Chapter summaries The Hamptons Lawyer James Patterson & Mike Lupica

Chapter Thirty-Nine Summary: Robby Sassoon and Jeb Bernstein's Walk

⚠️ Spoiler Warning: This guide contains detailed spoilers for the entire novel. Proceed only if you've finished reading or are comfortable knowing the plot.

Summary

Robby Sassoon and Jeb Bernstein walk north along the East River Greenway. The chapter reveals that Robby was the one who blew up Bobby Salvatore’s boat, and that he spared Anthony Licata that day by telling him to get off the boat. Robby later learned it was Jane Smith who killed Licata in Montauk, making him respect her as an adversary. Now he wants her to know he is the one handling her—unless her cancer becomes more aggressive first. The two men discuss Martin Elian, whom Robby recently intimidated into paying on schedule. Bernstein explains why people still use his illicit bookmaking service rather than legal online options: weekly settlements, less government tax, and the ability to float debt. He notes that even cops and judges now place bets with him. Finally, Bernstein relays a request from Mr. Blum: Robby is to “take care of this matter with her.” Robby agrees to do it today, then pats Bernstein on the head—a signature gesture that Bernstein mistakes for friendship but that Robby knows is a calling card.

Key Events

  • Robby and Bernstein walk and talk about their enemies, including Cunniff and Jane Smith.
  • Robby recalls destroying Salvatore’s boat and sparing Licata; he now respects Jane Smith.
  • Robby describes his meeting with Martin Elian, whom he terrified into compliance.
  • Bernstein explains the advantages of his traditional bookmaking operation over legal online gambling.
  • Bernstein gives Robby a new assignment from Mr. Blum, ordering him to kill “her” (Jane Smith).
  • Robby accepts the job without hesitation, promising to do it today.
  • Robby pats Bernstein on the head, a gesture that will later signal danger.

Character Development

  • Robby Sassoon: His calculated, orderly nature is on display—he dresses formally even for a walk, avoids city traffic, and thinks in terms of practical solutions. His respect for Jane Smith shows that he admires competence in an adversary, though he intends to kill her himself.
  • Jeb Bernstein: He is presented as a natural in the underworld: well-dressed, articulate, and as ruthless as Salvatore. His background working for the NFL underscores his comfort with bending rules. He is loyal to Mr. Blum and unaware of the true meaning of Robby’s head pat.
  • Martin Elian (mentioned): Offstage, his terror at Robby’s visit reinforces Robby’s reputation as an enforcer.

Themes, Symbols, or Motifs

  • Order vs. Chaos: Robby’s obsession with order—his suits, his route, his calling card—contrasts with the messiness of the criminal world. He imposes order through violence.
  • Loyalty and Betrayal: Bernstein and Robby act as a team, but Robby’s private thoughts reveal a transactional relationship. The head pat symbolizes the hidden threat beneath apparent cooperation.
  • Old vs. New: Bernstein’s bookmaking thrives against legal online betting because it offers simpler, less-taxed service. The chapter contrasts old criminal methods with modern regulation.
  • The Inevitability of Death: Robby’s line “Why put off until tomorrow what you can kill today?” treats murder as a routine task, highlighting the fatalistic tone of the novel.

Why This Chapter Matters

This chapter is a turning point. It confirms that Robby Sassoon is the assassin targeting Jane Smith and establishes the timeline for a direct confrontation. It deepens the world of organized crime in the novel, showing how bookmaking has evolved but still relies on enforcers like Robby. The dialogue between Robby and Bernstein reveals the power structure under Sonny Blum and sets up the central conflict: Jane Smith vs. Robby Sassoon. The head-pat motif also adds a layer of ominous foreshadowing for Bernstein’s fate.

Study Questions and Answers

  1. Why does Robby Sassoon respect Jane Smith even though he plans to kill her?
    He respects her because she was the one who killed Anthony Licata in Montauk, showing that she is a capable and worthy adversary. He wants her to know that he is the one handling her death, making it a personal contest rather than a random hit.

  2. What advantages does Jeb Bernstein claim his bookmaking operation has over legal online gambling?
    Bernstein says his service offers weekly or monthly settlement, avoids the complex TV-advertised systems, provides a less-taxed product, and allows customers to float debt—until they abuse the privilege.

  3. What is the significance of Robby patting Bernstein on the head at the end of the chapter?
    The gesture is Robby’s calling card, though no one realizes it until it is too late. Bernstein interprets it as camaraderie, but for Robby it is a silent warning or a mark of doom, foreshadowing that Bernstein may not survive his association with Robby.

Navigation

Previous Chapter: Thirty-Eight | Next Chapter: Forty | Back to Book Hub