Four days after his visit to the mountain, Jack goes with Fogarty to see Marcus in Albany. Jack gives him five hundred dollars cash as a retainer and tells Marcus that he wants to go to Europe with him. The next day, Marcus is woken up at three in the morning by a phone call from Jack, who says that they have to leave for Europe that day. Marcus goes. Marcus and Jack, along with Count Duschene, Jack's international associate who speaks four languages, and Classy Willie Green, a card thief whom Biondo had hired to represent him, are taking the Belgenland to Plymouth and Brussels. The purpose of the trip is to buy heroin in Frankfurt, Germany and then go to Paris for vacation. Two days out to sea, the men hear that Charlie Northrup's bloodstained car was found in a garage in Brooklyn. Oxie was arrested in his apartment with an arsenal of guns, gas grenades, ammunition, and explosives. The same day a fox terrier jumps overboard, apparently committing suicide. After people find out about Northrup, Jack and his companions are the stars of the boat. People crowd around Jack.
Marcus asks Jack about Ox and what he knows about Northrup, but Jack gets defensive. Marcus says he does not want to be involved with upstate New York's biggest murder case in years. Jack storms off and the men don't speak to one another for two days. Jack takes up with a librarian from Minneapolis. One day, Jack says she wanted his signature on her panties. Later, the librarian comes up to Jack and says, "you turn women into swine." The radio reports that the search for Northrup is one of the biggest in New York state history. Classy Willie calls a meeting in Jack's cabin and says that Biondo wants to call off the deal. He wants Jack to give Willie the money, which Jack refuses to do. Jack says that he has eighty thousand dollars in jewels he needs to get off the boat somehow. Marcus refuses to carry them.
When they reach Plymouth, the British press mobs Jack. Stories in the papers fabricate outrageous tall tales of his notorious deeds. Jack tells them that he's not a gangster, just a bootlegger. At a press conference, one reporter asks Jack about his Knight Templar lapel pin. It turns out that Northrup was the one who got Jack into the Masons. One night when they were playing cards, Northrup told Jack that the suit "jack" meant a knave among kings and queens. Jack liked the idea, so Charlie told him more about the Masons and their symbols, and eventually proposed him as a candidate in his order.
Jack has a string of bad luck. A rash covers his hands. Another passenger shoots off three of his toes playing skeet and says Jack had hexed the weapon. The librarian cuts her wrists, although she then calls for help. One night, Marcus finds Jack on deck fingering a rosary. The British authorities decide that they will not let Jack into their country. Jack wants to get rid of the jewels and tosses them overboard. Jack says the boat is a jinx. Marcus confronts Jack about Northrup again, and Jack says that he thinks he is dead. Jack tells Marcus about his first murder. One night Rothstein told him to get a haircut and made him feel like a bum. Later, when someone named Wilson tried to cheat at cards, Rothstein told Jack to take him away. Jack took him to the river. Wilson offered him four grand to let him go. Jack took the money, shot Wilson three times, and dumped him in the river. With the money, Jack bought a new suit and a haircut at the Waldorf-Astoria.
Shortly thereafter, Jack and Eddie met Ace O'Hagan, who drove for Big Bill Dwyer. One night Jack stuck a pistol in O'Hagan's ear and insisted that he take them to a booze drop-off, smashing in O'Hagan's nose when he resisted. O'Hagan did so, and helped them load the truck with Scotch and champagne. Jack took O'Hagan to the hospital to fix up his nose, sold the booze to Rothstein, and asked for two more trucks to make more runs. Soon after, he was hit by a drive-by shotgun assailant while in his car. Bleeding profusely, he managed to drive to the hospital. His assailants were members of the "guinea mob" and O'Hagan, whom Jack murdered after extorting the name of the shooter.
The stories here continue to build the myth of Jack as a cold-blooded killer, a legendary gangster. Within this chapter, three murders are attributed to Jack, he ruins the life of a young woman, and he is shown to be neck deep in drug dealing. He sleeps with whores and survives drive-by shootings. Sometimes Jack shows reluctance to embrace this exaggerated image of himself. He refuses to indulge the press, claiming that he is just an ordinary citizen and denying all of their embellished stories. At other times, Jack perpetrates his own myth. He tells Marcus about his first murder, although this may be a means of gaining Marcus's trust so that he can use Marcus to smuggle money. Even when he confides in Marcus, Jack does not brag and takes no pleasure in retelling these stories.
Jack's bad guy appeal is reinforced in this chapter when the librarian falls for him so hard that she tries to take her own life when he breaks it off with her. Marcus is attracted to the dangerous side of Jack's character, but he does not want to put himself in too much peril, and refuses to hide Jack's jewels. Marcus wants vicarious thrills from Jack. Marcus is not interested in actually being bad; he prefers seeming bad.
Jack often tries to be a good Catholic. He goes to mass, donates money to the church, and occasionally carries a rosary. But details in this chapter indicate that Jack is not as devout as he likes to seem. Jack's morals are questionable, and he also has a curious fascination with the religious group the Masons. Although he claims to have become a member of the group for business purposes, saying Protestants do not always want to do business with Catholics, the story about how Northrop got him to become a Mason suggests that Jack is genuinely interested in the sect. Moreover, Jack's repeated references to luck implies a belief in elements of the occult.
Jack began to rise through the ranks of the mob by killing a man who gave him four thousand dollars not to kill him. This is the first in a series of personal betrayals that Jack purports or allegedly purports. In addition to his guilt over disrespecting his Irish Catholic heritage, Jack feels guilty about these betrayals.