Winston, also known as Yankee, was born April 19th, 1941, to Linette Mascoll and Moses Sutherland in Campden Park, Saint Vincent. Winston was the 5th child of 7 children. For better opportunities, he moved to Trinidad where he learned his trade in construction. He later moved to England, then to the USA where he continued in his trade as a contractor. Winston was well known in the Boston community for his workmanship.

Winston was a member of the Unity Sports Club where he played dominos and cards. He has a lot of trophies. He was also known for his elaborate cookouts which were held on Boston Carnival weekend. People came from near and far to attend his cookout. Winston loved visiting his homeland in Saint Vincent to visit family and friends.

Winston is survived by his children: Sharon, David, Charmaine, Newasann, Sherrylann, Annisa. Siblings: Belma (deceased), Majorie, Evered (deceased), Irma, Fred (deceased), Venus. Wife: Joyce C. Sutherland (deceased). A host of nieces, nephews, grandchildren, and great-grandchildren.