Dr. Craig Winkelman - '87

As the superintendent of Barrington School District 220, Dr. Craig Winkelman’s most important objective is to be student-centered in the decisions made for the district, most importantly giving students interesting and unique experiences inside and outside the classroom. One of the most progressive ideas he has implemented is encouraging students to be more active in civic affairs. “We have encouraged students of all grades to attend and present at our school board meetings,” said Winkelman. “It’s a great way for them to inform the board and the community about their accomplishments while practicing their presentation skills,” he adds. 

It was Winkelman’s great student experience at District 21 that propelled him into a career in education. Teachers at the school he attended, especially Miss Sandford, his third and fourth grade teacher at Twain Elementary School, made a connection with him. Other influences included Mr. Cook, his sixth grade teacher at Mark Twain Elementary School, who was a wonderful role model. “He was my first male teacher and he made a great impression on me,” said Winkelman. “I also had a great relationship with my wrestling coaches, Mr. Klatecki  and Mr. Perlow, at Holmes Middle School. They all really cared about us,” he added. And it’s that kind of care and attention that drives students to give back in the same way and become teachers themselves. 

After attending Wheeling High School, Winkelman earned his associate degree from Harper College. He then earned a bachelor’s degree in special education from Illinois State University, a master’s degree in educational administration from Northern Illinois University, and a doctorate in educational leadership from National Louis University. 

Starting at the district in 1996 as a special education teacher at Barrington High School, Winkelman taught biology, physical science, and Adventure PhysEd classes. “I’d take the students kayaking, rock climbing and to high ropes courses, among other activities, to promote team building, confidence, and leadership skills. From there, he worked as an assistant principal at Barrington Middle School – Station Campus, then as a principal at Sundling Junior High School in Palatine (Community Consolidated School District 15). In 2006, he returned to Barrington’s Station Campus as principal and eventually was promoted to the superintendent in 2023, the only person who has advanced from teacher to superintendent in the district, a unique accomplishment. 

Outside of work, Winkelman enjoys outdoor watersports, including wakeboarding, waterskiing, and muskie fishing. His wife, Amy, works at Barrington High School as a prevention and wellness counselor. Their two daughters are in college, studying nursing.  

Winkelman’s education at District 21 inspired him to become a teacher and give back to the community. His positions in education have allowed him to shape future generations. We are honored to call him an alumnus. To learn more about Dr. Winkelman, click here.