The Shadow
RICHMOND –– Alleghany Highlands Public Schools’ High School Principal Derek Cantrell has been named the 2026 Outstanding High School Principal of Virginia by a panel of principals and superintendents representing the Principal Awards Committee of the Virginia Association of Secondary School Principals (VASSP). Cantrell, who has led Alleghany High School since 2022, was recognized for his leadership in school consolidation, culture-building, instructional systems, student opportunities, and innovation.
Cantrell guided the historic consolidation of two rival high schools under the unified “Better Together” philosophy, creating a student-centered culture grounded in belonging, safety, and shared expectations. The consolidation produced a new school identity, increased community engagement, and strong cultural indicators including a five percent increase in daily attendance and a 14% decrease in referrals under the Student Behavior and Administrative Response framework.
His leadership extended to expanding college-level learning. Dual Enrollment English enrollment grew from 40 seats in 2023–2024 to 154 seats across ten sections—a 285% increase. Early Writing SOL results have also shown significant improvement. The Cougar Scholars initiative now supports students in meeting verified credit requirements earlier, helping ensure seniors begin their final year fully credentialed and college- or career-ready.
Students credit Cantrell for making the high school a place where they feel safe, supported, and known. One senior shared, “High school can be treacherous, but with the right support, many of us achieve amazing things. Mr. Cantrell and the administration provide the perfect amount of support and opportunities that allow us to feel comfortable in the transition from childhood to adulthood.”
Teachers also recognized Cantrell for fostering innovation, shared leadership, and student success. One teacher noted, “He has created chatbots that have helped our academic departments immensely. These innovative tools have helped teachers streamline planning, strengthen instruction, and better support students.”
Cantrell has presented his work on culture, consolidation, and AI-supported instructional leadership at state and national conferences including VASSP (2025), SREB Making Schools Work (2025), and VSTE (2025). His work has also been featured on national podcasts such as Better Leaders Better Schools, Principal Matters, and Proud Principals.
Superintendent Kim Halterman described Cantrell as “a steady and determined leader who is constantly thinking of ways to help our Appalachia students see their future more brightly and clearly through education.” Prior to leading Alleghany High School, Cantrell served as principal of Covington High School from 2016 to 2022, where he implemented Power Hour for enrichment and remediation, launched attendance and behavior incentives, and achieved three consecutive years of full accreditation.
Alleghany High School now serves as the unified high school for Alleghany Highlands Public Schools and continues to expand opportunities through career pathways, dual enrollment, AI-assisted instruction, and its nationally recognized AHA Advancement Programs. Cantrell will represent Virginia in the National Association of Secondary School Principals’ (NASSP) National Principal of the Year Program.
Superintendent Kim Halterman described Cantrell as “a steady and determined leader who is constantly thinking of ways to help our Appalachia students see their future more brightly and clearly through education.” Prior to leading Alleghany High School, Cantrell served as principal of Covington High School from 2016 to 2022, where he implemented Power Hour for enrichment and remediation, launched attendance and behavior incentives, and achieved three consecutive years of full accreditation.
Alleghany High School now serves as the unified high school for Alleghany Highlands Public Schools and continues to expand opportunities through career pathways, dual enrollment, AI-assisted instruction, and its nationally recognized AHA Advancement Programs. Cantrell will represent Virginia in the National Association of Secondary School Principals’ (NASSP) National Principal of the Year Program
