Roughly synonymous with "getting your ass kicked". Winning! is often a result of pissing off everyone you know and getting canned. There is a fine
line between Winning! and OD'ing! or Dying of some kind of
VD! Side effects include being arrested and losing all
respect.
Man 1: I just got fired for being an arrogant prick and abusing every substance known to man, such as alcohol, prescription pills, sex, and enough cocaine to keep
Colombia's economy thriving. Not to mention the
time I threatened to cut my wife's head of with a pen knife and mail it to her
mom...
Man 2: Dude, your winning even more than charlie sheen.