The Maryland Association of Secondary School Principals named Dr. Deborah Dennie of Leonardtown Middle School as the 2026 Middle School Principal of the Year on Jan. 7, 2026, in Leonardtown, St. Mary’s County.
MASSP Executive Director Chris Truffer presented the award during a recognition ceremony at the school. The honor recognizes Dennie’s more than 25 years of leadership within St. Mary’s County Public Schools. Dr. J. Scott Smith, superintendent of St. Mary’s County Public Schools, stated, “Dr. Deborah Dennie’s two-and-a-half decades of leadership in St. Mary’s County Public Schools epitomize service, centered on compassion and competence. She is a mentor to rising leaders, an advocate for teachers, and a champion of students. This recognition is a testament to her work.”
Dennie will represent Maryland at the national level as one of the state nominees. She is eligible for the National Middle Level Principal of the Year award from the National Association of Secondary School Principals. The national winners in both middle school and high school categories will be announced during the NASSP National Education Leadership Awards Gala in Washington, D.C., in April 2026.
The MASSP award highlights outstanding secondary school leadership across Maryland, with one middle school and one high school principal selected annually. Recipients demonstrate excellence in instructional leadership, school management, community engagement and student advocacy. Dennie’s selection underscores her long-term contributions to education in Southern Maryland, where she has served in various administrative roles supporting academic achievement and staff development in St. Mary’s County Public Schools.
St. Mary’s County Public Schools serves approximately 18,000 students across 28 schools, including several middle schools in the Leonardtown area. Leonardtown Middle School, located in the historic town of Leonardtown, focuses on preparing students for high school through rigorous academics, extracurricular activities and character education programs. Dennie’s leadership has coincided with ongoing efforts to improve student outcomes in a county that has seen population growth and evolving educational needs tied to its proximity to Naval Air Station Patuxent River and other regional employers.
The award process involves nominations from peers, superintendents and community members, followed by review of applications that detail leadership accomplishments, school improvement data and personal philosophy. MASSP, affiliated with NASSP, supports secondary principals through professional development, advocacy and recognition programs statewide.
This recognition adds to a series of accolades for educators in Southern Maryland during the 2025-2026 school year, reflecting the region’s commitment to quality public education amid challenges such as teacher retention and post-pandemic recovery. Dennie’s achievement will be celebrated locally as an example of sustained dedication in school administration.
St. Mary’s County Public Schools officials noted that the honor brings positive attention to the district’s efforts to foster supportive learning environments. No additional details on specific initiatives under Dennie’s tenure were released in connection with the award announcement.
The national gala in April will feature presentations from education leaders and policymakers, with winners receiving monetary awards, professional opportunities and national visibility. Maryland has produced national winners in past years, though no St. Mary’s County principal has claimed the top national honor in recent cycles.
