- Back on the train, Henry takes some replica decks of cards from his buddy J.J. and gets to work on how he's going to cheat Doyle Lonnegan at poker.
- Meanwhile, Billie bumps into Lonnegan on the train and lifts his wallet from him. Billie passes the wallet on to Johnny, who walks the thing back to Henry. Henry opens the thing and finds more than fifteen thousand in Lonnegan's wallet.
- Next, Henry soaks himself in gin to make it seem like he's a total drunk. Then he waters the rest down and brings the bottle with him.
- He stumbles into the card game and makes a bit of an idiot out of himself. He also introduces himself as "Shaw."
- (We're going to refer to this fake character as "Henry-as-Shaw" to avoid confusion.)
- Lonnegan is offended, but still happy to take the guy's money.
- As the game begins, Henry-as-Shaw reaches for his pocket to get his money out. But the bookkeeper tells him it won't be necessary because everyone assumes everyone who's playing can cover their debts.
- We cut back quickly to Chicago, where it looks like the fake horse race betting place is coming together. In a back office, Kid Twist interviews a bunch of grifters to see if they're cut out for the Lonnegan job.
- Now we're back at the card game, where Henry-as-Shaw gets into a bit of a betting war with Lonnegan.
- After beating Lonnegan in a big hand, Henry-as-Shaw starts teasing him and botching his name—he calls him "Lonnehan"—until Lonnegan snaps and tells him he'll cut it out if he knows what's good for him.
- If Henry's plan is to annoy Lonnegan, it's definitely working.
- Back in the fake betting place, Johnny's old partner Joe Erie applies to be part of the big con and gets accepted by Kid Twist.
- Meanwhile, Henry-as-Shaw continues to make a rude jerk of himself at the card game. Lonnegan asks for a quick break and then brings his two goons into another room.
- He tells them to rig the deck so he can take out the rude guy at his card game once and for all.
- He wants the men to deal Henry-as-Shaw cards that are just good enough to keep him in the next hand. But Lonnegan's plan is to have cards that are just enough to beat him and clean out all his money.
- When the cards are dealt, Henry has three 3's and Lonnegan just has two 9's. But they both make big bets to start anyway, which gets the attention of the other rich dudes.
- When the men get their next round of cards, Henry ends up with four 3's, which is a monster of a hand. But Lonnegan ends up with four 9's, which can beat him.
- Just as planned, Henry-as-Shaw continues to raise the stakes until they're past fifteen thousand dollars.
- When the bets are in, Lonnegan triumphantly lays down his four 9's.
- But Henry-as-Shaw lays down four jacks …which is definitely not what he was holding two seconds earlier.
- Both Lonnegan and his goons know that Henry-as-Shaw cheated, but they can't call him on it because they'd have to reveal they were cheating to the rest of the group.
- Just like that, Henry-as-Shaw says that Lonnegan owes him fifteen grand. Searing with rage, Lonnegan reaches into his pocket and realizes he doesn't have his wallet on him anymore (remember that?).
- So now Henry-as-Shaw already has the man's fifteen grand and he wants another fifteen. Lonnegan says he'll have to go back to his room to get the money, but Henry-as-Shaw isn't buying it.
- He says he'll send a boy around in a few minutes for the money, or else it'll be news all over town that Doyle Lonnegan doesn't pay his debts.
- Henry-as-Shaw cashes in the rest of his chips and walks back to his room.