed a bachelor's program at the University of Wisconsin-Milwaukee (UWM) and a master's program at Alverno College. Reflecting on his path, Dillman said, "I was very fortunate to land at Reagan as a student teacher in special education and social studies."

Max Smith praised Dillman's ability to see beyond academics in his nomination letter: “Mr. Dillman sees things in his students that they don’t see.” When asked about his approach to teaching, Dillman emphasized individual attention: "I tried to find one extracurricular activity each student is involved in—it gives me something to talk to them about."

Dillman also teaches Theory of Knowledge (TOK), the capstone course for the International Baccalaureate Diploma Programme. He explained its significance by saying, "The International Baccalaureate curriculum expects you to apply everything you learn to real-life situations."

In discussing successful teaching strategies, Dillman highlighted creating an inclusive classroom environment: "Classes are most successful when I talk the least." He added that high expectations are key: "High expectations correlate with academic success."

Reflecting on his career choice as an educator, Dillman shared a meaningful moment with a former student who acknowledged him for inspiring her master’s research. He stated, "Sometimes, I think I learn more from the students than they do from me."

Dillman's experience highlights the impact of lifelong learning and diverse perspectives in education. His dedication continues to influence students positively at Reagan High School.

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