It is 1975, and Marcus Gorman, a real-life Albany lawyer who once defended the infamous New York gangster Jack Diamond, meets with some old friends: Packy Delaney, a bar-owner, Flossie, a whore, and Tipper Kelley, a newsman. The group is at the Kenmore Hotel, swapping memories of Jack. Marcus narrates the novel, which is composed of stories he has pieced together about Jack.
Marcus meets Jack and his brother, Eddie, in 1925. They are at the Kenmore, and Marcus butts into a conversation they are having about Al Jolson. Five years later, Jack invites Marcus to lunch and asks Marcus to be his lawyer. Joe "Speed" Fogarty, Jack's right-hand man and driver, picks up Marcus and takes him to Jimmy Biondo's farm in East Durham, which Jack rents and uses to store illegal booze. There Marcus meets Jack's wife, Alice, and the three of them take turns firing machine guns in the barn turned booze storage space. Afterward, they drive to Jack's farmhouse in Acra. Jack and Alice get in a fight over their canaries when Alice discovers that Jack calls one of them "Marion" after a girl he has been seeing on the side. Fogarty, Jack, and Marcus leave and drive to Haines Falls in the Catskills to a place called The Top O' the Mountain House. There, Jack and Charlie Northrup, another prominent local gangster, get into a fight. Marcus also meets Marion "Kiki" Roberts, a Broadway dancer, whom Jack has been keeping at The Top O' the Mountain under the supervision of his small-minded, one-eyed strongman, The Goose. They all go aerial bowling and miniature golfing, and Marcus admires Kiki's physique. Later, Marcus overhears a conversation between Jack and Kiki in which Kiki sounds annoyed at being cooped up and frustrated that Jack will not dump Alice and marry her instead.
Marcus accompanies Jack on a drug-run to Europe. Shortly after they leave, the news reaches their boat that Charlie Northrup's bloodstained car has been found in Brooklyn with one of Jack's men. Suddenly Jack and his entourage are the stars of the ship. Jack has a fling with a librarian, but soon dumps her. Before they reach Europe, the librarian tries to kill herself but does not succeed. As news of the unsuccessful search for Northrup's body reaches the ship, tension mounts. They receive word that Biondo, who has supplied the funds for the heroin deal, wants to back out. But Jack presses on and gives the money to Marcus to hide. Jack also wants Marcus to carry his jewels, but Marcus refuses, so Jack dumps them overboard. Marcus has a one-night stand with a woman whose name he does not remember. When the ship reaches Europe, the press mobs Jack. Jack is turned away from Britain and Belgium, and detained in Germany. In Germany, Marcus finds Jack a local lawyer. They meet the lawyer for lunch, and the lawyer brings along his nephew, a semi-famous playwright named Weissberg who writes about small-time crooks. Weissberg tells Jack that he wants to follow him back to the States, observe him, and write a play about him. Jack shoots a pistol between Weissberg's feet and tells him he's just a stupid kid. Jack takes a freighter back to America. There are forty-five hundred canaries on board, and Jack is the only human passenger. Although the canaries are afraid of Jack at first, he makes friends with the birds and takes three of them home with him.
Biondo starts threatening Marcus and Kiki, demanding that Jack return his money, which Jack never does. Marcus learns that Northrup visited Jack one night. Jack was angry because Northrup had tipped off federal agents about one of Jack's rum boats, so Jack proposed a partnership as a means of allowing Northrup to pay him back. Northrup refused, and Jack had his men beat him up. When Northrup fought back, The Goose shot and killed him. Jack had The Goose burn his body. Late in 1930, The Goose is ambushed at a bar and shot six times, but he does not die.
Jack is shot five times at a hotel while Kiki is in the shower, but he survives. While he recovers, Jack keeps Kiki out of sight, and Alice takes care of him. She puts a crucifix over his bed and turns away the press when they ask her about Kiki. Marcus starts trying to bribe Upstate politicians for Jack, unsuccessfully. Alice has a "Mormon" dream, about Jack bringing home another wife. Marcus brings a Broadway producer named Lew Edwards to see Jack and Alice at their home. The producer suggests that Jack pretend to have found religion, and start a preaching routine that they could take on tour around the country. The producer suggests that the nation would eat up the idea of one of its most notorious figures having a change of heart inspired by God. Jack thinks the idea is hypocritical. Alice finds out that Jack has been staying in touch with Kiki, and she leaves him.
Kiki moves in with Jack, but is frustrated by his low sex drive. They sleep in separate rooms. One night Kiki walks into Jack's room, naked, to surprise him. She strokes his chin, and he wakes suddenly, holding a gun to her face and bending her fingers backward. Earlier that same night, they had run into a local bumpkin, Clem Streeter, moving some hard cider. Jack kidnapped him and his companion, a boy named Dickie Bartlett, and took them back to his farm. There, he burned Streeter's foot and nearly hanged him, trying to get him to say where his still was. Streeter claimed he knew of no still. Finally, Jack let him go, largely because Fogarty urged him to do so. Jack is arrested, but is soon out on bail. Fogarty comes out of hiding to tell Jack that The Goose is looking for him. While they are at a bar, Jack is ambushed by two drive-by shooters, who hit him with four shotgun pellets. Fogarty gets him to the hospital, but then Fogarty is picked up by the cops. Marcus refuses to take on Fogarty as a client, because Fogarty does not have the money to pay him. Jack moves into a suite at the Kenmore with both Alice and Kiki. Alice and Kiki live in harmony and enjoy going shopping together. However, both of them have secretly enlisted the help of voodoo specialists to hex the other. Marcus goes out to dinner with them, and all night Alice and Kiki wonder who Jack will ask to dance first. Finally, Jack asks Kiki to take his left (now paralyzed) arm, and Alice to take his right arm, and they all dance together.
Jack goes through two trials. He wins the one in Troy, but loses the federal trial in Manhattan and is sentenced to four years in jail. He takes back the Biondo-money from Marcus and tries to form a new gang, but that gang is soon busted up. Marcus joins Jack on a beer run, which ends at Packy Delaney's Parody Club. Flossie is there, and they drink and sing until it is reported that The Goose is parked across the street. They call the cops and hide out upstairs until the cops come to take Goose away. Left alone for a moment, Marcus and Flossie have sex on the floor while a huge rat with red eyes watches them. After Jack is acquitted at his second Troy Streeter trial, he has a party at The Parody with fifty of his closest friends. Kiki is not there out of respect for Alice's feelings. After a while, Jack leaves to go see Kiki. After he and Kiki have sex, Jack goes home to his Albany apartment. That night he is murdered by two gunmen who shoot him three times in the head. Kiki and Alice both use their notoriety as Jack's women to create traveling stage shows. Kiki's show lasts longer, and Alice ends up hanging around Coney Island. She is murdered not too much later. The last time Marcus sees Kiki, she is performing in a strip tease show. She soon fades from the spotlight.