Visiting beloved holiday spot Saratoga Springs has been a Rotondo family tradition for years, but Peter and his son know that luck doesn't always favor the faithful. The handicappers are gathering with the usual suspects for a two-day-long handicapping tournament with a massive $100,000 payout. Among the gamblers is Matt making his first tournament entry and Kevin "The Brooklyn Cowboy" Cox. When it comes down to the wire, Peter Jr. and Christian concoct a crazy scheme that may position them to take it all home--but there are dozens of other handicappers who have their own ideas. Meanwhile, handicapping veteran Michael is in the market for a prize horse. Is he ready to go big time, or will he get a lesson in true wealth?