Principal Spotlight: Derrick Orr

Written by Chicago International Charter School
26 October 2022
Posted in Educator Spotlight

CICS Wrightwood is a K-8 elementary school that opened in 2005 on Chicago's South Side. The school is led by Principal Derrick Orr who ensures that his dedication shows the school's intentions for preparing students for high school and beyond by emphasizing achievement through action and accountability. 

A partnership of teachers, staff, families and community work together to create a nurturing environment where all students are offered rigorous and engaging learning opportunities that foster student understanding of themselves and the world. Principal Orr pushes his students and staff to demonstrate the intellectual skills, cultural competence, belief in self and the engagement in community necessary for success in school, college, the workplace and life. 

Read more from Principal Orr and learn more about his dynamic leadership. To learn about CICS Wrightwood you can visit their Facebook page and website

1. Why did you decide to become a principal?

My mother was a former teacher. I remember as a student I would complain to her all the time about my student experience. Her answer was always the same. “If you don't like the way things are being run, put yourself in position to make it better.” I will never forget those words. That is what pushed me to be an educator and a Principal.

2. What is one thing you are looking forward to in the new school year?

Positively impacting the life of a student. I have always wanted to change the life of a student the way someone changed my life. I believe in giving back and being an example of what hard work looks like.

3. What is one skill that you have that makes you a great principal? 

That is a hard question. I guess if you were to ask a staff member they would probably say my ability to get everyone on the bus. My dedication to my craft and my love for students is a close second.

4. Name something that you are proud of on or about your campus.

I think we have the best parents and staff of any campus in Illinois. They are always willing to get better, accept feedback, and push students to give their very best. You couldn't ask for more than that. I have amazing teachers that give 110% each day. 


5. How do you make positive connections with your students?

I believe in relationship building.   When students are in class, I am in class giving feedback to teachers and engage students in learning. When they are at lunch and recess, I am also spending time with students eating and playing with different activities. I believe that when students believe that you care they will go the extra mile for you. I try hard to know my students both academically and socially.  

6. How are you making those connections now?

I make connections daily,  with students, staff, families, and community partners. I always look for a way to close gaps and make us better as a school. Connections and relationships are key.

7. What is your vision for student success this year? 

To make sure all of our students are reaching their On-Track Metrics.  To have a school that students feel safe in and want to attend on a daily basis.  To build solid partnerships that help us reach our full potential, to build the capacity of teachers and make data driven decisions. 

8. Education is ever-evolving. If money/resources/time were not an issue, what would you do to improve your school?

I would start my own Charter school. I would create a school of Global Learners. I would like my students to receive educational experience in the United States and visit other countries around the world so that they have full experience and exposure to other cultures.


Derrick Orr currently serves as the Director of CICS Wrightwood Elementary School. Mr. Orr oversees all academics and operations within the school and supports 27 teachers, 16 para-professionals, three Instructional coaches and two assistant principals in their leadership roles at the school. When Mr. Orr arrived at Wrightwood the school was a level (2) school. Prior to the pandemic, Wrightwood had moved to a level 2+ status and 2/10 points from reaching level I. 

Director Orr is responsible for improving and supporting all aspects of teaching and learning school-wide. His commitment to over 725 students is to ensure equity in access to high-quality educational opportunities. Prior to coming to CICS Wrightwood Director Orr previously was the head principal at Manierre Elementary School in the Cabrini Green area from 2012-2018. When Director Orr took over leadership responsibilities at George Manierre Elementary School; it was on probation for over ten years, was a level (3) school and was slated to be closed. In his first four year tenure at Manierre the school was saved and off of probation, was a level one school and was 1/10 of a point from receiving the highest rating of Level 1 +. Taking over as school leader was a natural transition from his previous role as Assistant Principal, Instructional Coach and Dean of Students. Mr. Orr began his teaching career in Chicago Public Schools as a self-contained Special Education teacher for the first (10) years of his career. Mr. Orr is a proud graduate of CPS where he attended both elementary and high school in Chicago. 

Director Orr received several prestigious awards from the mayor for improving student growth in both reading and math and has helped transform many schools that struggled academically and culturally to become successful. 

Since coming to CICS Wrightwood Director Or has helped develop the Middle School College Tour that takes students across the country to visit some of the top Universities and HBCUs. Director Orr goal is to make sure every student has a chance to experience a visit to a university. With the overwhelming amount of violence in Chicago, it is extremely important that students get a chance to see a different life outside of their communities. In addition, if students have a chance to witness the greatness of college in 8th grade they will be better prepared and focused for high schools which traditionally don’t do college visits until their junior year.  Director Orr has also built partnerships with The Chicago Bears, Marianos, Trader Joe's, Monumental Faith Church, Global Girls, and Fifth Third Bank just to name a few organizations. 

Director Orr also believes in developing Change Makers and Agents of change with his Civic Engagement projects such as feeding over 200 families, Partnering with neighborhood churches to provide music and dance programs and fundraising thousands of dollars to Cancer just to name a few. Director Orr is definitely someone we all can be proud of. His dream is to one day own his own Charter school where he continues his quest for excellence.

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