winningest

“Oh yeah? Well you guys may have won this time, but my team’s still the winningest!”

That’s how I imagine the first utterance of winningest, and the fact that the speaker, in my mind, could just as well have been a four-year-old as a drunken sports fan in a pub is telling. Winningest has a decidedly juvenile and unsophisticated ring to it, and, judging by the comments on Merriam-Webster’s entry for the word, a lot of people hate it, calling it a “made-up word” and a “lazy degradation of modern language.”

So why is it so objectionable?

Well, first, It hasn’t been around for all that long. Although the Online Etymology Dictionary claims winningest appeared in the written record by 1804, without seeing a reliable example, I’m more inclined to believe the Oxford English Dictionary and Merriam-Webster, which both trace the word back to the early 1970s. According to Webster’s in 1974 it appeared in The State newspaper in Columbia, South Carolina, which described the Maryland-Eastern Shore as the “winningest college basketball team in the nation.” Since the word was coined, it’s been used almost exclusively in (North) American sports pages.

Newness alone isn’t a good reason to find a word immature, though; after all, plenty of much newer words have seamlessly slipped into everyday usage. The resistance to accepting winningest as a “real word” probably comes from its weird morphology and incongruous semantics. We don’t usually slap the superlative -est morpheme onto the -ing morpheme—it seems like a mistake a young child might make—and winningest may be the only English word to feature this odd combination. Sure, present participle forms can serve beautifully as adjectives, but even words like charming and stunning—which we probably use more often as adjectives than as verbs—are compared using more and most rather than the -er and -est suffixes.

And speaking of which, if winningest exists, why doesn’t winninger? This lack of a comparative counterpart to winningest contributes to its oddness. What’s more, you could easily argue that the superlative doesn’t even make sense. We tend to think of winning as half of a dichotomy, not the end of a spectrum. Winning isn’t really a gradable adjective; if you’re not winning, you’re losing.

Yet this semantic mismatch is why winningest has found a niche as a functional word, despite the many reasons it shouldn’t exist. It doesn’t actually mean “most winning,” does it? To be the winningest means to have the most wins or victories, or to have the most success, typically in a sports context. And in that context, it’s unambiguous, succinct. You may wrinkle your nose at a phrase like “the winningest team in the league,” but you’re unlikely to be confused by it, and any other way of expressing the same concept would simply take more syllables.

Despite the objections to this “non-word,” it seems to be slowly seeping out from its sports confines into the rest of the world; even law firms are seizing the opportunity to declare themselves “the winningest.” The question is whether it’ll remain a one-off anomaly or spawn a new, productive way of affixing. Will we one day read about the eatingest competitor at the hot dog contest or the flyingest pilot in the air force?