My early years were shaped by work on the family farm.  I vividly remember getting off the school bus and doing chores with my three older siblings.  By the time I entered high school, the family farm had sold.   However, my parents still expected me to have a job and work hard.  Through jobs at the local grocery store or bread factory, my high school years passed quickly.  The August after I graduated, I decided I should go to college.   Although I knew very little about higher education, I packed my car and moved to Springfield, Missouri to attend Evangel University.   My sister had attended there for a few semesters and to an 18-year-old kid, that makes perfect sense that I should go there. Fast forward a few years, I graduated with a Bachelor of Science degree in English Education.   I was the first in my family to graduate with a college degree. 

Although I had the degree, I could not find a job as a teacher.   At that time, teaching jobs we scarce.   Therefore, I worked other jobs and substituted as often as possible. Eventually, I was given the opportunity to be a high school English teacher at Owasso High School.   OHS provided with great colleagues, administrators, students, and much needed experience.  Within a few years, I became the proud father of baby boy and twin girls.   With three kids under the age of two, I was a teacher by day, alternative school director by night, and bus driver extraordinaire.  Although I did not have time to breathe, I started class to obtain my Master of Educational Leadership.   Upon completion, I served as assistant principal, principal, and superintendent.  After 10 years as Crooked Oak Superintendent, I still love this place and feel like we have just begun to scratch the surface of realizing our potential.  I plan to be a RUF-NEX for the rest of my career. 

My strengths and values guide me.  I genuinely enjoy students and firmly believe my work has a positive influence on the trajectory of a student’s life.  Furthermore, I believe we are put on earth to serve others.  Much like those administrators and colleagues poured into my life as a first-year teacher, I want to give back to teachers, students, and community members like I have been blessed.

 After twenty plus years as an educator, I can say without reservation that I am blessed to be a part of such a tremendous profession.

My name is Chace McCaskill, and I'm a lifelong Oklahoman who is incredibly proud to be part of the Crooked Oak community. After graduating with my bachelor's and master's degrees from East Central University, I started my career teaching math and coaching in my hometown. In 2019, I was lucky enough to find my way to Crooked Oak.

This place has become a second home to me. I spent my first two years teaching math and coaching our high school boys' basketball team. After that, I had the privilege of serving as the middle school principal while continuing to coach. I'm so proud of what we accomplished, taking a team with a 3-18 record to a six-year run with a 120-44 record, five district championships, and two state semi-final appearances.

Now, I'm excited to step into my new role as Assistant Superintendent for the 2025-2026 school year. While my role is changing, my commitment to our students, staff, and community is not. I will always be available to help in any way I can, and I look forward to working together to make Crooked Oak an even better place. We have a great staff, amazing students, and a supportive community, and I cannot wait to get started.

If you would like to schedule time to speak with Mr. McCaskill, please do so here at "A Chat with Chace."

Schedule a "Chat with Chace"