The biggest problem with gambling is that if it is done between friends it can cause you to get angry at one another. If your friendship is not strong, it will most likely collapse over an issue like this. I say if they are all friends they should make him walk across a football field with a marshmallow stuck up his butt, if he drops it he eats the dang thing. If they are not friends, I see no harm in fitting him with a new pair of cement shoes and tossing him into the nearest lake.