Principal's Page

Anthony Gray-Bolden is a visionary leader entering his fifth year as Dean (Principal) of the Cab Calloway School of the Arts, bringing 24 years of experience in education. A proud alumnus of Philadelphia’s Girard Academic Music Program, Dean Bolden’s foundation in performing arts 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, Immaculata College, and Liberty University, and is currently pursuing his Ed.D. in Educational Leadership at Delaware State University. 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, 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, and 2025 Delaware AP School of Access and Excellence.

As an active board member of the Arts Schools Network, Dean Bolden champions access to arts education and strategic partnerships. He is currently a member of the SPHINX LEAD Cohort 7, a prestigious two-year executive leadership program empowering arts leaders to transform the industry landscape. 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, attending church, deep-sea fishing, jigsaw puzzles, and bird watching.