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We’ve got winning on the brain, but not because our lotto tickets finally paid off. It’s because of sports and Coach Carol Hutchins finding herself as the second-winningest active coach of softball and the winnigest coach in the University of Michigan’s athletic department history.

Winningest has been around since at least the mid-20th century, but winning in the Charlie Sheen sense, has been around even longer, says University of Michigan English Professor Ann Curzan. 

“The adjective winning, in the sense of victorious, goes back to Shakespeare’s time,” Curzan explains. “There is a nice quote from Romeo and Juliet using winning as in ‘learn me how to lose a winning match.’”

But winning isn’t all about sports and matches, we also use it to describe attractive attributes.

“You then have the sense of winning as in attractive or alluring,” says Curzan. “For me, that’s always a winning smile.”

If you're Julia Roberts you may even have a winningest smile, and that dates back to the 19th century.

But while winningest doesn’t quite roll smoothly off the tongue, it isn't exactly poor grammar.

“This may feel colloquial, but there is actually nothing wrong with it,” Curzan explains. “If we think about some other ‘ing’ adjectives such as fetching they tend to prefer more and most."

Although you wouldn't normally say, fetchingest you can still find it, along with “the lovingest mother in the world.”

But what about more better? Should it really be betterer? Betterest

“Here we’ve got a different issue with these comparative adjectives, which is the question of double comparatives," says Curzan. "If you take the word better it’s already a comparative. The adjective is good the comparative is better, and best. I think because it’s not gooder it’s better, occasionally you’ll see that double comparative and you’ll get more better."

More better is highly criticized by most grammarians, in spite of its long history.

Still, if it’s good enough for Shakespeare, why can’t it be good enough for us? After all, he once said, “to some more fitter place” and “more corrupter ends.”

But whether you prefer better or betterest or more betterest, we remain, ever your lovingest, Michigan Radio.

– Cheyna Roth, Michigan Radio Newsroom 

Anne Curzan is the Geneva Smitherman Collegiate Professor of English and an Arthur F. Thurnau Professor at the University of Michigan. She also holds faculty appointments in the Department of Linguistics and the School of Education.