Raymond Whitaker, Sr., began his career in public education at Essex County Public Schools as a mathematics teacher and was the Chairman of the Math Department for over 10 years.  He taught for 22 years and his motto remains, “You have to meet kids where they are and get them to where they need to go.”  During his tenure at Essex High School, he coached football, softball, Girls Varsity Basketball, and Boys Junior Varsity Basketball.  Raymond was also a Little League Baseball Coach for approximately 21 years.

In 1991, Raymond was named Acting Assistant Principal of Essex High School and later became the Assistant Principal.  In 1997, he became the first African American to be named Principal of Essex High School. After 33 years of service, he retired as the Principal from Essex High School in June 2002.  Upon his retirement he served as a Mathematics Consultant for the surrounding counties, and continues to mentor and tutor countless students.  Raymond has been a member of the Essex County School Board for 15 years, serving as Chairman for three separate terms.  He is the President of the Kiwanis Club Tappahannock, member of Multi-Jurisdictional Grand Jury and Selective Service System Local Board Member of the Commonwealth of Virginia.  Raymond attends Angel Visit Baptist Church in Dunnsville, VA., and is the Chairman of the Deacon Ministry, Financial Secretary, member of the Trustee Ministry, History Ministry, and Men’s Choir.

Raymond earned a Bachelor of Science Degree in Mathematics from Shaw University and received his Master of Education in Administration and Supervision from Virginia State University.  He is married to Caretheus (Kay)Williams Whitaker.  They have three children, Ramona (married to Joseph, Sr.), Raymond, Jr. (married to Janelle), and Ranardo.  They also, have five grandchildren, Joseph, Jr., Jordan, Amaya, Aleyah, and Raymond.