This story is about a young man, Joe Coughlin, who becomes a main leader in the illegal rum trade based out of Ybor during Prohibition. Joe Coughlin is both the son of a cop and an outlaw ("I'm an outlaw, not a gangster," he says multiple times). In the 1920s, he starts out as a small-time crook living in Boston and works independently alongside two childhood friends. The three of them don't work in the upper levels of organized crime; they mostly just rob and move a little bit of rum from place to place on the side. Joe Coughlin's relatively peaceful life changes when he makes the mistake of robbing a high-profile mobster named Albert White. White hosts backroom poker games in addition to dealing in rum, prostitution, and the drug trade. While robbing the poker game, Joe meets a woman named Emma. He falls for her immediately. Unfortunately for him, Emma is the girlfriend (or “moll”) of Albert White. Post-robbery, Joe tries to lay low for a while, to no avail. The owner of one of the hideouts Joe stays in dies. Albert White then goes to Joe to inform him that he and his friends can no longer work independently. Joe refuses and subsequently comes to blows with White and his associates. In addition to his refusal to play by White's mafia rules, Joe also is sleeping with White's moll, Emma. Joe senses coldness in Emma that intrigues and puzzles him. He wants to find out what made her the way she is. Joe's father, the police chief, meets Emma and says that Emma is dead inside and that dead part of her will never grow back. Joe and Albert continue to cross paths. One of Joe's childhood friends betrays Joe to White during a robbery and three cops chase Joe and his associates. Two of the cops die due to a car crash caused by the chase. Joe becomes a wanted man in Boston after that. He's in a very precarious position due to his father's profession as the police chief. After encountering no sympathy from his father, Joe goes to his father's home and steals clothes and a hat. He takes no money from his father's safe; he only leaves his dirty clothes atop the pile of money. The reason he needs the new clothes (a summer suit and a dressy hat) is because he is going to the casino that night. Emma and Joe have made plans to run away together. They plan to leave that night. Emma and Albert are at the casino and afterwards Albert is going away on a business trip. When Albert leaves, Emma and Joe will make their move. However, the deadness inside of Emma shows itself when, inexplicably, she betrays Joe to Albert. Albert catches up with him in the casino and brutally beats him. His men take Joe to their car, planning to kill him. They also take away Emma, whom Joe then brokenheartedly presumes to be dead.
Joe is saved by his father and his officers. However, his father is not the saving grace he appears to be. Furious over the earlier deaths of the two policemen, his father allows his officers to beat Joe mercilessly, putting him in the hospital. The ambulance driver remarks that Joe looks like he's been thrown off the roof of a building. Joe goes to the hospital and stays until he wakes from a coma. Remorseful at what he allowed his officers to do, Joe's father hires the best defense attorney he can find to plead Joe's case when it inevitably heads to trial for the murder of the two cops. Joe ends up getting five years in prison, a relatively light sentence. While in prison, Joe quickly becomes a target. He consistently and thoroughly fights off all of his attackers, save one. He is stabbed with a potato peeler and ends up in the hospital for three weeks. After he gets out of the hospital, he meets an old man named Maso Pescatore. Pescatore is a mob boss who operates an illegal rum trade along the eastern seaboard. He offers Joe protection in exchange for the cooperation of Joe's father in destroying the enemies of the Pescatore operation. Joe's father, bound by fatherly love, agrees to work for him. Though when Pescatore asks Joe's father to kill someone for him, he can't do it. Joe's father refuses and Pescatore threatens to murder Joe. Joe gives him his father's gold watch in exchange for mercy, but it's no use. That night, Joe gets a visit from two men who work for Albert White. They ask if Joe wants to work for them. Joe, seeing no other option, agrees. His first task is to kill Maso Pescatore. Joe devises a plan; he lures Maso up to the roof and threatens to throw him off. Joe lets Maso live because he needs to get some sort of revenge on Albert White. Maso and Joe, along with the assistance of some guards Maso bribed, together kill the men waiting at the bottom of the stairs for Joe to bring down Maso's dead body.
Joe's main motivation for working with Maso is to get revenge on Albert White for killing Emma. When both Joe's and Maso's sentences are up, Maso sends Joe down to Ybor to control the rum trade down there. Joe acquiesces and together he and a childhood friend work at consolidating the rum trade. They get cops, lawyers, and judges all in their pockets. In order to secure the help of a raw goods producer, they rob a naval ship for weapons. Assisting them in the robbery is a woman named Graciela. Not used to taking orders from a woman, Joe immediately clashes with Graciela. However, they manage to put aside their dislike for one another and successfully commandeer the naval ship.
Establishing the rum trade was hard, but keeping it going is even more difficult. Joe and Graciela end up teaming together and eventually falling in love. They deal with rival mobsters and KKK members who are trying to destroy Joe's organization for both racial and business reasons. During this time, Joe and Graciela fall in love and Graciela gets pregnant. She goes back down to her homeland of Cuba during the pregnancy while Joe stays in Ybor for business. While in Ybor, there is an unusual threat to Joe's organization. A female preacher and daughter of the Ybor police chief begins to speak out against drinking rum. Histrionic and passionate, she captures the enraptured attention of the crowd and business slows dramatically for Joe as people focus more on morality than drinking. Unwillingly to kill a female, Joe waits until she goes away of her own accord. The preacher does. She is a former heroin addict who has replaced one addiction (drugs) with another (religion). Unhappy with her life and her father, who is still mourning her deceased mother, she kills herself in her father's bed. Deeply saddened, her father blames Joe for her death.
Graciela has her child and business booms even further. Joe and Graciela's big house expands and the rum trade totals an $11 million a year growth (versus one million before Joe took it over). The relative peace soon ends when a New York gangster named Lucky Luciano steps onto the scene. Luciano is a friend of Maso Pescatore's and he wants only Italians in the top mafia spots (Joe is Irish). Furious with Maso, Joe speaks disrespectfully to him. Joe goes up to see Luciano, who tells him to agree to take a lower profit. Joe refuses. He valiantly defends his title as mob boss. Maso Pescatore, frustrated with Joe's noncooperation, meets with Joe. During the meeting, Maso orders Joe to be killed. But Joe is one step ahead of him—he already has shooters waiting to take out Maso. His shooters shoot Maso in the throat. Maso dies, but then Albert White walks onto the scene. Still holding a grudge against Joe, he and his men take Joe on a boat. They dunk Joe's feet into a cement bucket and then prepare to drown him with the weighty concrete attached to his feet. Joe saves his own life by telling Albert, Emma's former lover, that Emma is still alive. Joe knows Emma is still alive because he's seen a picture of her from a few days earlier. How she's alive, Joe can't imagine, but she is. Just as stunned as Joe is, Albert demands to know where Emma is. Joe won't tell him and they have a standoff. During the standoff, armed men from Joe's side storm the boat and kill all of Albert White's men. Albert White dies in the crossfire.
Joe manages to get back into Ybor. Finished with mafia life, he heads down to Cuba to be with his wife, Graciela. Graciela, Joe, and their son, Tomas, move into a former plantation house. The tobacco field outside their house is unplowed and unworked, but they hire people to put it back into business. Men, women, and children line up for employment at the fields. Joe builds the kids a baseball field so they have something to do in their free time. Tobacco makes a nice profit for Joe and his family, and they live in peace for a long time.
Joe does eventually find Emma. He sees her as he's walking down the street. He approaches her to talk. She looks hardened and bitter from life. She tells Joe that she never loved him. Joe walks away from her, realizing that his father was right when he said that deadness inside never really grows back.
Graciela is asked to attend an awards ceremony back in Ybor for all the work she's done rebuilding women's shelters and helping domestic violence victims. Joe convinces her to go back and receive the award. They fly into Ybor, but the second they get off the plane, bullets start flying. It's the preacher's father. He is still full of resentment at Joe for what he sees as Joe's culpability in his daughter's death. Graciela is shot and killed during the firefight. The book ends with Joe and his son together. Joe has become a more private person since the death of his wife. He stays in his home in Ybor. He takes his son fishing and often tells him stories of Cuba, pointing out into the horizon.
Best part of story, including ending:
I really liked this story because I've always been fascinated by the 1920s and I think the situation there with Prohibition is very similar to the one we have now with marijuana- cartels run rampant because the war on drugs has failed so badly. Also, I like main characters with flaws to them. Joe, though a criminal and an "outlaw," is actually a good guy. He may have killed and beaten people, but he also has another side to him, the side that builds baseball fields for kids.
Best scene in story:
My favorite scene was when Joe and the preacher talk to each other. She admits that the reason she picked up religion was so that she could replace one addiction with another. Her father is severely religious. It was my favorite scene because it opened up a new side of her. She wasn't the enemy of Joe, though they certainly didn't agree on a lot of things. This was yet another example of the many different facets Lehane puts into his characters.
Opinion about the main character:
I liked the fact that Joe was able to fall in love again. He said, earlier in the book after Emma died, that he would never be able to love another person. Throughout the book, we saw him grow and change as a person. He was able to find love again- a better love with Graciela, who doesn't have coldness like Emma does. I also liked Joe's lack of murderous impulses. He's a mobster, but he's no true killer. Maso even says that that's a main flaw in him. Joe isn't a killer.