I suggested the t-shirts and mugs as they would not cause any undue influence.
Sure they would. Just put a message or logo on a shirt they don't like and you're done. Advertisers and suppliers get complaints all the time and cancel conservatives.
The bets would range from first pawn taken, first to castle, first to lose/capture a knight, bishop, queen, etc.- you get the idea.
I bet here on FR, there are numerous chess players...we could set up a tournament...
Someone else would have to run it, as I have no programming skills, eg: setting up a graphic board that would show the moves, but we have a ton of puter-savvy folks here.