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.

After his father Ethan is injured in a fall, Nucky uses the opportunity to refurbish his childhood home. On a double-date with new friend Annabelle and her beaux, Margaret tries to get Nucky to open up about some painful childhood memories. During a visit to an army hospital, Jimmy befriends disfigured vet Richard Harrow, whose sharp eye proves invaluable. Van Alden gets a lead on the woods massacre.

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.

Nucky is forced to readjust his political alliances with a Democratic mayoral candidate promising to wipe out corruption. Jimmy returns from Chicago to deal with the D'Alessio gang, which has allied with Rothstein to import European scotch through Atlantic City, but is arrested by Agent Van Alden for the massacre in the woods. Margaret intercedes with Nucky on Madame Jeunet's behalf, while Angela finds her romantic and artistic ambitions halted by Jimmy's return.

Nucky asks for Margaret's assistance in backing his mayoral candidate with the passage of women's right to vote, leaving her conflicted about her role. Doyle switches sides back from Rothstein, which leads Nucky to conspire with Chalky against Lansky and the D'Alessios. Angela witnesses Jimmy's violent side against her photographer friend, and considers leaving Atlantic City for good in the aftermath. Van Alden grapples with his emotions, and has encounters with both Margaret and Lucy.