Chester is the Assistant Principal of New Horizons’ Career and Technical Education Center at Woodside Lane. He was appointed to this position in August 2019 and brings with him 17 years of Education experience, all but one by way of Accomack County Public Schools.

In Accomack, he served as a 6th Grade Math and Science Teacher, a Marketing Teacher, and DECA Advisor, the Prevention and Intervention Specialist, and most recently the Coordinator of Students Services and Human Resources.

Chester is a 2001 graduate of Hampton University and 2012 graduate of Salisbury University, where he earned his M.Ed. in Educational Leadership. Chester is also a certified Academic Life Coach, and published author of two books.

He resides in Newport News with his wife, Nyoka, and his son, Mason.