John Massie Winston Jr.

Published 6:36 pm Sunday, December 9, 2018

John Massie Winston Jr., 73, of Nags Head, passed away on December 5, 2018. He was the son of the late John Massie Winston, Sr. and Virginia Ramsey Winston and was preceded in death by his sister, Mary Margaret Winston Pockrass.

John was a graduate of Patrick Henry High School and Randolph-Macon College and earned a Master’s Degree from the University of Virginia. He enjoyed spending time on and near the water in his boat and at the Outer Banks.

John had a distinguished career of 48 years in public education, serving for 32 years in Spotsylvania County Public Schools in Fredericksburg, Va. and for 16 years in Dare County Schools in Nags Head, NC. He began as a seventh grade math teacher at John J. Wright Middle School in 1968. After four years, he became a visiting teacher for the school district before being assigned as acting principal at Livingston Elementary School. He served as principal for a total of 27 years, including stints at Chancellor Elementary, Spotswood Elementary, Battlefield Middle School and as the principal who opened Chancellor High School in 1988. In 1995, he was tapped to become the Director of Secondary Instruction. In 1997, he was promoted to Assistant Superintendent for Personnel, a post he held until he retired from Virginia Public Schools in 2000. Later that year he became the Assistant Superintendent of Dare County Schools, where he worked for 16 years before retiring from North Carolina Public Schools. Those fortunate enough to work with him described him as always remaining calm and giving good advice, all the while maintaining a quick, but wry sense of humor.

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John is survived by his wife of 51 years, Karen C. Winston; sons, Andrew Winston and Patrick Winston and brother, Carey Winston (Faye). Online condolences may be registered at