Season 5 opens in 1931 with Nucky in Cuba, where he presses a U.S. senator on the likelihood of Prohibition's repeal and eyes a future business deal with a rum magnate. Meanwhile, Margaret witnesses a casualty of the Great Depression on Wall Street; Luciano makes a bold career move; Chalky catches a break to get out of a bad situation; and in a flashback to 1884, a young Nucky makes an impression on the Commodore.