Since I would guess quite a few people here would be interested in the Breeders Cup, how about a bulletin board contest? Everybody is probably going to handicap these races (to some extent) in advance anyway, right?
TG makes the rules and puts up the prize (free sheets for...?). Another possibility (which I like better) would be an entry fee, with the winner taking the pot home.
The pools should be big enough that nobody should have to worry about hurting their prices. Could provide a good focus for handicapping and betting strategy discussions as the Big Day nears. Or we could just call each other names. Just a suggestion. HP