Summary: Chapter 5: Playing the Jack Gentleman

Right before Marcus and Jack arrive at the Monticello, Jimmy Biondo visited Kiki. Kiki relates the stories Biondo told her: about Joe Rock, for example, who owed Jack money. When Joe wouldn't pay up, The Goose masturbated into a cloth and then rubbed the cloth in Rock's eyes. The Goose had syphilis and the clap, and Joe went blind. Biondo also told Kiki about the time Jack set fire to Red Moran's car while Red was still in it. Red's girlfriend knew about the burning, so Jack killed her and dumped her in the river. Jack leaves and tells Marcus to take Kiki out to dinner. Kiki is frustrated about Jack always leaving her, and thinks she cannot stay with Jack if he has really done the things Biondo says he did. Biondo's stories make Marcus reconsider his affiliation with Jack, too. That night, one of Biondo's close friends is shot four times in the head.

The next day, Jesse Franklin calls Marcus and tells him that once, at Biondo's farm, he went into the barn and stumbled upon something wrapped up in canvas. It was a human head, black and blue and beaten up, and other chopped-up body parts. Fogerty tells Marcus how Northrup died. Northrup had tipped off the feds about Jack's rum-boat. When Jack found out, he had Goose and Ox beat him up. Fogerty, Jack, and Kiki went out for dinner. When they came back, Oxie told Jack that Northrup had been shot when he untied himself and attacked Goose with a tire iron.

Marcus goes to visit Kiki in New York, and she talks about how much she enjoys being the center of attention because she is with Jack. She loves being touched and looked at as a sex symbol. On October 11, 1930, three men from Vincent Coll's gang shoot The Goose six times. Later that night, Biondo visits Jack. The men quarrel about money that Jack owes Biondo. Biondo leaves. On his way out, a drive-by shooter kills two of his men.

Kiki begins to realize that Jack will die a young man, which makes her want him more. Yet her conscience plagues her and tells her not to stay involved with him. Buying a newspaper one day, Kiki encounters a man with a gray bowler hat and a blond walrus mustache who tells her that she should be in show business because it is the only place for talentless beauty. Kiki is offended and says that she was about to leave show business. The man says that is a mistake, and says she looks like a bird wounded in the heart. He gives her a card. Kiki tells him that she is Jack Diamond's girl, and the man takes back his card and says she will not need his help. The man packs up his things and scurries off.

The newspaper headline says that Jack Diamond was shot five times in a 64th Street hotel. Kiki was there. She was in the shower when she heard the shots, and came out to find Jack gurgling blood. Kiki goes to her friend Madge's place, and hides in a closet when cops come to the door. They search the house and find Kiki. The next day Jack and Kiki are even more famous. Kiki publishes her memoirs in the News.

Jack recovers at the Polyclinic Hospital. Although he never reveals the identity of the shooters, Marcus says that they were neutral underworld figures sent to retrieve Charlie Lucky's money. Owney Madden ends up paying Jack's hospital bill in cash. Jack asks Marcus to draw up his will, leaving a mere $10,000 to Kiki and everything else to Alice. Alice spends a lot of time comforting Jack during his recovery in the hospital. Jack's left arm is paralyzed, but he is more popular than ever. Many people write to him. In one letter, a woman asks him to drown her six kittens for her; she cannot afford to feed them, but does not have the heart for murder. Jack asks Marcus to talk to Upstate politicians and see what they think of his operations. Marcus visits an old friend, Warren Van Deusen, a Republican county politician. Marcus asks him what the town folk think of Jack. Van Deusen says they think he is a hero, but the kind of hero that they wish lived elsewhere.

Analysis: Chapter 5: Playing the Jack Gentleman

Gruesome stories and tall tales of Jack's gangster exploits fill this section. The stories of Goose spreading his venereal diseases at Jack's request, the murder of an underworld figure's innocent girlfriend, and the desecration of Northrup's body point to a purely evil side of Jack's persona that is not immediately obvious from his behavior. The stories begin to make Marcus nervous, and he considers quitting. Marcus enjoys the excitement of hanging out with gangsters, but the thought of violence makes him nervous.

The stories also make Kiki reconsider her involvement with Jack. She has ample motive to leave him, from the tales of his nefarious doings, to his habit of leaving her under guarded supervision, to hearing him get shot from the shower. But Kiki is also attracted to the violence that makes Marcus repellent. Jack's badness turns her on. She loves him more when she realizes that he will die a young man. Kiki also relishes the secondhand attention people lavish on her when she is in Jack's presence. The strange street man who gives Kiki advice takes back his card when he finds out her affiliation with Jack. Kiki is not above capitalizing from Jack's accident, and uses it as an opportunity to publish her memoirs in the paper.

Despite the horrifying revelations that pepper this section, neither Kiki nor Marcus nor Alice leave Jack. The inability of any of these characters to tear themselves away from Jack illustrates the powerful magnetism of Jack's presence. Even the townspeople of Catskill feel similarly torn about Jack, relishing the "hero" in their neighborhood while nervously shying away from his reputation for violence.