I disagree. On multiple things. "winning" was already a slang buzz word pretty much, he just made it more famous by using it in a hilarious and awesome interview

Sheen vs. Career - losing <---- He's the most famous he's ever been getting the most attention he's ever gotten. If that's not winning I don't know what is
Sheen vs. addiction - losing <---- eh, I guess I'll agree with that one. who knows what all that guys on. Besides that crazy charlie sheen drug.
Sheen vs. wife - losing <---- banging multiple porn stars.... Definitely winning; If marriage is not someone's priority, don't see why not being married would be losing.
Sheen vs. kids - lost <---- no more kids means more time to party. Winning by his standards
Sheen vs. Life - Loser <---- he's rich and having fun 24/7. Again if that's not winning I don't know what is.

plus, he helped the indians win a couple times, and fought sadam hussein.