On the season 5 premiere, Nucky makes business contact in Cuba, Chalky catches a break and Margaret watches the Great Depression take a casualty on Wall Street. 

The opening scene shows a young Nucky diving for coins with other boys off the Atlantic City pier as the Commodore kicks off the summer season in 1884. We then jump forward to Havana, Cuba in 1931 where Nucky and Sally await the arrival of a senator who gives Nucky some insight into the future of Volstead Act.

Back in New York, Margaret's boss addresses the office before shooting himself in the head. Later on she is questioned by the firm's head about the keys to her bosses's files. Margaret tries to pull the file on Arnold Rothstein without getting noticed.

Flashing back to Nucky's childhood we see his sister in bed ridden with illness. Nucky's father asks him what he has been up to and reminds him who he is after striking him.

Back to Cuba, Nucky witnesses some protesters in the street before noticing Meyer Lansky. Lansky says he is vacationing with his wife. The two men have not seen each other since Arnold Rothstein's funeral. When Nucky tells Meyer to say hello to Charlie for him, Meyer mentions that they don't speak that often. 

We catch up with Chalky who is in chains and wearing prison stripes. He is part of a prison work detail in the woods. Later on he and another prisoner escape following a riot with the guards and other prisoners.

Flashing back to Nucky's childhood we see how being honest when he returns a man's hat and money earns him a job with the Commodore.

Back in New York, Charlie meets with Joe Masseria who talks about the need for only one boss in the city. Charlie tells him he will take care of the competition, Salvatore Maranzano before excusing himself to go to the bathroom. When he does, a pair of men walk in and shoot Masseria.

In Cuba, Nucky meets with the head of the Bacardi rum family and tries to strike a deal to be their distributor in America when repeal is voted in. Later back at his hotel he avoids an attempt on his life thanks to his bodyguard. Later in the night he speaks with the woman he believed to be Lansky's wife, only to learn she was a local prostitute.

The episode ends with a young Nucky giving his mother his first dollar from the Commodore and then seeing his father crying over his ill sister. Nucky goes to bed reading a paper his mother found for him.