Marcus Gorman leads a pretty dull life until he meets Jack Diamond. In fact, Marcus decides to take on Jack as a client just after realizes how much his life could use excitement. Not particularly interested in putting his own life in danger (Marcus refuses to smuggle jewels for Jack and becomes nervous when Jack informs him that he is taking Marcus along for a beer run), Marcus feels a vicarious thrill when he hangs out with Jack, one of the country's most notorious gangsters. Marcus loves shooting Jack's machine gun, enchanted by the gun's lethal power. He loves looking at Jack's wife and girlfriend. Eventually, he seduces and sleeps with anonymous women, just as Jack does. Marcus gets a homoerotic thrill from Jack, too. Jack's immense energy attracts those around him. Kiki experiences a certain amount of sexual satisfaction just by hanging around Jack. She relishes the attention she gets just for being Jack's sex object. Being Jack's girlfriend makes Kiki more famous than her dancing ability ever could. Both Marcus and Kiki are so drawn to Jack's villainy that even if they consider leaving him, they always come back to him in the end. Kiki nearly witnesses Jack's bloody demise, but remains true. Marcus hears gruesome stories of Jack's violent mob tactics, but does not leave him. Alice, despite her disapproval of Jack, enjoys some of his villainous glow. The fact that everyone stays with Jack shows how thrilling it is to be near him and to soak up his badness.
In one sense, Jack embodies the man who has achieved the American Dream. Like F. Scott Fitzgerald's Gatsby, Jack comes from nothing and becomes a rich, successful man. Like the protagonist of a Horatio Alger novel, he succeeds against the odds, climbing to fame and riches from the bottom of the Philadelphia slums. However, Jack is compared not just to Gatsby and an Alger creation, but to Ichabod Crane and Rip Van Winkle, fictional American legends from upstate New York. Kennedy is suggesting that if Jack partially achieved the American Dream, he is also partially a legend, a fictional creation—and not just in this novel, which is a fictional memoir. The real man, Jack "Legs" Diamond, was mythologized and even created by the men who wrote and talked about him. The press wrote of his success, lies and tall tales built on it, and Jack himself spread the word of his own fulfillment of the American Dream. Jack's achievement of the American Dream is partly a fact, and partly a fiction created by a variety of authors.
Jack has had a special affection for cats since he and Eddie adopted Sugarpuss as boys in Philadelphia. Marcus notices the similarities between Jack and his cat, Pistol, when he first visits Jack at his farm. Jack and Pistol move with the same quickness, and Pistol hunts his prey with the same control with which Jack hunts his human prey. And like cats, which are said to have nine lives, Jack has an uncanny ability to elude death.
The rosary Jack carries from time to time signifies his guilt over losing touch with his family and his religion. Jack sings a song called "My Mother's Rosary," which likely suggests the guilt he feels upon thinking of his mother and her faith. Jack has tried to make up for his wicked lifestyle by donating gobs of money to his local church. He probably feels guilt beyond the guilt caused by living a sinful life, for he has also abandoned his faith and joined the Masons, a Protestant group. Jack claims to have joined the Masons for business purposes, but he is genuinely interested in the organization.
Jack develops a special fondness for canaries, mostly due to his odd experience on a canary-carrying freight boat. Jack can relate to canaries in many ways. A reporter once calls Jack a bird in a gilded cage. Jack is like a caged bird because he is tied to a lifestyle that places certain restrictions on the way he must conduct himself. Alice and Kiki are also connected to canaries, because Jack names his two canaries after his two women. Kiki has a lot in common with a caged bird, for she is constantly kept in a hotel under the supervision of one of Jack's men. At one point, Kiki tells Jack that he treats women like animals. He does force Alice and Kiki to live with him almost as if they are pets he is collecting.
The fudge that Kiki makes for Jack symbolizes her temporary futility and Jack's impotence. In contrast to Alice, Kiki cannot do anything in the homemaking realm. Her purpose, for Jack, is sex. When she makes fudge, however, she proves utterly futile, as far as Jack is concerned. Not only does she fail in the homemaking realm—the fudge will not harden—she fails in the sexual realm by failing to turn Jack on. Kiki and Jack go through this night without having intercourse because Jack cannot get an erection.
The first thrill Marcus experiences during his association with Jack is getting to handle a submachine gun (a "Tommy"), a symbol of the gangster era. When Marcus holds the gun, he is reluctant about its lethal power, thinking about the commandment "thou shalt not kill." But Marcus gets over his fear, and after he shoots a few rounds, he turns out to be a good shot and enjoys the thrill of handling the weapon.
Jack puts up an all-seeing Masonic eye that Jack puts up in his bathroom, symbolizing his rejection of his Catholic background. Alice cannot stand the eye or Jack's involvement with the Masons. She decorates the house with crucifixes and holy pictures, so Jack gets under her skin by hanging up his own religious symbol.