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Re:The ‘-ize’ have it (2012) by meditative on Sunday August 09, 2020 @08:12AM (#24099078)
Slightly off topic, but since there are linguists here I thought I'd ask. Does the word winningest seem wrong to other people? It's such a foreign word to me that feels absolutely wrong. I only really hear it when watching US sports.

I'm from Australia, where we follow en-GB relatively closely for perspective.

Re:The ‘-ize’ have it (2012) by pacaro on Sunday August 09, 2020 @12:26PM (#24100681)
It feels ugly to me, but there doesn't seem to be a concise alternative.

It's usually used to refer to a person's record of wins, as in the coach who has lead a team to more wins than any other coach, at which point they are the winningest.

He's the...

winningest coach

most successful coach when measured by how many wins

coach with the best win-loss ratio

¯\_(ツ)_/¯

Re:The ‘-ize’ have it (2012) by cik2e on Sunday August 09, 2020 @01:13PM (#24101063)
“Most winning” would be the correct alternative, with the same number of syllables although to me it does feel more concise. As an American, I also hate this made up word.
Re:The ‘-ize’ have it (2012) by PhineasRex on Sunday August 09, 2020 @01:25PM (#24101156)
While it looks weird written down, "winningest" feels lovely in the mouth
Re:The ‘-ize’ have it (2012) by Lammy on Sunday August 09, 2020 @08:55AM (#24099305)
"ultimate"?

Then the runner-up is the penultimate.