Principal's Page

Anthony Gray-Bolden is a visionary leader entering his sixth year as Dean (Principal) of the Cab Calloway School of the Arts, going on 26 years of experience in education. A proud alumnus of Philadelphia’s Girard Academic Music Program, Dean Bolden’s foundation, established at a performing arts school, has shaped his deep commitment to advocating and championing for students to have access to the benefits of an arts-integrated learning experience.

He holds degrees and certifications from West Chester University, Penn State University, Immaculata College, and Liberty University.  He is currently pursuing his doctorate in Community Care and Traumatology. His professional journey includes roles as a special education teacher, Dean of Students, Middle School Assistant Principal, Elementary School Principal, and now Dean (Principal) of Cab Calloway School of the Arts.

Dean Bolden is the 2025 Delaware NASSP Principal of the Year and a 2024-25 Delaware National Association of Federal Programs Administrators Leadership Award recipient. Under his leadership, in collaboration with staff, students, parents, and alumni, Cab Calloway has achieved national distinction, earning recognition as a 2022 National Blue Ribbon School, 2024 AP Governor’s School of Excellence in Civic Education, 2022-2025 Delaware AP School of Access and Excellence, and 2022-26 US News Best Schools.

As an active board member of the Arts Schools Network, Dean Bolden champions equitable access to arts education.  He is currently a member of the SPHINX LEAD Cohort 7.  This program has shaped his vision for CCSA in preparing global leaders through innovative, student-centered art-integrated programming.

Outside of his professional work, he treasures time with his family, mentoring youth through his nonprofit Prodigal Sons Initiative and Kappa Alpha Psi Fraternity Inc Kappa League Leadership Development Program. He also enjoys jigsaw puzzles, bird watching, music, and living out his faith in God.