Al Capone enters the Four Deuces in Chicago. He ascends the stairs and draws a pistol from his coat. He goes into the room of Pearl, one of the prostitutes, where Jimmy is asleep next to Pearl. Pearl wakes up and Capone holds a finger to his mouth to quiet her. He raises the pistol and fires into the pillow next to Jimmy. Jimmy is startled awake by the shot and falls out of the bed. Capone finds Jimmy's response hilarious. Jimmy is furious and throws a glass at Capone, missing him.

Capone explains that he came for the car keys and tells Jimmy to go back to sleep. Jimmy reassures Pearl and then notices his ear is bleeding.

Pearl cleans Jimmy's ear and asks if it is painful. She suggests that he could try opium at a den in Chinatown. Jimmy is dubious and she says that it is divine. Pearl confesses that she is sometimes afraid of Capone and Jimmy says that Capone is alright and that his roughness comes from growing up in Brooklyn, New York.

Pearl asks where Jimmy is from and then reveals that she comes from a small town in Wisconsin. Jimmy asks what it is like and Pearl tells him that her grandfather was the first white man in her hometown, her father was the first townsman to go to prison and that her mother was killed in a car accident and jokes that she has a lot to live up to.

She asks Jimmy about Princeton, having heard Capone use it as a nickname. Jimmy admits that there was a person who had ideas about his path in life. Pearl guesses that Jimmy is talking about his father but he says his father would not do that explains that he means Nucky, comparing Nucky to Johnny Torrio in Chicago. He says that his relationship with Nucky is over now.

Pearl asks Jimmy what his ideas about himself are and he says it is a good question but does not answer. Pearl admits that she has been reading Jimmy's book (Free Air by Sinclair Lewis) and that she plans to travel West like the main character. Jimmy realises that she wants to be an actress. He calls her pretty and she dodges the compliment. He insists, calling her prettier than Lillian Gish, and says he would watch her act.

Pearl attempts to joke about Jimmy saving her from her brutish father but he misses the reference to Gish's role in the film Broken Blossoms. Nevertheless, he plays along and Pearl says she might let him come with her to California. He says he would come and she says she thinks he needs taking care of. He laughs, kisses her and pushes her back onto the bed.

Capone meets with Greek speakeasy owner George Anastos while Jimmy watches from the bar. Anastos is concerned that Capone is pressuring him to buy alcohol from Torrio when he is currently supplied by Irish gangster Charlie Sheridan. Capone announces to the patrons that the speakeasy is in Torrio's territory. Anastos begs him to speak to Sheridan and says he is ignorant. Capone says that the Greeks are an intelligent people and asks the man to confirm that they invented arithmetic. Capone says Anastos should be able to predict the sequence of events before kicking him off his chair. Jimmy puts a hand on his gun, lets go and then approaches. Capone shouts down protests from a customer, offers to help the owner to his feet and then backhands him when he reaches up. Jimmy urges Capone to stop and Capone refuses. Capone tells the owner to make a big order when Torrio's truck comes around and threatens to destroy his stock if he does not. Finally he tells the owner to send Sheridan to the Four Deuces if he has a problem. He prompts Jimmy to follow as he leaves the speakeasy. The customers help the owner to his feet.

Back at the Four Deuces, Torrio admonishes Capone for causing problems. He says that he is happy for Capone to branch out as long as it is profitable for him. Capone promises to resolve the issue and plans to negotiate with Sheridan when he arrives. Torrio leaves, complaining about a planter's wart on his foot. Capone believes Torrio has left because he knows that Capone can handle the negotiation alone. Capone suspects that Jimmy is jealous of his progress and tells Jimmy that they will move up together. Jimmy says he is just passing through. Jimmy advises Capone to take over Sheridan's territory piece by piece and to negotiate for a portion now before expanding later. Capone greets Sheridan; Sheridan is annoyed that Torrio is not there. Jimmy gives Torrio's apologies and Capone says Sheridan should speak to him. Sheridan claims to be insulted and his enforcer, Liam, complains that the streetcars are not running. Jimmy offers refreshments and Sheridan refuses. Pearl enters and kisses Jimmy, telling him she is going to Chinatown. Capone asks after Anastos and Sheridan guesses that he is at the dentist. Capone says Anastos needs to learn some manners and Liam interjects that lots of people do. Capone rises to the subtle insult and Jimmy interrupts to explain the reason for the invitation and their desire to share territory in Greek Town. Sheridan says he is amused by the entitled attitude of New Yorkers. Capone points out that Jimmy is from New Jersey but Sheridan is disinterested. Capone tells Sheridan to stay out of Greek Town. Sheridan says they are already there and have been since James "Big Jim" Colosimo took over. Capone reminds Sheridan that Colosimo is dead and states that Torrio, a fellow New Yorker, is in charge now. Sheridan asks if there is room for negotiation and Capone invites an offer. Sheridan suggests 10% of their income and Capone demands 25%. When Sheridan accepts Capone senses weakness and tries to increase the split to 50%. Sheridan is initially incredulous but says he will accept to avoid trouble with Torrio and leaves. Capone calls Sheridan a loud mouth and claims he knew he would give in. Jimmy thinks Sheridan might have other plans.

Jimmy and Capone have a cup of tea while waiting to see a tailor. Both men are in their undershorts as they discuss Sheridan. Jimmy believes Sheridan presents a serious threat while Capone is dismissive. He generalises that Irishmen are loud but that this is driven by drinking. Capone suggests that he would afford more respect to a Sicilian rival. The tailor enters with trousers for both men. Jimmy thanks Capone for paying for the suits and Capone worries that the gesture might appear homosexual but says that they must look like businessmen. Capone notices the scarring on Jimmy's right leg and asks if it is from his war injury. Capone gestures to his own facial scarring and complains about the Germans. The tailor calls the slim cut "a la mode" and Capone looks to Jimmy to explain that it means current. The tailor notes the broad shoulders, designed for a masculine silhouette, and then asks for Capone's opinion. Capone says his wife "is gonna shit."

Liam returns to the Four Deuces while Jimmy and Al are gone. He sleeps with Pearl and then cuts her face with a knife. His men shoot the Bouncer and fire at the walls and ceiling to create a distraction for Liam to escape. Jimmy brings flowers for Pearl when he finds out but Regina (the Madam) tells him she is sleeping. Jimmy peaks through the door and sees that Pearl's face is covered by bloody bandages. Capone tells Jimmy to cheer up and points to his own facial scars.