WHAT IT MEANS:
In the new interpretation, Winning means being successful at something that might not seem like a success.
ORIGIN:
Winning was regenerated in March of 2011 by Charlie Sheen. He refers to the word to describe his then current situation which involved scandalous activities like being publicly intoxicated numerous times and trashing hotel rooms. He conducted many interviews during this time and said he was “winning” and wasn't addicted to any drugs and denied all of his charges.
EXAMPLES FROM TWITTER:
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