Winter in Paradise

Elin Hilderbrand

47 pages 1-hour read

Elin Hilderbrand

Winter in Paradise

Fiction | Novel | Adult | Published in 2018

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Part 1, Chapter 1-Part 2, Chapter 8Chapter Summaries & Analyses

Content Warning: This section of the guide contains discussion of death.

Part 1: “Stateside” - Part 2: “Little Cinnamon”

Part 1, Chapter 1 Summary: “Irene: Iowa City”

On New Year’s Day, Irene Steele, an editor recently demoted at Heartland Home & Style magazine, is at home in Iowa City. Unable to reach her husband, Russ, by phone, she meets her friend Lydia for dinner. Irene teases Lydia for flirting with a barista, and Lydia notes that Russ is devoted to Irene even after so many years of marriage. Back home, Irene ignores a call from a 305 area code, but when the house phone rings with the same number, she answers. A woman named Marilyn Monroe, secretary for Russ’s boss, informs Irene that Russ has died in a helicopter crash in the US Virgin Islands and reveals that he secretly owned a villa on St. John.

Part 1, Chapter 2 Summary: “Ayers: St. John, USVI”

On New Year’s Eve, Ayers Wilson works a busy shift as a server at a local St. John restaurant. Her ex-boyfriend, Mick, arrives with his new girlfriend, and a coworker takes their table to spare Ayers the interaction. Throughout her shift, Ayers texts with her best friend, Rosie, who is with her mysterious boyfriend, known only as the Invisible Man. After work, Ayers celebrates the new year alone on the beach. The next morning, a distraught Mick comes to Ayers’s door to tell her that Rosie is dead.

Part 1, Chapter 3 Summary: “Cash: Denver”

In Denver on New Year’s Day, Irene and Russ’s youngest son, Cash Steele, learns from his accountant that his two outdoor supply stores have failed. Cash is relieved at the prospect of giving up the business and returning to his former life as a ski instructor. He tries to call his father, but gets his voicemail. Irene calls immediately after to tell him Russ has been killed in a helicopter crash and, surprisingly, owned property in the US Virgin Islands. Stunned, Cash decides to drive to Iowa with his golden retriever, Winnie, and urges Irene to tell no one else until he arrives.

Part 1, Chapter 4 Summary: “Huck: St. John”

On New Year’s Eve, fishing captain Sam “Huck” Powers runs a charter on St. John. His plans change when his granddaughter, Maia, cancels on him, and he ends up spending a quiet evening alone. The next morning, police officers arrive at his home to inform him that his stepdaughter, Rosie, was killed in a helicopter crash. As he processes the news, Huck is grateful that Maia was not home to hear it from the officers.

Part 1, Chapter 5 Summary: “Baker: Houston, Texas”

In Houston on New Year’s Day, Anna, the wife of Irene and Russ’s older son, Baker Steele, writes a list of resolutions, including being more present for her family. Anna, a surgeon, writes the list before leaving for hospital rounds. At the park with their son, Floyd, Baker contemplates divorcing Anna but decides against it. That evening, Anna returns and announces she is leaving Baker for a female colleague named Louisa. Moments later, Irene calls to tell Baker his father is dead.

Part 2, Chapter 6 Summary: “Irene”

Irene speaks with Marilyn Monroe again and learns that a property manager identified Russ’s body, which was cremated without her consent. The next day, Cash arrives and books flights for them to St. Thomas. They agree to delay telling Russ’s elderly mother, Milly, about his death. Irene and Cash fly to Atlanta, where they meet Baker. The three travel to St. Thomas together. During the flight, Irene recalls a difficult family vacation to the Caribbean and dreads the secrets they are likely to uncover on St. John.

Part 2, Chapter 7 Summary: “Ayers”

Ayers finds out the other victims of the crash were the Invisible Man and the pilot. Mick drives Ayers to Huck’s house, where community members have gathered to offer support. Inside, Huck embraces Ayers, confirming the news. He explains that Rosie’s daughter, Maia, is with a friend and does not yet know. Huck asks Ayers to be with him when he tells Maia, and she agrees, resolving to be strong for her best friend’s daughter.

Part 2, Chapter 8 Summary: “Cash”

Cash, Baker, Irene, and Cash’s dog Winnie take a ferry to St. John, where Paulette Vickers, Russ’s property manager, meets them. She drives them to a lavish, secluded villa that she confirms belonged to Russ. While touring the impersonal but elegantly furnished house, Cash finds a framed photograph of Russ with a smiling West Indian woman in a drawer and hides it from his mother. Cash questions Paulette, who reveals she removed all of Russ’s personal belongings on his boss’s orders. She identifies the woman in the photograph as Rosie Small and informs them that a memorial service is being held for her.

Part 1, Chapter 1-Part 2, Chapter 8 Analysis

The novel’s narrative structure establishes the fractured and layered reality that the Steele family will need to confront. Through a multi-perspective, third-person limited point of view, the narrative deliberately compartmentalizes information, granting the reader a more complete, albeit disjointed, picture than any single character possesses. The reader learns of Rosie’s death and her connection to the “Invisible Man” before the Steeles depart for St. John, transforming their journey into a suspenseful collision of two worlds. This structural choice accentuates the isolation of each protagonist within their respective crises—Irene’s work demotion, Cash’s financial ruin, Baker’s abrupt divorce—which are presented in swift succession. These personal cataclysms compound the primary tragedy of Russ’s death, ensuring each character enters the central mystery from a place of profound instability. The shift between the cold, orderly world of Iowa and the tropical community of St. John reinforces the profound schism in Russ’s life before his family uncovers its details.


The juxtaposition of Iowa and St. John mirrors Russ’s divided existence, introducing The Complexities of Living a Double Life. Iowa represents the life of perceived authenticity, Midwestern values, and family history. It is cold, familiar, and predictable, a place where Irene is deeply rooted. As she walks through her hometown, she notes, “She was born and raised right here in eastern Iowa, where the winds come straight down from Manitoba. Russ hates the cold” (7-8). This statement provides an early foreshadowing that Irene and Russ’s life together isn’t a perfect fit. Following the crash, Russ’s identity is immediately bifurcated. In Iowa, he is the doting husband who sends calla lilies and commissions a skywriter to declare his love for his wife. In St. John, Russ is the enigmatic “Invisible Man,” a nickname that underscores his desire for anonymity, spending a week a month with his second family. Irene instinctually rejects the news that Russ owns a villa in St. John in an attempt to protect the established marital narrative that defines her life: “My husband did not own a home in the Virgin Islands. I would obviously know if he owned a home. I’m his wife” (50). The St. John villa symbolizes the scale of this deception, a stark material contrast to the meticulously curated home in Iowa that Irene believes represents their shared life. The impersonal quality of the villa, stripped of all personal effects on Russ’s boss’s orders, emphasizes it as a facade for an alternate life built on dishonesty.


Hilderbrand keeps the details of Russ’s boss, Todd’s identity and the nature of Russ’s work intentionally obscured to build narrative suspense and lay the groundwork for the mystery that drives the next installment of the Paradise series. Although Todd never appears in Winter in Paradise, he’s notable in his absence—a mysterious specter that creates intrigue around the crash that took Russ’s life. Todd is repeatedly mentioned, searched for, and speculated about by Irene and her sons as they attempt to make sense of Russ’s double life. Irene emphasizes that she only met Todd—a college acquaintance of Russ’s—once 13 years prior to the events of the narrative in a chance encounter in a hotel lobby. She notes that the “chance meeting led to a job offer […] Now Todd Croft is just a name” (16). When Irene attempts to call him, she hears a recording that the number is no longer in service. By leaving Todd wholly mysterious and unseen, Hilderbrand provides a subtle throughline to the novel’s cliffhanger ending that reveals the helicopter crash that killed Russ and Rosie involves foul play that has prompted an FBI investigation. Hilderbrand implies that Russ’s work and his mysterious boss are at the center of this foul play.


The introduction of the Steele brothers establishes a fierce sibling rivalry between them that emphasizes the ways they define themselves within their established formative family unit. Positioned as foils, Cash and Baker’s initial reactions to their personal and shared crises reveal different worldviews that will shape their approach to the mystery. Cash, faced with the failure of his business, feels not despair but relief, indicating a rejection of the conventional success his father championed. His role is quickly defined as the nurturer, as he prioritizes his mother’s emotional state, hiding the incriminating photograph of Russ and Rosie to shield her from pain. Conversely, Baker embodies a more traditional alpha-male persona, defining himself as a self-made and self-sufficient man in contrast to his younger brother. His response to Russ’s villa is a “long, low whistle” (67) of astonishment and a focus on the material spectacle and value of the property, while Cash’s immediate concern is for the emotional implications of Russ’s betrayal. This dynamic positions the brothers as representatives of two conflicting legacies of their father: the pragmatic, ambitious man Baker sought to emulate, and a more sensitive, unfulfilled inner self that Cash reflects.


Through the juxtaposition of its primary settings and the initial discontent of its central characters, the narrative interrogates the concept of Paradise as a Façade Versus an Emotional Reality. The novel’s title, Winter in Paradise, is an oxymoron that signals the thematic tension between external beauty and internal turmoil. Iowa is depicted as a landscape of cold, predictable domesticity, a place of “cozy, bread-and-butter values” (5) that Irene has painstakingly shaped into her personal ideal. It represents the knowable, stable world that is about to be irrevocably destroyed. St. John, in contrast, is introduced not as an idyllic escape but as the site of a violent, inexplicable tragedy. The breathtaking vistas and turquoise water are consistently framed by the characters’ shock and grief, creating a profound disconnect between the environment and their emotional reality. The luxurious villa is revealed to be a place of secrets and lies, and its beauty is rendered hollow. By placing a story of profound deception in a setting synonymous with escape and perfection, the narrative suggests that paradise is not a place, but a state of emotional honesty that the characters have unknowingly lacked for years.


Ayers and Huck’s grief over Rosie’s death in the helicopter crash alongside Russ introduces the novel’s thematic engagement with Redefining Family in the Wake of Tragedy. Two distinct grieving units are established in parallel: the nuclear Steele family, shattered and geographically scattered, and the nascent found family of Huck, Ayers, and Maia on St. John. The Steeles’ grief is defined by shock and the weight of uncovering Russ’s many secrets, which complicate their ability to mourn. Her sons, already estranged, are united by the bewildering task of investigating their father’s life and caring for their mother. Conversely, the St. John community’s response to Rosie’s death is immediate and communal, a collective and public processing of grief that contrasts with Irene’s solitary, private experience. The narrative establishes Ayers’s pivotal role in the redefined family structure when Huck asks her to be present when he tells Maia about her mother’s death. This moment evidences the familial bond forged in shared loss, setting a precedent for the kinds of unexpected alliances that will be necessary as the characters navigate the mystery surrounding the crash.

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