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Main article: Chalky White

Chalky White remains a major character in the second season. This article details their actions in each episode of the season.

Chalky's warehouse is attacked by Klansmen, who shoot and kill four of his bootleggers; in retaliation, Chalky wounds two of them as they make an escape. Nucky orders the police to arrest Chalky for his own protection. While in prison, Chalky is moved to an all-black cell where he is taunted by an out-of-towner named Dunn Purnsley. Chalky does not respond, but instead marshalls the loyalty of his other cellmates so that they will beat Purnsley on his behalf.

After being bailed out, Chalky attends a meeting of black citizens whose gratefulness to him turns into anger when the subject of the murdered bootleggers is brought up. Nucky insists that Chalky restrain himself from seeking revenge for the time being, as Nucky is doing the same. He leaves, telling Chalky to "be a good boy... enjoy your family."

Season 2 reveals Chalky to have an upwardly mobile family, including a college-bound oldest daughter. He gives his consent to have an aspiring medical student court her. At the dinner where they are introduced to the boy, Chalky takes exception to his family and their guest mocking his "country ways." He gets angry and leaves them to entertain alone as he whittles.

The Age of Reason[]

Main article: The Age of Reason

Chalky attends a meeting chaired by Nucky Thompson in Nucky's suite at the Ritz Carlton hotel. Seated in the centre of the room are Chalky, alcohol importer Bill McCoy, New York crime boss Arnold Rothstein and Rothstein's Philadelphia connection Waxey Gordon. At the edge of the room are Nucky’s driver and enforcer Owen Sleater, Rothstein's protégé Lucky Luciano, Luciano's associate Meyer Lansky and Philadelphia gangster Herman Kaufman. With Atlantic City blockaded by the coast guard they are there to arrange delivery of McCoy’s shipments via Philadelphia. If the clear skies hold McCoy is planning to weigh anchor close to shore near Philadelphia at 2 a.m. the following night. Waxey explains that he will transport the liquor ashore in speedboats and has a dozen of them at his disposal. He estimates that this step can be completed in under an hour. Nucky and McCoy worry about the coast guard around Philadelphia and Rothstein confirms that Waxey has assured their safety. Waxey states that the guarantee of plain sailing is what he is being paid for. Nucky gripes about Waxey’s twenty percent share. Rothstein explains that once ashore the crates will be put onto trucks by Waxey’s men. Waxey points out Kaufman as the supervisor for this step and states that the trucks will be driven to the border of Atlantic City where Luciano and Lansky will complete the journey. Luciano complains to Rothstein that Waxey should earn his share by having his men complete the journey. Waxey compares Luciano to a woman asking to be walked home and Kaufman jokes about needing a good night kiss. Luciano threatens Kaufman and Lansky quiets Luciano. Chalky tells Luciano that he will expect delivery around 5 a.m. and reminds Luciano to signal his arrival with flashing headlights. Rothstein looks at Nucky and Nucky nods his assent.

The shipment is delivered as planned but not without incident. Jimmy Darmody attempts a hijacking but abandons the plan when he finds that Luciano and Lansky are the guards. The trio secretly make a bargain to work together to take control of the entire bootlegging operation from Nucky and Rothstein.

Peg of Old[]

Main article: Peg of Old

Nucky Thompson survives an assassination attempt at Babette's Supper Club. Nucky is shot in the hand and the assassin is killed by a federal agent before he can fire again.

Two Boats and a Lifeguard[]

Main article: Two Boats and a Lifeguard

Nucky Thompson invites Chalky to a meeting in his suite at the Ritz Carlton Hotel. Chalky begins by saying that Nucky wanted to see him and Nucky offers a drink. Chalky is indifferent to the type of spirit and Nucky selects a whiskey. Chalky wonders where Nucky’s drink is, Nucky jokes that his hand injury has cut his drinking in half before pouring one for himself. Nucky toasts to the future and Chalky wonders if he even has one. Nucky assumes that Chalky is worried about his upcoming murder trial and assures Chalky that he can beat the charges if he follows the advice of their attorney, Isaac Ginsburg. Chalky clarifies that he is worried about losing the support of the African American community because of their demands for justice after the warehouse shootings. Nucky says this justice is the subject that he wanted to discuss. Chalky wonders if Nucky is telling him to kill more Klansmen. Nucky says that Chalky is smarter than that and instructs him to exert his economic power by calling a strike. Chalky is concerned about such drastic action in the tourist season. Nucky explains that a strike will cost the city a fortune and empower Chalky in negotiations to end it. Chalky checks that Nucky is sure; Nucky reveals that he has given up control of the city in response. Eddie announces that the press are ready for Nucky’s announcement. Nucky announces that he will stand down as Atlantic County Treasurer and tells Jimmy Darmody that he plans to retire.

Battle of the Century[]

Main article: Battle of the Century

On July 1, 1921 Dunn Purnsley comes to see Chalky as he sharpens a knife in his garage. Chalky comments on Purnsley’s audacity on coming back to the garage on his own accord. Purnsley reminds Chalky that he told him they could talk any time, Chalky glares at him, and Purnsley removes his hat and adds the respectful address “Mr White.” Chalky snorts and reminds Purnsley of their fracas in prison. Purnsley says that they started badly and Chalky says that their current relationship is copacetic. Purnsley describes it as “sweet as Cracker Jack” referring to the popcorn brand. Purnsley describes Purnsley’s much improved situation since coming to Baltimore; a good job in a fine hotel, a gold tooth and plenty of cash. Purnsley agrees that things have turned out for the best and Chalky says that it is how he sees the world. Chalky asks for news and Purnsley relates progress seeding unrest among the kitchen staff. Chalky instructs Purnsley to bring things to a head. Purnsley succeeds in causing a strike the following day.

Georgia Peaches[]

Main article: Georgia Peaches

Purnsley is successful in triggering an ongoing citywide strike by African American workers. On July 24, 1921 strike breakers unsuccessfully attempt to break up the picket line Dunn Purnsley has arranged outside the Ritz Carlton Hotel. Lather that day Chalky and Purnsley meet with Jimmy Darmody and Richard Harrow in the Northside church where Chalky attends community meetings. The meeting is under the guard of two armed men in opposite corners of the hall. Chalky greets Jimmy as “young James” and shakes his hand. Chalky wonders how Nucky Thompson’s shoes are fitting and Jimmy says they are tighter than expected, gesturing at the room and referencing the strike. Chalky says that they need to be broken in. Chalky asks the reason for the meeting and Jimmy answers that he is there to negotiate an end to the strike. Chalky laughs at the timing and asks Purnsley’s opinion. Purnsley deadpans that Jimmy’s ball team of strike breakers have struck out. Jimmy says that the strike breakers were not his idea. Chalky brings up the Ku Klux Klan attack on his warehouse and Jimmy denies involvement in planning that too. Chalky sarcastically wonders if Jimmy has any ideas of his own. Jimmy responds with an offer to have the murder charges against Chalky dismissed. Chalky wonders how he will achieve this and Jimmy reveals that he has influence with Governor Edwards. Chalky looks round at Purnsley and then asks what else Jimmy can offer. Jimmy wonders what Chalky wants from him and Chalky asks for justice, explaining that he wants $3000 for each of the families of his men who were killed. Jimmy agrees to this and Chalky goes on to say he wants the three remaining Klan members responsible delivered to him personally. Jimmy balks at this and looks at Harrow. He tells Chalky that it is not possible and Chalky stands up and says that there will always be next tourist season.

To the Lost[]

Main article: To the Lost

Jimmy Darmody attempts to make amends for his betrayal of Nucky Thompson, despite knowing that Nucky will never forgive him. He is aided by Richard Harrow. They kidnap the three remaining Ku Klux Klan members responsible for the raid on Chalky's warehouse.

Three African American men with shotguns guard Chalky’s warehouse at night. Two trucks drive down the road towards the warehouse. Dunn Purnsley and Chalky are waiting inside. A man watching the door announces the arrival of the cars. Chalky tells him to open up and he slides the main doors apart. Jimmy drives the lead vehicle into the warehouse. The gunmen stop Harrow (in the following car) outside. Jimmy exits his truck and hands Chalky a stack of cash in a burlap sack. He explains that it contains $20,000, $5,000 for the family of each murdered man. Chalky points out that he only asked for $3,000 each and Jimmy says that he was aware. He pulls the cover from the flatbed revealing three Klansmen, bound and gagged. Nucky asks if Jimmy is sure and Jimmy says that they can ask them if they like. Purnsley says that it will be his pleasure and unfolds his switchblade. Chalky notes that the governor’s office has dropped his case and says that Jimmy can tell The Commodore that he will end the strike. Jimmy says that he will, avoiding giving away The Commodore’s death. Jimmy asks Chalky to pass a message to Nucky; he is ready to talk. Chalky nods assent and Jimmy walks back to Harrow’s car. Chalky welcomes the Klansman back to the scene of their crime. His men pull two of them out of the truck and beat them with clubs. Purnsley crawls up onto the flatbed with his blade in hand and a smile on his face. Later, Chalky calls Nucky to broker a meeting with Jimmy.

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