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Josh Dingeldein and dignitaries when he won the Milken Educator Award

2015 Alumnus Wins Milken Educator Award

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Josh Dingeldein teaching English class.

Josh Dingeldein ‘15 thought the surprise school assembly at Plymouth High School was because of a visit from Indiana Secretary of Education Dr. Katie Jenner. As Secretary Jenner began to talk about a teacher from the school winning the prestigious Milken Educator Award, Dingeldein started to get excited - but not for himself. 

“As I listened, I just thought how amazing it is that the Milken Family Foundation exists,” he said. “I thought it was so legit for educators to be recognized. Teaching comes with its own rewards - you get to see the difference and the impact of what you're doing. For this organization to put it on blast like that is just amazing.”

And then, to his amazement, Dingeldein heard his name being announced as the winner. The award comes with a $25,000 prize. 

Known as the “Oscar of education awards,” the Milken Educator Award honors up to 75 teachers across the country each year. Dingeldein is the first teacher from Plymouth High School to win the award and is just one of two teachers in Indiana to be awarded this year. 

“Talented teachers like Josh Dingeldein not only promote rigor and critical thinking, but also develop in their students a true love of learning,” said Milken Educator Awards Senior Vice President Dr. Jane Foley, who presented the award with Secretary Jenner.

“Josh sees a clear path to success for each student and guides them every step of the way. He brings that same enthusiasm to collaborating with colleagues, leading professional development, and innovative approaches to take learning to new heights.”

The award specifically recognizes new to mid-career K-12 teachers who demonstrate excellence and leadership in the profession. 

Dingeldein teaches 9th and 11th grade English and language arts, as well as AP classes. He’s been at Plymouth High School for five years. Prior to that, he and his wife, Jackie, lived in Denver, Colorado, where he taught for four years. They moved to Plymouth, a small town in northern Indiana, to be closer to their families in Indiana and Ohio. Together, they are the parents of 1-year-old Benaiah. 

Dingeldein recognizes that any positive impact with his teaching is a result of God's help. He also credits the professors in the Education Department, as well as his football coaches at Taylor, with preparing him to work hard, teach well, and love his students.  

“I’m a recipient of people who love the Lord and invested in my life,” he said. “When I first visited Taylor as a high school student, I knew this was where the Lord wanted me to go to school. I knew that these were the people I wanted to surround myself with.” 

Dingeldein uses innovative instructional methods that help keep students engaged in the tasks at hand and committed to their own growth as learners. He even implemented tools from ChatGPT, choosing to view AI as an opportunity rather than threat. Working with other teachers at the school, he created ChatGPT prompts that helped students receive real-time feedback they could use to improve their writing. 

Most importantly, his goal is to communicate that each student he interacts with in class has worth, dignity, and incredible potential. 

“Education provides students with an opportunity for hope to pursue the role that he or she is after. I get excited about every new day because every day brings opportunities for hope, and to give hope to students.” 

Photos courtesy of the Milken Family Foundation.