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Darin Drill
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Darin Drill

My name is Darin Drill. I am a 4th generation Oregonian who has benefited tremendously by public education. I was raised near Salem, Oregon in a very middle class family. All my grandparents worked hard at blue collar jobs with the dream that they would see their children obtain the American dream. My father was the first to attend college and he brought that determination and work ethic to me and my sister to attend as well. After completing public school, I attended an Oregon public college, and then went to a private Oregon university and completed my Juris Doctor degree. During law school I coached at a high school to earn money to support myself. While coaching I found my love of education and upon finishing my law degree, I went back to school to become a public school teacher. As a teacher and a coach, I built strong and lasting relationships with students and staff, which made me want to be a more effective educator. My superintendent asked me to move from the classroom to the district office to be the Personnel Director, due to my law degree. From there, I became an assistant principal, a high school principal, a director of secondary education, and for the past 15 years, the Superintendent at Cascade School District. I am married to my wonderful wife, Amy, and we have been together for over 30 years. Our daughter Faith, just graduated from an Oregon private university and started her educational career this fall as an elementary special education instructor. Over the years I have collected and follow a couple of personal mottos that I try hard to live by. The first is, ‘living well is the best revenge.” I work hard to live an honest and healthy life and focus on the positive, regardless of the situation. Life at work can be filled with negative and frustrating people, but staying focused on living well and working well with others actually does help me be effective. The second motto is, “all things in moderation, including moderation!” As I get older, this motto is easier to follow, but I still find myself working on this one all the time. My hope and goal is that the day I leave my position as Superintendent at Cascade, I will have left it in better shape than when I inherited it. To do that I focus on the students that attend Cascade every day. I am determined to see them all succeed!

Past AASA Oregon Superintendent of the Year Winners:

2023 Oregon Superintendent of the Year: Dr. Sara Johnson

2021 Oregon Superintendent of the Year: Christy Perry

About the Award:

The Superintendent of the Year program, sponsored by First Student and AASA, pays tribute to the talent and vision of the men and women who lead the nation’s public schools.

State-level winners are selected on the following criteria:

    • Leadership for Learning
    • Communication
    • Professionalism
    • Community Involvement

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