Delaware
Meet the public school leader named Delaware’s 2025 Principal of the Year
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Anthony Gray-Bolden thought he was hosting a state official at Cab Calloway School of the Arts on Monday morning. The dean reportedly expected a school assembly to kick off the day with students, faculty and staff.
He did not anticipate a statewide honor.
The leader in Red Clay Consolidated School District has been named 2025 Delaware Principal of the Year, an honor from the Delaware Association of School Administrators. A surprise assembly announced as much to the magnet school’s head, around 8 a.m.
In a public school district serving some 15,000 students, and a state serving thousands more, Gray-Bolden was recognized for “exceptional leadership and dedication to excellence in education,” according to Red Clay officials.
The dean brings about 24 years of experience in education to the halls of Cab, an arts-oriented magnet school in Wilmington, now in his fourth year. The musician and vocalist at heart is also an alumnus of such a program – the Girard Academic Music Program, a performing arts magnet school in Philadelphia.
Gray-Bolden has a dynamic résumé from there, according to Cab. He attended West Chester University on an athletic scholarship to play basketball while earning a bachelor’s degree in criminal justice. Later, he earned a special education certificate, a master’s in education, an educational leadership certification and more. He just started working toward a doctorate in education at Delaware State, too.
The dean has taught special education, served as dean of students and rose to leadership roles like assistant principal and principal. At Cab, his vision is “normalizing opportunities for creators as entrepreneurs and elevating the existing programming,” the school writes online, with an eye for students making a global impact.
He does love puzzles. When he’s not at school, not in a surprise assembly, Gray-Bolden loves hanging out with his wife and three sons, deep-sea fishing, playing the piano, singing and nursing a budding interest in bird watching.
The 2025 Delaware Principal of the Year is a busy guy.
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