Oregon City High School is proud to celebrate mathematics teacher Jennifer Crutcher, who has been named the Clackamas Regional Teacher of the Year and selected as one of four statewide finalists for the 2026–27 Oregon Teacher of the Year honor.
Crutcher was honored with the announcement during a celebration at Oregon City High School on Monday, Sept. 21. The recognition is part of the statewide Oregon Teacher of the Year Program, led by the Oregon Department of Education and supported through its partnership with the Oregon Lottery. The regional selection process is facilitated locally by Clackamas Education Service District.
“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. 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,” said Larry Didway, Clackamas ESD Superintendent.
Crutcher was nominated by a former student, who described her classroom as an “incredibly safe and inclusive space” and praised her ability to teach mathematical concepts in multiple ways to deepen student understanding.
“Working with Mrs. Crutcher, I felt more heard than I ever had,” the student wrote in the nomination. “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.”
In her nomination materials, Crutcher shared that her teaching philosophy centers on engaging students by connecting learning to the world beyond the classroom.
“To truly engage students, we must dissolve the walls of the classroom and weave application and the community into the curriculum,” Crutcher said. “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.”
Statewide Recognition
Crutcher is one of 17 educators across Oregon selected as a 2026–27 Regional Teacher of the Year. Regional winners are nominated by students, colleagues, administrators, friends or family members, then participate in a local application and selection process coordinated by Oregon’s 19 education service districts.
According to the Oregon Department of Education, candidates are evaluated on leadership, instructional expertise, commitment to equity, community involvement, understanding of educational issues, vision and professional development. Each regional winner receives a $1,000 award through the Oregon Department of Education’s partnership with the Oregon Lottery and advances as a semifinalist for the statewide Oregon Teacher of the Year award.
The 2026–27 Oregon Teacher of the Year will be announced later this fall. The statewide honoree will receive a $10,000 cash award, with an additional $5,000 awarded to the recipient’s school, thanks to the partnership between the Oregon Department of Education and the Oregon Lottery.
Celebrating Excellence in Education
The Oregon Teacher of the Year Program recognizes licensed public-school educators in prekindergarten through grade 12 who demonstrate exceptional dedication, knowledge, skill and leadership on behalf of students.
“We are so proud of this year’s Regional Teachers of the Year who consistently demonstrate hard work, build strong relationships, empower their students, and create classroom environments that lead to student success,” Oregon Department of Education Director Dr. Charlene Williams said. “As mentors, advocates, and community leaders, they show us all that the best is on display in schools large and small, rural and urban, from the first years of schooling to the final preparations for a student’s next steps beyond high school.”
Oregon City High School and the Oregon City School District congratulate Crutcher on this outstanding recognition and thank her for the difference she makes each day for students, families and the Oregon City community.
This article is based on the official regional announcement from Clackamas Education Service District and the Oregon Teacher of the Year Program, a program of the Oregon Department of Education in partnership with the Oregon Lottery.