John Massie Winston Jr.

October 5, 1945December 5, 2018
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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 7th 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. John is survived by his wife of 51 years, Karen C. Winston; sons, Andrew Winston and Patrick Winston and brother, Carey Winston (Faye). The family will receive friends on Friday, December 7, 2018 from 5-7pm at Nelsen Funeral Home & Crematory - Reid Chapel, 412 S. Washington Highway, Ashland, VA 23005, where a funeral service will take place on Saturday, December 8, 2018 at 1pm. Interment will follow in Woodland Cemetery, Ashland, VA. In lieu of flowers, memorial contributions may be made to Dare County EMS or Feline Hope Animal Shelter, 843 Herbert Perry Rd, Kitty Hawk, NC, 27949. Online condolences may be registered at


  • Visitation Friday, December 7, 2018
  • Funeral Service Saturday, December 8, 2018

John Massie Winston Jr.

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Laura Dough

December 8, 2018

Katen, Andrew and Patrick. I am so sorry for your loss. I worked under Mr. Winston in Dare and he was always kind and a gentleman. A good man .

Joy Simpson Toombs

December 8, 2018

Dear Mrs. Winston and Family,
I first met Mr. Winston when he was the visiting teacher for Spotsylvania County Schools. I worked in the central office and crossed paths with Mr. Winston often as he dropped by to see Mr. Neely. I remember some lively conversations occurring during those visits; especially if Mr. Neely, Mr. Winston, and Mr. McWhirt happened to be together. Those, of course, were the good old days of which I have very fond memories.

Please accept my deepest sympathy at this difficult time. May the memories of Mr. Winston's remarkable life give you comfort.

Shane Venable

December 8, 2018

Mr.Winston was my High School principal at Chancelor High. A true man of honor and integrity. He will be missed.
Shane Venable
Class of 1990

Judy Rodgers

December 8, 2018

My sincere condolences to his family. He was a sweet, good man who always had the best interests of both the students and faculty at Battlefield Intermediate and Chancellor High School at heart. We worked together in the PTO at both schools, I am so sorry to hear of his passing.

Betty Selby

December 7, 2018

Dr. Burgess, Karen and Family,
I was truly shaken and sorry to hear of the passing of Mr. Winston, our lunch partner and friend.
I was blessed and privileged to work with Mr. Winston at Dare County Schools for 17 years. His love for education and the professionalism he showed was amazing. He was a gentleman, treating everyone with respect regardless of job title.

When Mr. Winston retired from DCS he kept his pact with us, having lunch sometimes monthly other times quarterly.
Lunch was always filled with good times, belly rolling laughter and family updates. The lunch bunch will miss you, never forgetting you and your generosity, you will always have a seat at our table in spirit. Our menu is filled with memories that we will hold dear to each of us.

Until me meet again,
The Lunch Bunch
Betty, Deanie, Jean and Georgia


Kathy Marra

December 7, 2018

Mr. Winston was a brilliant school administrator. He was the best school leader that I worked for in my career. I will remember him as a great friend and colleague. Rest in piece. John Marra

Gerry Dotson Calavetinos

December 7, 2018

I worked with Mr. Winston at Battlefield MS, Chancellor HS and the School Board Office. As I watched the video, the words peace and serenity came to mind and that also describes Mr. Winston. As things were happening during the school day, he was the calm in the storm. He was a great administrator and a friend. I am so sorry for your loss but I know you have beautiful, sweet memories to cherish. I am a better person to have known him.
God Bless you all.

Walter McWhirt

December 7, 2018

My condolences to Karen, Andrew, Patrick, and Family,
I had the privilege of knowing John beginning in our early days of teaching. We had parallel careers, moving from teaching to administration. As principals, we would often call each other to discuss our problems and get insight on how to handle situations. I could always count on John to give me good advice. John’s strengths have been mentioned by others, but his calmness in any situation and his ability to clearly think through an issue and come up with the appropriate course of action was uncanny.
John and I both left Spotsylvania at the same time and took jobs in Dare County, North Carolina. John quickly established himself there as a knowledgeable educator and, as Assistant Superintendent, assisted in leading the educational system. He was respected and well thought of by all of those who worked with him.
I knew John as a friend and our families spent a lot of time together during leisure hours. We took vacations to the Outer Banks and often stayed at the Mariner Motel. Later years we spent a lot of time on the water, cruising the Potomac River and Chesapeake Bay. Those were good times and we enjoyed a lot of adventures.
John made a difference in the lives of the people he touched. He will be missed.

Terry Garfield

December 7, 2018

So sorry to hear of John's passing. As we opened Chancellor High School, he had more than his share of troubles...wires hanging from the ceiling, a gas leak in the auditorium that caused an evacuation of the staff the week before opening. He was always calm and reserved, but with that dry wit lurking just beneath the surface. I can see him now adjusting his tie before giving his comment or response. If there was a sparkle in his eye, you'd better be prepared for the humor. I never saw him flustered, even when the members of a graduating class each handed him a hard candy as they shook his hand crossing the stage. He seemed to take everything in stride. Stride on.

Stephanie Funai Coleman

December 6, 2018

I wish there was more we could do or say to help you all through this sad time. We hope you can find peace, comfort and rest in all the good memories you have with each other. Sending our deepest sympathies to each of you from Heatherstone.

The Funai Family