Written by David Milch
Directed by Michael Mann
Chester "Ace" Bernstein is released from a three-year prison sentence and is picked up by his longtime driver/bodyguard Gus Demitriou, who, it's revealed, is acting as the front for Ace's ownership of a new Irish race horse, Pint of Plain.
Excited about getting a chance to ride for the trainer Turo Escalante, apprentice jockey Leon "Bug Boy" Micheaux annoys Escalante with his small talk about running big with his horse Mon Gateau in a race later that day. Escalante berates jockey agent Joey Rathburn for Bug Boy's indiscretion. Rathburn orders the young jockey to watch his mouth - what if Escalante was making a bet?
A foursome of degenerate gamblers - Marcus, Jerry, Renzo and Lonnie - pitch in to place a Pick Six bet using Jerry's picks. Jerry's choices seem a longshot, hinging on a win by Escalante's Mon Gateau in the fourth (the horse has been out of racing for two years and is being ridden by an apprentice jockey). But Jerry is betting on the trainer, and if Mon Gateau wins, they knock out most of the other tickets. Jerry, who is broke, sells his picks to Kagle (a track security guard/loan shark) for $50 to bet on Mon Gateau in the fourth in order to win his share of the Pick 6 contribution.
When Rathburn sees the brilliant workout by the Old Man's horse, he calls his veteran jockey, Ronnie Jenkins, ordering him to sober up and get down to the track: He's just seen a winning Derby horse run.
After getting settled back at home in his hotel suite, Ace visits Nick DiRossi's restaurant/office. Ace thanks him for help getting Gus set up with a $5 million jackpot -- winnings that provided a cover story for Gus's buying of the horse. The two discuss Ace's plan to buy the Santa Anita race track and put a casino in - and how Ace's criminal record may mean he'd have to remain in the background of the deal. When Ace reveals his tape recorder - a "memory aid" - DiRossi looks distrustful and Ace becomes enraged. DiRossi assures him that he knows what Ace has sacrificed.
Gus visits Escalante and Pint of Plain. Escalante makes it clear he knows the driver's a beard, and there's a shadow owner.
Mon Gateau wins in the fourth, setting the degenerates up for a win. In the last race, Bug rides another horse, Tattered Flag. The jockey Ronnie, coming off of an injury, shows up to watch. Bug is devastated when his horse breaks a leg and has to be put down.
The degenerates realize they have won the whole Pick Six pot - but they lay low, not wanting to draw media attention (and thus the IRS) to their winnings.