After finishing second two years in a row (to the same guy), Christian looks to finally win the Breeders' Cup Betting Challenge--the biggest live-money tournament of the year. When the handicappers regroup, tensions arise when Kevin learns Christian is teaming up with other entrants. Kevin decides to take a long shot at the Juvenile Phillies race--but freaks out when he learns his jockey might be disqualified. Then, it's on to the last race which features celebrity guests Toni Braxton and Richie Sambora. Will Christian, Kevin or John win big?