A phrase started by the TV-show actor Charlie Sheen. This word can be used in describing anything that is great. "Not winning" is obviously used to describe something not as great.
Bob: I totally banged that hot chick, Ashley, last night.
Sam: Dude, that's winning.
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John: Man, I can't believe Samantha dumped me...
Ryan: I know, bro. That's not winning.
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