Oregon City High School Math Teacher Jennifer Crutcher Named Clackamas Regional Teacher Of The Year (Photo) - 09/22/26
Crutcher also selected as one of four finalists for 2026–27 Oregon Teacher of the Year
OREGON CITY, Ore. — Jennifer Crutcher, a math teacher at Oregon City High School, has been named the 2026–27 Clackamas Regional Teacher of the Year and selected as one of four finalists for Oregon Teacher of the Year.
Crutcher learned of the honors during a surprise celebration at Oregon City High School on Monday, Sept. 21. Students and staff were joined by Oregon City School District Superintendent Dayle Spitzer, representatives from Clackamas Education Service District and other special guests to recognize Crutcher and celebrate her impact as an educator.
“Jennifer Crutcher represents the very best of public education — a math teacher who sees the strengths and potential in each student and creates the conditions for them to grow with confidence,” said Clackamas ESD Superintendent Larry Didway. “Her ability to make rigorous math learning relevant, welcoming, and connected to the world beyond the classroom is a powerful example of what great teaching looks like. We are proud to recognize Jennifer as the Clackamas Regional Teacher of the Year and grateful for the lasting difference she makes for students, families, and her school community.”
Crutcher was nominated by a former student who described her classroom as an “incredibly safe and inclusive space” and praised her ability to explain mathematical concepts in different ways to strengthen student understanding.
“Working with Mrs. Crutcher, I felt more heard than I ever had,” the student wrote. “She took the time to find ways to help me succeed in her classes. With her support, I took more higher-level math classes, including AP Calculus, than I ever thought I would, or could, and passed them with solid grades.”
Crutcher said her teaching philosophy centers on helping students connect classroom learning with the world around them.
“My teaching philosophy is centered on the belief that to truly engage students, we must dissolve the walls of the classroom and weave application and the community into the curriculum,” Crutcher wrote in her application. “By inviting the community into my classroom and leading my students out into the world, I am not just teaching them how to solve problems; I am showing them where they belong in the solution.”
Crutcher was selected from a strong field of educators nominated across Clackamas County. The other finalists for the 2026–27 Clackamas Regional Teacher of the Year were:
North Clackamas School District
- Ellie Cook, Mount Scott Elementary School
- Emily Olson, Bilquist Elementary School
- Jessica Augden, Alder Creek Middle School
- Robin Troche, Milwaukie High School
- Shelly Waller, Beatrice Morrow Cannady Elementary School
- Todd Koebke, Sabin-Schellenberg Center
- Tracy Dato, Adrienne C. Nelson High School
Oregon City School District
- Megan McCormick, Gardiner Middle School
Lake Oswego School District
- Jennifer Jillions, Lakeridge High School
Oregon Trail School District
- Jeremy Magee, Sandy High School
School affiliations reflect employment during the 2025–26 school year.
The Oregon Teacher of the Year Program recognizes outstanding licensed public school educators from across the state. Clackamas ESD coordinates the regional nomination and selection process for Clackamas County.
Crutcher is one of 11 Regional Teachers of the Year statewide and now advances as one of four finalists for the 2026–27 Oregon Teacher of the Year honor. The program is led by the Oregon Department of Education in partnership with the Oregon Lottery. Each Regional Teacher of the Year receives a $1,000 award.
The 2026–27 Oregon Teacher of the Year will be announced later this fall.