Live by Night

The novel opens with a flash-forward: Joe Coughlin stands on a tugboat in the Gulf of Mexico with his feet encased in cement, twelve gunmen waiting to throw him overboard. He reflects that nearly everything significant in his life began the morning he first crossed paths with Emma Gould.

In 1926 Boston, Joe is a nineteen-year-old petty criminal and the youngest son of Thomas Coughlin, a powerful police officer soon to be promoted to deputy superintendent. Joe robs an illegal gaming room in South Boston alongside his partners, the brothers Dion and Paolo Bartolo, expecting an easy job. Their boss, Tim Hickey, had assured them the place belonged to harmless Greeks, but they find armed men at a poker table, including Brendan "Brenny" Loomis, a killer who works for Albert White, the city's most dangerous gangster. During the robbery, Joe encounters Emma Gould, a young woman serving drinks, and is captivated by her composure and beauty. Joe wisely avoids robbing a padlocked counting room, preventing open war with Albert White, and the trio escapes. Joe soon learns Emma is Albert's girlfriend.

Despite the danger, Joe tracks Emma to a hidden speakeasy in Charlestown and begins a passionate, secret affair with her, even as she continues seeing Albert. Joe's infatuation deepens into what he believes is love, but Emma remains emotionally guarded and refuses to say she loves him. Joe's relationship with his father is strained: Thomas, pragmatic and corrupt in his own way, dismisses Emma as "dead inside" at an awkward dinner and pressures Joe about his criminal life.

Tim Hickey is assassinated, and Albert White seizes his territory, offering Joe a stark choice: join his organization or leave Boston. Joe and Emma hatch a plan to flee to the Gulf Coast using proceeds from a bank robbery in Pittsfield, Massachusetts. The robbery goes catastrophically wrong. Joe, distracted, reverses the getaway car into a lamppost. During the pursuit, two police officers die in a burning cruiser and a third is shot dead, likely by Dion. Joe escapes with $62,000 stashed in a bus station locker and heads to the Hotel Statler to find Emma at Albert's grand opening gala.

In a service elevator, Joe gives Emma the locker key and she tells him she might love him. In the basement, Brenny Loomis ambushes Joe, and Albert White appears: Emma led Joe into the trap. She begs Albert to honor his promise not to kill Joe. As Albert's enforcer Donnie Gishler drags her to the elevator, she screams that she loves Joe. Thomas arrives with police, spits in his bloodied son's face, and turns him over to officers who beat Joe into a coma. Gishler flees with Emma; police chase them to Marblehead, where the car plunges into the sea. Gishler is found dead, but Emma's body is never recovered. Paolo Bartolo is killed during the wider manhunt. The public scandal over Joe's beating leads to Thomas's demotion, but Thomas leverages blackmail to secure Joe a plea deal of five years and four months.

Joe enters Charlestown Penitentiary in the summer of 1927. After being attacked by multiple inmates, he is taken under the protection of Tommaso "Maso" Pescatore, an elderly crime boss running his empire from behind the walls. Maso uses Joe as a conduit to Thomas, passing addresses of rival operations for Thomas to raid. When Emil Lawson, a violent lifer working for Albert White, forces Joe into a conspiracy to assassinate Maso, Joe instead betrays Lawson, warns Maso of the ambush, and pledges loyalty to the Pescatore Family. Thomas dies of a heart attack during Joe's incarceration. Joe's eldest brother, Danny, an estranged former cop now working in the film industry, offers Joe a new life in California, but Joe declines.

After his release, Maso offers Joe the position of running his West Florida operations in Tampa. Joe arrives in August 1929 and reunites with Dion. He meets Esteban Suarez and his sister Ivelia, who control the molasses and rum supply from Cuba. The Suarezes agree to deal directly with Joe on one condition: he must steal weapons from a U.S. Navy transport ship to arm Cuban revolutionaries against the Machado regime, the authoritarian government of Cuba. Joe is directed to Graciela Corrales, a cigar roller and fervent revolutionary. She is married to a man she believes is a political prisoner in Cuba, though Esteban tells Joe the husband is a con man who has been free for two years.

Joe executes an audacious two-phase plan: a bomb sinks the navy ship, forcing the weapons ashore, then Joe's men, disguised in National Guard uniforms, seize the crates from an armory. During the operation, Joe kills a sailor to save Graciela, crossing the threshold from outlaw to gangster. The weapons are shipped to Cuba.

Joe confronts Dion, who confesses that he, not Paolo, sold Joe out to Albert White before the Pittsfield robbery. Joe spares Dion and lies to Maso, blaming the deceased Paolo. He establishes boundaries with Tampa's incorruptible police chief, Irving Figgis, then confronts Albert White at a café and drives him out of Tampa. Joe and Graciela begin a passionate relationship, and their business empire grows to net over eleven million dollars a year. Joe acquires a seaplane piloted by the eccentric Farruco Diaz, buys up properties throughout Ybor City, a multiethnic neighborhood built around the cigar industry, and converts failed businesses into speakeasies, a school, and a free clinic.

RD Pruitt, a volatile Klan member and Figgis's brother-in-law, terrorizes Joe's operations. Joe coerces Figgis into arranging a meeting by showing him photographs of his daughter Loretta, who fell into heroin addiction and prostitution in Los Angeles. At the meeting, RD stabs Joe in the abdomen, but Dion and Sal Urso, Joe's trusted bodyguard, execute RD from a hidden position above. Joe survives after four surgeries; his father's Patek Philippe pocket watch deflects the knife's path. During his recovery, Joe and Graciela exchange private marriage vows.

Joe pursues legalizing gambling in Florida, but Loretta Figgis returns to Tampa as a hugely popular Pentecostal preacher whose influence torpedoes his casino plans. After confessing to Joe that she no longer believes in God, Loretta kills herself. That same evening, Joe discovers a photograph proving Emma Gould is alive in Havana.

Graciela tells Joe she is pregnant just before Maso arrives to strip Joe of power, announcing that Lucky Luciano has decreed only Italians can hold top positions. Maso orders Joe to kill Dion, having learned from Albert White that Dion was the real informant. Joe refuses. Maso's forces hang two of Joe's men from the hotel. Albert, now allied with Maso, places Joe's feet in cement on the tugboat, fulfilling the opening scene. Joe buys time by showing Albert the photograph of Emma alive. Farruco Diaz's seaplane swoops in with Dion manning the machine gun, and two runabouts close from different directions. Albert and Maso's men are killed. Joe recovers his father's watch from Albert's vest, then enters Maso's hotel suite, having turned Maso's bodyguard Seppe Carbone to his side, and shoots the old man dead. Dion kills Maso's son Digger.

In New York, Joe proposes to Lucky Luciano that Dion serve as the new boss, satisfying the Italians-only rule, while Joe acts as consigliere. Luciano agrees and introduces Joe to Meyer Lansky, who shares Joe's vision for casinos in Florida and Cuba.

Joe and Graciela relocate to Cuba, where their son Tomas is born. Joe purchases a bankrupt tobacco plantation, hiring foreman Ilario Bacigalupi, known as Ciggy, to resurrect the farm. In late spring 1935, Joe visits Emma at her brothel in Old Havana. She reveals she shot Gishler, swam free from the sinking car, and stole Joe's bus locker money. She offers him freedom. Joe declines without regret and walks away.

When the family returns to Tampa for an award ceremony, former chief Irving Figgis, consumed by grief over Loretta's death, ambushes them at the port terminal, chanting "Repent." Figgis kills Seppe Carbone and mortally wounds another bodyguard. A bullet passes through Joe's raincoat and strikes Graciela. Figgis steps into the path of a coal truck and is killed. Joe holds Graciela as she dies, her last words a declaration that she always loved him.

The novel closes with a brief coda set years later. Joe remains a respected but remote figure in Ybor, described as "pleasant" where he had once been "pleasant and surprisingly open." He ages quickly and walks with hesitancy. Sometimes he takes Tomas fishing at sunset on the seawall, putting his arm around the boy and pointing toward Cuba.