Jack, Marcus, and Fogerty leave for Haines Falls. Jack says he went AWOL to see Paris, and suggests that he and Marcus go to Europe soon. Marcus also served in Paris during the war. They go to Mike Brady's Top O' the Mountain House and meet Charlie Northrup, a huge man with blond hair with whom Jack worked for a time in New York. Jack walks to a table where Murray "The Goose" Pucinski is sitting with Marion "Kiki" Roberts, an auburn-haired woman who Marcus thinks is the most beautiful woman he has ever seen. Kiki and Jack dance while Fogerty plays the piano. When Jack finally gives in and lets loose, kicking and swinging to the Charleston, Marcus thinks this must be how Jack got the nickname, "Legs."
Charlie behaves rudely to Jack, laughing at him and even spitting beer at him. This behavior shocks Marcus. He begins thinking about what happened to Joe Vignola. After the Hotsy Totsy incident, Vignola intended to tell the judge everything that happened. He was a good Catholic and wanted to show the thugs that crime did not pay. But Jack's men threatened Vignola so violently that Vignola finally went mad. He said that one night Jack came into his cell dressed as a Boy Scout and cut his brains out with a Boy Scout knife. Eventually, Vignola was sent to Bellevue, where he hid food under his bed to keep Legs Diamond away and scratched at the floor until his fingers bled. Finally, he was confined to a straightjacket. Filetti was acquitted and Jack never even went to trial. None of the fifteen witnesses would talk. Half a dozen underworld bosses decided that Jack was a loose cannon and they wanted him out of New York. He was told not to come back to the city. They go aerial bowling and miniature golfing. While golfing, Marcus admires Kiki's body and sneaks glances at her panties. Kiki uses sex as a weapon, which Jack appreciates just as he enjoys machine guns. Back at the hotel, Marcus overhears Jack and Kiki's conversation through the walls. Kiki is bored in Haines Falls with Goose. She wants to go to New York and marry Jack. Jack says that Alice is too depressed for him to divorce her right now, but that he will marry Kiki soon. Kiki says that she likes to kiss his scars.
Marcus ponders the similarities between Jack and the Great Gatsby. Jack's roadster is so similar to the one that Gatsby drove that Marcus thinks Jack bought it to emulate Gatsby. Jack knew Edward Fuller, the neighbor of F. Scott Fitzgerald's who was the basis for the fictional character Gatsby. Fitzgerald based his fictional character Meyer Wolfsheim on Fuller's partner, Rothstein, for whom Jack is working. Jack met Fitzgerald himself once on a boat to Europe.
On the way to the railroad station, Marcus tries talking with the Goose. He discovers that Goose met Jack in the army while both men were in jail. They got into a fight when a disagreement ensued after Jack tried to give Goose a glass of rainwater. Jack punched Goose in the eye so hard that he went blind in that eye. Six years later, Goose looked up Jack and Jack gave him a job. Halfway down the mountain, Goose hits the brakes and the car nearly slides off the road. Marcus gets out of the car and realizes that he is standing on the edge of a cliff. He gets back in the car and gets out on the other side. The car is stuck, but Goose picks it up and sets it straight.
For a period of time during Prohibition, gang-related violence was glamorized and mythologized. Figures such as Jack Diamond loomed large in the American imagination. The kind of hedonism and carnage Jack represented were glorified by many, perhaps in part because of a backlash against the senseless, puritanical repression of the temporary temperance laws. It might also be that America's participation in the Great War changed the nature of the country. Kennedy says that all three gangsters are war veterans. Perhaps the horrors they saw during the war numbed them to violence and made it easier for them to become violent criminals. Marcus was stationed in Paris during the war, and Jack went to Paris during a military stint. The Goose also served in the army.
When Marcus mentions Ichabod Crane and Rip Van Winkle, he associates Jack with old American legends of men who come from upstate New York. The idea of Jack as a character that has been created is further emphasized by his parallel relationship to the fictional character Jay Gatsby. Besides the familiar-looking roadster that Marcus feels Jack has bought for the very purpose of seeming like Gatsby, Jack and Gatsby are both are involved in the criminal underworld, have risen to wealth and fame from poverty and obscurity, and are wildly popular because of their wealth. Both men are lionized in tales told by a young male friend. Both young men are primarily attracted to the lifestyle of Jack and Jay. The Vignola story makes Jack's reputation as a man to be reckoned with, a brutal and relentless thug with the power to brutally trash a man's sanity. Vignola's hallucination about Jack dressed in a Boy Scout uniform is odd, considering that at this point, Jack is getting away with everything, and is the polar opposite of the virtuous Boy Scout ideal. He even manages to elude all criminal charges after the Hotsy Totsy episode.