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 visits Chicago for the Republican National Convention, where he finds himself intrigued by the candidacy of Warren G. Harding over more established candidates. The D'Alessio gang moves in on Nucky's territory at the expense of Eli, who has been watching over his brother's affairs. Margaret finds herself entangled in Nucky's business affairs, while Van Alden struggles with his wife's desire for a child. Rothstein prepares for legal trouble over his role in fixing the 1919 World Series. Nucky asks Jimmy to return to Atlantic City to reinforce his position.

Rothstein vents to Nucky and delivers a message to Gyp. Gaston Means sees an opportunity. Billie gets a new co-start. Van Alden and Sigrid receive an unexpected visitor. Gillian worries about her business.