Robby Sassoon: The Hamptons Lawyer's Theatrical Enforcer

Overview

Robby Sassoon is the primary enforcer for crime boss Sonny Blum in James Patterson's The Hamptons Lawyer. He is a meticulously dressed, Broadway-obsessed hitman who takes theatrical pleasure in his work. Unlike the typical thug, Sassoon blends refinement with chilling cruelty—he attends shows, orders fine wine, and tucks his napkin into his collar to avoid staining his shirt with veal sauce or blood. His character serves as the most direct physical threat to protagonist Jane Smith and her partner Jimmy Cunniff throughout the novel.

Plot Role

Sassoon operates as Blum’s instrument of intimidation and murder. He begins by pressuring debtors like Martin Elian and Beth Lassiter, escalates to direct attacks on Jane’s home and dog, and ultimately receives the order to kill Jane and Jimmy. His actions drive the personal stakes of the investigation: he vandalizes Jane’s house, kicks her dog, and shoots up Paul Harrington’s home. He also murders Allen Reese and Jane’s ex-husband Martin. His plot arc ends when Sonny Blum—fearing Sassoon’s ambition—executes him in a surprise betrayal.

Motivations and Traits Shown Through Actions

Sassoon’s primary motivation is professional pride and a desire for order. He calls himself a “practical man” and dresses in “business formal” even during stakeouts. He assesses Bernstien’s cologne correctly—Frédéric Malle, over three hundred a bottle—and takes equal care with his own appearance. The text shows he values aesthetics: he skips dessert because “the aesthetics would be all wrong,” and he sings along to show tunes after a kill. His theatrical flair is evident when he uses Reese’s phone to call police—a “whimsical” touch, as he thinks. He also imagines himself as the rightful successor to Blum, comparing the power structure to King Lear and privately thinking, “For me,” when Bernstein says “It’s going to be good being king.” This ambition reveals a cold, calculating nature beneath the cultured exterior.

His cruelty is methodical. He shoots Beth Lassiter execution-style and stages the scene as a robbery. He crushes Allen Reese’s hand before killing him, displaying sadistic pleasure. He also echoes the same line—“Mr. Reese had an accident”—that he used after a previous murder, showing his ritualized approach. When given the order to kill Jane Smith, he quips, “Why put off until tomorrow when you can kill today?” This line, a play on the proverb, underscores his dark humor and efficiency.

Chronological Arc

1. Early Appearances (Chapters 7, 9): Sassoon first appears as a refined enforcer visiting Café Martin to threaten its owner over gambling debts. He also stalks Jane Smith on the beach, watching Ben Kalinsky propose, but holds back due to a past debt she owes.

2. Escalation (Chapters 26, 28): He vandalizes Jane’s home, kicks her dog out, and later fire a suppressed rifle at Paul Harrington’s house—an intimidation tactic he describes as a “warning shot.” He drives away singing Sweeney Todd.

3. Murders (Chapters 40, 83): Sassoon kills florist Beth Lassiter and real estate tycoon Allen Reese. After each, he enjoys a fine meal and a show tune. He uses Reese’s phone to call police for dramatic effect.

4. Alliance with Bernstein (Chapters 39, 67): He works closely with Jeb Bernstein, discussing Blum’s health and Sassoon’s own ambitions. He pats Bernstein on the head—a gesture others mistake for friendship but which is his calling card.

5. Final Assignment (Chapter 116): Sonny Blum summons Sassoon to his home, praises his work, then shoots him in the head, calling it “poetic justice.” Sassoon dies believing he was about to receive orders to kill Jane and Jimmy.

Relationships

• Sonny Blum: Employer and eventual killer. Sassoon respects Blum but plans to supplant him. Blum, however, sees Sassoon as a loose end.
• Jeb Bernstein: A professional partner and potential rival. They bond over taste and efficiency, but Sassoon inwardly acknowledges he may have to kill Bernstein later.
• Jane Smith: Sassoon considers her a “worthy adversary” after she killed Anthony Licata. He wants her to know it was him who would eventually kill her, but his ambition is cut short.
• Claire Jacobson: Sassoon had an affair with her, taking photos that Blum used to blackmail Rob Jacobson. Claire later shoots Rob Jacobson in the final chapters.

Key Decisions and Consequences

• Deciding to warn rather than kill Jane early (Chapter 9): Sassoon spares Jane’s life when he could have attacked, because Blum had not yet ordered her death. This allows Jane to continue her investigation.
• Killing Allen Reese in a theatrical manner (Chapter 83): He uses Reese’s phone to call police, which delights him but also leaves a clear signature. This act solidifies his reputation but does not protect him from Blum.
• Revealing his ambition to Bernstein (Chapter 67): By hinting at his desire to succeed Blum, Sassoon may have sealed his fate. Blum likely learned of his ambition through Bernstein and decided to preempt betrayal.
• Accepting the assignment to kill Jane and Jimmy (Chapter 116): He arrives at Blum’s home confident he will receive the final order. Instead, Blum kills him. The consequence is his own death, removing the primary physical threat from the story.

Themes and Symbols

• Theatricality and Performance: Sassoon constantly references Broadway—Sweeney Todd, Wicked, Merrily We Roll Along—and treats his murders as performances. This theme of corruption and power is heightened by his view of crime as art.
• Order and Control: His obsession with neatness, fine dining, and exact timings mirrors the need for control in a chaotic life. Even his death is a result of underestimating his own boss’s control.
• Loyalty and Betrayal: Sassoon is loyal to Blum only as long as it benefits him. He plans to betray Bernstein and succeed Blum. This ties to the theme of loyalty and betrayal.
• Mortality: Sassoon’s ambition is driven by his sense that Blum is dying. He sees himself as the natural heir, but his own mortality catches him by surprise. This intersects with the theme of mortality and cancer.

Frequently Asked Questions

• Why does Robby Sassoon kill Allen Reese? Reese failed to pay his gambling debts to Sonny Blum. Sassoon permenently disabled Reese’s hand before shooting him, both as punishment and as a message to other debtors.
• What is Robby Sassoon's ambition? He wants to take over Sonny Blum’s criminal empire when Blum dies. He privately compares the situation to King Lear and thinks “For me” when Bernstein says “It’s going to be good being king.”
• Why does Robby Sassoon spare Jane Smith's dog? He initially kicks the dog out and regrets not shooting it, but he does not have Blum’s authorization to kill Jane or anyone close to her yet. He calls the scene “a Disney movie” but leaves without harming the dog further.
• How does Robby Sassoon die? Sonny Blum shoots him in the head at close range in his Port Washington den, after Sassoon asks for the order to kill Jane and Jimmy. Blum calls it “poetic justice for a hit man.”
• What is Robby Sassoon's calling card? He pats people on the head—a gesture that others mistake for friendship. The text reveals that no one realizes it is his signature until it is too late.

For a full analysis of the novel’s themes, visit the Themes page. To understand the ending and Sassoon’s role in it, see the Ending Explained. If you have more questions about the book, check the Questions and Answers section.