Shepherdess of the Sphinxes: Symbol Analysis in Killers of a Certain Age

What Is the Shepherdess of the Sphinxes?

The Shepherdess of the Sphinxes is a real surrealist painting by Leonor Fini (1907–1996), housed at the Peggy Guggenheim Collection in Venice. In Deanna Raybourn’s novel Killers of a Certain Age, this artwork becomes a recurring symbol for the four retired assassins—Billie, Helen, Natalie, and Mary Alice—and their late mentor, Constance Halliday. The painting depicts a female figure who gently oversees mythical sphinxes, creatures known for posing riddles and guarding secrets. The women reinterpret this image as a metaphor for their own lives: protectors of dangerous knowledge, guardians of stolen art, and killers who operate in the shadows.

The symbol first appears as a nickname for Constance (Billie calls her “Shepherdess” during a harrowing escape in Chapter 7) and later returns as the centerpiece of the novel’s closing scene in Chapter 32, when the group visits the Peggy Guggenheim Collection in Venice. There, they raise a toast to Constance and to themselves as “necessary monsters,” embracing the painting’s dual message of care and menace.

Where the Symbol Recurs

The symbol recurs only in these two moments, but its resonance echoes throughout the novel. The painting itself is not mentioned during the 1994 Egypt mission (Chapters 22–25) or the 2025 train confrontation, yet the women’s role as shepherdesses of valuable objects—first the Raphael Leda and the Swan, later the entire Nazi-looted hoard—mirrors Fini’s motif.

How Its Meaning Changes

Initially, “Shepherdess” is a private nickname Billie gives Constance when she refuses to abandon her mentor. As Constance suffers a stroke, Billie says, “I know what you’re trying to say. Forget it. I’m not big on rules, remember?” (Chapter 7). Here, the term implies protection of a vulnerable person—a shepherd leading a lost sheep.

By the novel’s end, the meaning expands. The women view the painting together after completing their final mission and securing their retirement. Billie raises a glass and proposes a toast to “the shepherdess of the sphinxes—Constance Halliday—and to the shepherdesses of the sphinxes—ourselves” (Chapter 32). No longer just a reference to one woman, the symbol now encompasses all four. They are no longer merely protectors of art; they are guardians of each other, of the secrets they carry, and of the moral complexity of their violent profession. The sphinxes represent the dangerous knowledge and deadly tasks they have managed throughout their careers. The title “shepherdess” becomes an affirmation of purpose in old age.

Character Connections

• Billie Webster: She first attaches the nickname to Constance, and in the final scene she leads the toast. Billie embodies the symbol’s evolution—from a lone operative to a woman who values her chosen family.
• Constance Halliday: The original “Shepherdess.” Although deceased during the main timeline, her legacy inspires the women. Constance taught them to value the job’s higher purpose: retrieving looted art and eliminating war criminals.
• Helen, Natalie, and Mary Alice: Each accepts the title as part of their group identity. Helen, the sober strategist; Natalie, the eccentric artist; Mary Alice, the pragmatic family woman—together they form a complete version of the shepherdess archetype.

Theme Connections

This symbol weaves together several key themes:

Aging and Competence

The women are called “old” by enemies and by the Museum, yet their final action is to view a painting that celebrates mature female power. Fini’s shepherdess is not a young maiden but a controlled, commanding figure. (See Aging and Competence.)

Loyalty and Chosen Family

Billie’s refusal to leave Constance in Chapter 7 mirrors the group’s later refusal to retire quietly. The toast solidifies their bond as a family of assassins. (See Loyalty and Chosen Family.)

Art and Legacy

The painting Leda and the Swan drives the Egypt plot, but Shepherdess of the Sphinxes becomes the women’s own legacy. Art is not just a commodity they retrieve; it is a mirror for their own existence. (See Art and Legacy.)

Deception and Disguise

As shepherdesses, the women have spent decades hiding in plain sight—as nannies, tourists, bunnies, and wealthy retirees. The painting’s surreal quality (a woman calmly guarding animal hybrids) reflects their own double lives. (See Deception and Disguise.)

Revenge and Justice

The toast occurs after they have eliminated their enemies (Galina, Tamara, Marilyn) and reclaimed the Raphael. Their “necessary monster” label acknowledges that justice sometimes requires monstrous acts. (See Revenge and Justice.)

4 Study Questions with Answers

1. Why does Billie call Constance “Shepherdess” in Chapter 7?
Answer: Billie uses the term as a private code to keep Constance calm after a stroke. It also signals Billie’s defiance of Museum protocol—she will not abandon her mentor, even at risk to her own life.

2. How does the painting Shepherdess of the Sphinxes differ from the painting Leda and the Swan in terms of thematic weight?
Answer: Leda and the Swan is the mission object—a lost Raphael worth millions that the women must retrieve. Shepherdess of the Sphinxes is a personal symbol they choose at the end; it represents their identity rather than a target. The first is stolen art to be returned; the second is found art that returns meaning to them.

3. What does the phrase “necessary monsters” mean in the context of the toast?
Answer: The women acknowledge that their work—killing, deceiving, retrieving stolen objects—is monstrous by ordinary standards. Yet they deem it necessary because they operate in a world where evil (Nazi looters, gangsters, corrupt officials) must be met with force. The phrase reclaims the monster label as a form of agency.

4. In what way does the symbol connect to the novel’s metafictional Author’s Note?
Answer: The Author’s Note opens by claiming that authors are liars and challenges readers to sort fact from fiction. The real painting by Leonor Fini grounds the novel in actual art history, but the women’s interpretation of it is entirely fictional. This mirrors the novel’s game of blending real artifacts with invented stories, making the reader a sphinx who must decode truth.