Assistant Principal of Student Services
Ms. Shambria Simmons
Ms. Simmons serves in School Operations and Student Services at Chaffee Trail Middle School and is in her 11th year in education. Math is her love language, and she values problem-solving, organization, and data-driven decision-making to support student success.
She works closely with administrators, teachers, and support staff to ensure smooth daily operations and strong student services. Ms. Simmons is proud to serve the Chaffee Trail Middle School community and remains committed to fostering a safe, supportive, and high-performing school environment.
Assistant Principal of Curriculum
Mrs. Rebecca Durkin
With over two decades of experience in education, Mrs. Durkin brings a wealth of expertise to our leadership team. A graduate of the University of Georgia and the University of North Florida, she began her career in 2001 teaching 7th-grade math at Highlands Middle School. Since then, she has served as a middle and high school math teacher and a high school math coach, building a career defined by a deep commitment to student achievement.
Her administrative journey is uniquely comprehensive, as she has served as an assistant principal at the elementary, middle, and high school levels. Her leadership has reached every corner of the county, with tenures at First Coast High, Loretto Elementary, Lake Shore, and Fletcher Middle.
At home, she and her husband, a fellow educator she met early in her career have been married since 2003. They are the proud parents of three children: Finn, a sophomore at UCF, and twin daughters Piper and Clare, who are high school seniors. When she isn't cheering on the Georgia Bulldogs or the Jaguars, she loves traveling abroad and seeking out the tallest roller coasters at amusement parks.
Dean of Students
Mr. Bilal Abdul Hakeem
Dean Hakeem serves as the Dean of Chaffee Trail Middle School and brings a deep commitment to youth development, academic excellence, and student leadership. He is a graduate of Howard University, where he earned a Bachelor of Arts in Criminal Justice with a minor in Education.
His professional experience includes teaching Science at both the middle and high school levels, as well as leading a wide range of after-school programs. Among these experiences is his work with the Johnson Family YMCA Teen Center, where he supported student growth through enrichment, mentorship, and community engagement. Dean Hakeem is passionate about empowering young people and fostering inclusive, engaging environments that promote both academic and personal success.
Dean of Students
Mr. Thomas Wilson
Thomas E. Wilson Jr. is an education professional with over 20 years of experience serving students across Pre-K through high school settings. He holds a bachelor’s degree in Psychology and a master’s degree in Education and Curriculum, and is currently pursuing a doctoral degree in Educational Leadership.
Throughout his career, Thomas has served in a variety of roles including classroom teacher, ESE lead teacher, dean of students, and mentor program leader. His work centers on student advocacy, restorative practices, data-informed decision-making, and building sustainable systems that support student success—particularly in high-needs and Title I school communities.
Thomas believes meaningful change in education occurs when relationships, structures, and purpose are intentionally aligned. He is committed to lifelong learning and to leading with empathy, integrity, and a growth mindset.
“Leadership is not about control, but about creating the conditions where others can grow.”