Q: I’m trying to find out the history of the word “winningest.” Merriam-Webster Online says the first known use of the word was 1972, but it doesn’t give any details. I have a hunch that it was first used to describe my boyhood hero, Richard Petty, the winningest stock car driver of all time. How can I find out if my hunch is correct?
A: The adjective “winningest” has been around for hundreds of years, a lot longer than Richard Petty, but it meant the most alluring or attractive when the word first showed up in the 1600s.
The earliest example we could find in Google Books is from The False One, a play about Caesar and Cleopatra, by John Fletcher and Philip Massinger. The work is believed to have been written around 1620.
In Act III, Scene 2, Antony says Cleopatra has “eyes that are the winningest Orators” and “a tongue that can deliver The Oracles of Love.”
We found thousands of other examples of “winningest” used this way over the centuries in books, plays, newspapers, magazines, and so on.
Our searches of Google databases indicate that the adjective “winningest” took on its sporting sense in the mid-20th century.
As owners of two Golden Retrievers who compete in obedience trials, we zeroed in on this early example from a July 1955 issue of the American Kennel Gazette:
“At present the dog with the winningest way in our club is ‘Cindy,’ that beautiful Golden Retriever owned and shown by Greta Taft. Cindy finished her C.D. in three straight shows in June with enviable scores, and now Greta is keeping her in trim by showing her in Graduate Novice until she is ready for the Open class.”
(A dog that qualifies in three Novice obedience trials earns a “Companion Dog” title. One that qualifies in three Open trials earns a CDX, or Companion Dog Excellent, title.)
Cindy beat out Richard Petty by quite a few years. Petty began his racing career in 1958 and was the NASCAR rookie of the year in 1959. But he and the adjective “winningest” apparently didn’t come together until the 1970s.
The earliest example we’ve found is from an article by Robert F. Jones in the April 9, 1973, issue of Sports Illustrated:
“Of course, Richard is already the winningest driver in NASCAR history (in terms both of races and personality), and his 150 victories over 15 seasons amount to more than double those won by Pearson, his closest rival.” (The reference is to David Pearson.)
We posted a brief item on the blog back in 2007 when a reader complained about the use of “winningest.” Many people are bugged by the adjective and don’t think it’s a legitimate word.
However, you can find “winningest” in many standard dictionaries, including The American Heritage Dictionary of the English Language (5th ed.) and Merriam-Webster’s Collegiate Dictionary (11th ed.), though some describe the usage as informal.
And as we’ve said, the adjective “winningest” has been around for hundreds of years, first in the sense of most attractive and later in the sporting sense.
The word “winning” first showed up sometime before 1300 as a noun that referred to getting money or wealth, but that sense is now obsolete, according to the Oxford English Dictionary. In the early 1300s, it took on the sense of victory in a game or contest.
When the adjective “winning” appeared in the early 1400s, it had the now-obsolete sense of gaining money or wealth.
In Elizabethan times, the adjective took on the sense of winning in a contest or competition. The earliest OED example of this new meaning is from Shakespeare’s 1599 play Romeo and Juliet: “Learne me how to loose a winning match.”
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