In Chicago, Jimmy bonds with one of Johnny Torrio's prostitutes, Pearl, and finds himself increasingly at odds with the hot-headed Al Capone. Back in Atlantic City, Nucky looks to leverage his political relationships with ambitious U.S. Senator Walter Edge and Jersey City Mayor Frank Hague, while Eli and Chalky go to extremes to interrogate a local KKK leader.

Nucky tries to set up a risky liquor delivery to Philadelphia. Later, Attorney General Daugherty sees a problem that might complicate Nucky's case. Jimmy finds a new mentor in Leander Whitlock who is the Commodore's lawyer. Margaret finally goes to confessional. Lucy continues to struggle with loneliness while Van Alden tries to settle his conscience.

Undercut by Nucky, who has a new source for alcohol, Jimmy and his partners look to cultivate a new revenue stream in Atlantic City. With the peak tourist season approaching, the Commodore’s crew faces a choice in dealing with the city’s striking workers; either negotiate or fight back. Fearing that sin has led to misfortune, Margaret approaches Father Brennan with an “act of devotion.” Nucky gets a new lawyer. Van Alden faces an uncertain future. Manny Horvitz takes exception to a debt payment.

Disturbed by a recent nightmare and Billie’s absence, Nucky reluctantly joins Margaret to receive a high honor from the Church. Meanwhile, Gyp makes a deal with Nucky for a onetime liquor shipment, though the mobster’s longtime intentions remain very much up in the air. Van Alden regrets trying to socialize with his co-workers; Margaret takes her women’s-clinic pitch to a higher authority; Lucky and Meyer (Anatol Yusef) protect their investments; Richard sets the record straight with Mickey, and with Nucky.

Nucky tries to keep Jess Smith quiet and neutralize Gyp's alliance with Joe Masseria; Margaret considers an alternate future; Van Alden's side business backfires; Gyp's shipment is short; Chalky sees an opportunity.

Eli confronts Nucky after Willie makes an unpopular decision. Margaret has a surprise encounter at her job on Wall Street. Joe Masseria orders Lucky Luciano to return to Tampa and deal with Vincenzo Petrucelli. Gillian goes cold turkey, with Roy Phillips’ help. Still seething over his brother’s death, Al Capone tries to get Johnny Torrio to turn on rival gangster Dean O’Banion. As Chalky White and Daughter Maitland’s relationship deepens, Valentin Narcisse exerts his control over Dunn Purnsley and the Northside.

Federal agents enlist the help of Eli and Van Alden to take down the Capone organization.