On paper, it sounds like the perfect plan: who better to make judgements on race horses than another race horse? I'd trust a boxer's opinion on a boxing match, after all, so the opinion of Wintervale the horse is probably one worth taking into account. This scheme could, of course, only be thought up by inveterate silly person Max Fosh, and represents a bold new step in the art of gambling. Wintervale was taken to a horse-friendly betting parlor (because supposedly such things exist) to see if Max could at least recoup the cost of renting him out by placing bets on the horse's peers that the horse himself selected.
Just don't think about the ethics of technically teaching a 4-year-old how to gamble.