The name Winston ranked 805th in popularity for males of all ages in a sample of 2000-2003 Social Security Administration statistics and 481st in popularity for males of all ages in a sample of the 1990 US Census.
Though this name has fluctuated in use, it has been quietly present throughout the last century.
In the Middle Ages Wynnstan changed in use from a personal name to a place name. With the modern form of that place name in mind, the future Prime Minister of Great Britain was christened Winston Spencer Churchill in 1874. (His mother's family had connections to the region.)
While this introduced Winston for personal use in the 20th century, it has not enjoyed widespread popularity. As in the cases of Patrick among the Irish and Victoria among the British, certain famous people create such strong associations with their name that parents are reluctant to choose it for their children during or close to the famous person's life time.
Will 21st century parents choose it more often, attracted by its namesake's reputation for courage and eloquence?
Winston Leonard Spencer Churchill (born 1874, died 1965)
British statesman, author and historian. Led the United Kingdom through much of World War II.