Ever play Monopoly? Did you ever take all of someone's money in it?

Of course you did. It's part of the game that some people lose their money/houses/hotels. Sometimes you can recover from that, sometimes you can't. In either situation it's a game. Nothing happened to the player aside from some mild annoyance at losing.

You just fought someone, and lost. They don't get to come over and hit you or anything, but they have won your character's gear and any money your character had on them. What the winning party chooses to do with it at that point is up to them/their character. They don't have to be nice, it's not yours anymore. That gear is theirs. Trying to convince an AP to make a donation of something they've won to a shokite would be amusing at best. Would you go giving armor to a sworn enemy? What IC thought process did you go through to make that decision?

"You're bankrupt? Here, have a gold-colored $500 bill. I don't want to hurt your feelings, as a player." In monopoly it makes no sense, it seldom does in CF either. It is a game. You will lose, on occaision. I'm more worried about the issues of someone that's WAY too attached to their gear than I am about someone who can roleplay the exchange between in-game enemies well.

-Falstaff