Characters With a Vengeance Riley Sager

Anna Matheson Character Analysis

Overview

Anna Matheson is the central figure in Riley Sager's With a Vengeance, a woman whose family was systematically destroyed by a conspiracy of six people. In an elaborate plan, she lures those six conspirators aboard the luxurious Philadelphia Phoenix train, intending to expose their guilt and deliver them to the FBI. Over the course of a single snowbound night, Anna evolves from a grief-stricken schemer into a reluctant avenger, confronting the limits of her own morality and the cost of seeking justice.

Plot Role

Anna initiates and drives the entire narrative. She and her accomplice Seamus orchestrate the boarding of the six invitees – Judd Dodge, Jack Lapsford, Edith Gerhardt, Sally Lawrence, Herb Pulaski, and the absent Kenneth Wentworth (replaced by his son Dante). Her plan is to present irrefutable evidence of their involvement in the troop train explosion that killed her brother Tommy, her father’s frame-up and murder, and her mother’s suicide. Once the train departs, Anna reveals her accusations in the first-class lounge. However, the plan unravels when murders begin – Judd is poisoned and Edith is strangled – turning Anna’s quest for justice into a survival mystery. She must identify the killer while maintaining control of the train and her own sanity. Her role culminates in a face-to-face confrontation with Kenneth Wentworth, the mastermind, and her decision to pull the trigger.

Motivations and Traits

Anna’s primary motivation is justice — not revenge, at least in her own mind. She states she wants the conspirators to face legal consequences for destroying her family. Yet her actions reveal a deep, simmering rage. She carries a knife hidden on her thigh, dresses in blood-red armor, and rehearses a speech she cut off when the train started moving: “I’m here to get justice. Because I have irrefutable proof that the six of you are responsible for destroying my family.”

Traits emerge through her actions:

  • Resilience and composure: Trained by her Aunt Retta, who slapped her randomly to teach her not to flinch, Anna learns to absorb pain, control hatred, and hone emotional stillness. Throughout the night, she remains outwardly calm even when confronted with murders and accusations.
  • Strategic intelligence: She pays off the crew, empties the train of other passengers, and ensures the locomotive will not stop until Chicago. She has backup evidence sent to the FBI.
  • Moral complexity: Despite her rage, Anna is not a natural killer. She hesitates to kill even those she despises. When Seamus reveals he murdered Judd and Edith, she is horrified and says she will never forgive him. Yet at the climax, she shoots Kenneth Wentworth in an act born of exhaustion and rage — a turning point that blurs the line between justice and vengeance.
  • Vulnerability: Anna is haunted by memories of her family. She dreams of her brother Tommy’s mangled corpse. She still harbors fond feelings for Edith and Sal, women she once loved as family, which makes their betrayal cut deeper.

Chronological Arc

Anna’s arc unfolds over the train’s twelve-hour journey. Initially, she is nervous but determined. She waits in her room, checks the manifest, and steels herself for confrontation. When she enters the lounge, she delivers her accusation, naming names and recounting the destruction of her family. The arrival of Dante Wentworth (rather than his father) is an early wrinkle.

After Judd Dodge dies from poison, Anna must pivot from accuser to investigator. She searches the passengers, hypothesizes that the poison was on the glass, and fends off accusations. She confronts Edith, who confesses to hiding files under Kenneth’s blackmail, and later finds Edith strangled. The death of the former nanny, whom Anna once loved, triggers unexpected grief and guilt.

Later, Anna learns that Seamus committed both murders. She confronts him, and he jumps off the train, leaving her alone with the surviving conspirators. She then pursues Reggie, who is revealed as a rogue FBI agent turned hitman, onto the train roof. After a violent struggle, the train stops, and Anna finds Kenneth Wentworth in the cab. In the final chapter, she forces his confession and shoots him. The novel’s brief final chapter, “Arrival,” suggests she reaches Chicago — but the emotional arrival is her acceptance of the violent act she has committed.

Relationships

  • Seamus Callahan: Anna’s accomplice and the “fake conductor.” He is the brother of one of the soldiers killed in the troop train explosion. Their bond is forged in shared grief and a year of planning. Seamus is in love with Anna, but she does not reciprocate. Despite this, she loves him “in her own wounded way.” When she learns he murdered two conspirators without her approval, she feels profound betrayal. His suicide-like jump off the train leaves her alone and armed with his revolver.
  • Dante Wentworth: Son of the mastermind Kenneth Wentworth. Anna and Dante shared a romantic past — they met at a Christmas party, he gave her roses after her performance as Juliet, and they had a brief relationship. On the train, Dante uses the nickname “Annie” to unsettle her. Anna is torn between her lingering feelings and her hatred for his father. Dante is not a target of her rage, but his presence complicates her mission.
  • Edith Gerhardt: The family’s former nanny and housekeeper who called Anna Schatzi (“little treasure”). Edith was blackmailed by Kenneth into hiding files. Anna loved Edith as a child, and both of them struggle with the betrayal. When Anna chokes Edith during the search, it shows her loss of control. Edith’s subsequent murder — and her final confession of regret — leave Anna conflicted.
  • Sal (Sally) Lawrence: Her father’s secretary, whom Anna viewed as a surrogate older sister. Sal confesses to helping Kenneth plant evidence, but claims she didn’t know Tommy would die. Anna is unmoved, but Sal’s words plant doubt about Seamus’s loyalty.
  • Aunt Retta: Anna’s harsh mentor after her family’s deaths. Though cruel — slapping Anna to toughen her — Retta’s lessons in emotional control shape Anna’s ability to face the conspirators without flinching.

Key Decisions and Consequences

  1. Deciding to confront the six on the train rather than let the FBI do the work. This choice places Anna in a volatile situation where she cannot control outcomes. The consequence is two deaths before Chicago, complicating her moral stance.
  2. Not telling Seamus to stop the murders. Though she did not order them, her reluctance to share the full plan leads Seamus to act on his own rage. The consequence is Seamus’s suicide and Anna’s guilt.
  3. Sparing lives during the night. She stops Herb Pulaski from jumping, refuses to kill Lapsford, and does not harm Dante. This maintains her identity as someone seeking justice, not revenge — until the final moment.
  4. Shooting Kenneth Wentworth. She pulls the trigger after he admits destroying her family. This act transforms her from victim to killer. The narrative does not judge her, but the word “Arrival” hints at a new, darker phase of her life.

Theme and Symbol Connections

  • Revenge vs. Justice: The central tension of Anna’s character. She repeatedly insists she wants justice, but her actions — dressing in red, carrying a knife, practicing an accusatory speech — signal a desire for personal vengeance. The murders by Seamus and her own final shot blur this line. The theme is explored at length on our Revenge vs. Justice page.
  • Betrayal and Deception: Anna is betrayed by people she trusted — Edith, Sal, and eventually Seamus. The Betrayal and Deception page delves deeper.
  • Guilt and Redemption: Anna carries guilt over her family’s fate (she once believed she could have saved them) and later over Edith’s death. Her final act may be an attempt to reclaim agency, as discussed in Guilt and Redemption.
  • Family Secrets: The revelation that Kenneth Wentworth is Tommy’s biological father — and that his revenge was personal — ties into the Family Secrets theme.
  • Survival: Anna learned from Aunt Retta to survive through emotional numbness. The Survival page examines how Anna’s learned stoicism both protects and isolates her.

Symbols: The red dress signifies power and passion; the silver locomotive pin represents her father’s legacy; the knife is her potential for violence; the snowstorm mirrors her emotional chaos.

Five Questions and Answers

1. Why does Anna insist she is not a killer, yet she ultimately kills Kenneth?

Anna distinguishes between premeditated murder and a reactive act of justice. She tells Sal, “I’m not a killer.” She restrains herself from attacking Edith and refuses to let Seamus poison Lapsford. But when faced with Kenneth — the man who orchestrated everything and who admits he had Arthur murdered in prison — the built-up rage and exhaustion overcome her resolve. The act is not calculated revenge but a spontaneous, emotional release. The ending explained page discusses this ambiguity.

2. Why does Anna still have fond feelings for Edith and Sal despite their betrayals?

As a child, Anna loved both women as family. Edith was her caretaker; Sal was a surrogate sister. The betrayal is therefore more painful because it comes from trusted figures. Anna’s lingering affection is a sign of her humanity — she cannot simply erase years of care. That emotional residue complicates her quest and makes the confrontations more intimate.

3. How does Aunt Retta’s abuse shape Anna’s persona on the train?

Aunt Retta’s brutal method — slapping Anna until she learned not to flinch — teaches Anna to suppress external reactions. In the lounge, Anna remains composed even as she accuses the conspirators. Retta’s mantra to “absorb your pain, control your hatred, hone your stillness” directly enables Anna to execute her plan. However, it also prevents her from processing grief, which resurface in nightmares and her eventual breakdown.

4. Why does Anna trust Seamus until it is too late?

Anna and Seamus share a singular goal: exposing the conspirators. They met at Aunt Retta’s funeral, where Seamus gave her six boxes of evidence. Over the year of planning, Anna came to rely on him completely. She does not realize that his grief is more vengeful than hers. When Sal suggests Seamus may have killed Judd, Anna initially dismisses it. Her trust is both a strength (she needed an ally) and a fatal blind spot that leads to Seamus becoming a murderer.

5. What is Anna’s internal conflict regarding Dante Wentworth?

Dante represents a past life when Anna was still innocent and capable of love. She uses the sharp nickname “Mr. Wentworth” to keep distance, but she recalls their meetings with both fondness and pain. She knows he is not responsible for his father’s crimes. Dante’s presence forces her to acknowledge that not everyone on the train deserves punishment, complicating her binary view of guilt and innocence.