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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Character Analysis

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

Irene Steele

As the protagonist of the novel, Irene begins the story as a woman confident in the idyllic life she’s meticulously constructed. An editor for Heartland Home & Style, her identity is deeply intertwined with the restoration of her 1892 Queen Anne home, a six-year renovation project that serves as a tangible representation of her design eye and attention to detail. As the novel opens, her forced “promotion” that she correctly interprets as a demotion, and the loneliness she feels due to her husband Russ’s frequent business trips, signal cracks in the idyllic façade of her life. The news of Russ’s death, the novel’s inciting incident, propels her from a state of comfortable complacency into the role of a determined investigator. Irene is a dynamic and round character whose development is central to the narrative. Her journey from Iowa to St. John allows her to uncover the truth of her marriage and gives her the freedom to decide who she wants to be in the wake of Russ’s death.


Irene’s character is defined by her profound transformation in the face of devastating betrayal. The discovery that Russ not only owned a secret villa but also had a second family dismantles her perception of her 35-year marriage and her own identity as a wife. Her initial reaction is one of disbelief and denial, as when she insists to Russ’s boss’s secretary, “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). This certainty quickly gives way to a methodical search for answers. Her journalistic instincts serve her well as she begins to piece together the puzzle of Russ’s double life. This quest forces her to confront uncomfortable truths, not only about Russ but about her own ignorance. She acknowledges that she preferred the freedom and financial security that came with Russ’s travel-heavy job, rarely questioning the specifics of his work and allowing a comfortable distance to grow between them.


Her evolution is most clearly illustrated through her unlikely alliance with Huck, the stepfather of her husband’s mistress. What begins as a tense, information-seeking encounter develops into a bond forged by shared loss and mutual respect. By the end of the novel, Irene has moved from a state of shock to one of pained acceptance. The discovery that Russ had a daughter, Maia, forces her to expand her conception of family in the most radical way possible. Her journey represents a fundamental re-creation of self, as she navigates a world where the foundations of her life have irrevocably shifted.

Russ Steele

Russ Steele serves as the novel’s central catalyst, a character whose actions, revealed posthumously, drive the plot. Though he is dead before the story begins, his presence looms large, and his character is constructed through the memories of his family and the shocking evidence of his secret life. To his Iowa family, he is a doting, if often absent, husband and father, known for grand romantic gestures and a seemingly transparent, earnest personality. This image is contradicted by the discovery of his second life on St. John, where he is known as the “Invisible Man,” a wealthy, reclusive figure with a villa, a mistress, a secret daughter, and a mysterious business. This duality renders Russ as a flawed figure, epitomizing the novel’s thematic exploration of The Complexities of Living a Double Life.


Russ’s characterization is built on the stark contrast between his two worlds, a juxtaposition symbolized by the stark differences between the novel’s two settings, Iowa and St. John. In Iowa, he is a middle-class businessman whose success affords his family a comfortable, respectable lifestyle. In St. John, he is the owner of a multi-million-dollar villa, living a life of luxury and secrecy. The people on the island know him as a private person who “liked to keep a low profile” (63), a description that stands in sharp opposition to the man who hired a barnstormer plane to declare his love for his wife in the skies over Iowa City. His motivations are left ambiguous, forcing the characters to question whether his actions stemmed from a place of genuine love for two separate families, a sociopathic need for control and secrecy, or involvement in illicit activities that required such a fractured existence.


Ultimately, Russ’s character functions as a mystery to be solved. The helicopter crash that kills him provides the novel’s inciting incident and a symbol of the violent destruction of the illusions upon which his family’s lives were built. His two lives, once carefully separated, collide in the wake of his death, forcing his two families to confront the wreckage of his deceit. He is a static character, as his identity is fixed by his death, but the perception of him is highly dynamic, shifting dramatically as each new secret is unearthed. His legacy is not one of love or success, but of the profound and painful questions he leaves behind for those who thought they knew him.

Baker Steele

Baker Steele, Irene and Russ’s eldest son, is a deuteragonist whose personal crisis mirrors the novel’s central themes of betrayal and deception. Initially, he presents as the more stable and conventional of the two brothers. He is a stay-at-home father and day-trader, living in the shadow of his high-achieving cardiothoracic surgeon wife. On the surface, his life appears settled, but just before learning of his father’s death, Baker discovers that Anna is leaving him for a female colleague, a revelation that shatters his own domestic “paradise” and complicates his ability to judge his father’s transgressions. Baker is a round, dynamic character who is forced to re-evaluate his identity as a husband, father, and son.


Baker’s primary internal conflict stems from his rigid worldview being dismantled. He is initially judgmental of his brother Cash’s freewheeling lifestyle and business failures, indulging in a sense of superiority as the more responsible son. However, the discovery of Russ’s immense, secret life, coupled with his own marital collapse, forces him into a state of moral confusion. In St. John, he’s confronted with a reality far outside his comfortable Houston existence. His journey is marked by a struggle to process two simultaneous betrayals: his wife’s and his father’s. His immediate and intense infatuation with Ayers represents a desire for a fresh start, an escape from the lies that have defined both his marriage and his family history. This attraction, however, places him in direct competition with Cash, exposing the long-simmering tensions between the brothers.


His role in the story is to explore the ripple effects of the central deception. While Irene seeks the truth and Cash provides emotional support, Baker is often caught in a state of reactive disbelief, his pragmatism clashing with the unbelievable circumstances. He is more reluctant than Cash to dig into the past, stating, “What is it going to benefit you or me to know the answers? She was a woman Dad was screwing down here. How will it help to know any more?” (85). This resistance highlights his desire to avoid further pain and complications. However, his feelings for Ayers draw him deeper into the St. John community and, by extension, into the heart of his father’s secret world, forcing him to confront the very truths he wishes to avoid.

Cash Steele

As the younger Steele son, Cash Steele is initially portrayed as a carefree “ski bum,” a foil to his seemingly more grounded and responsible older brother. The novel opens with Cash facing a significant failure: the collapse of his two outdoor supply stores, a venture financed entirely by his father. His first reaction to the news of Russ’s death is a guilty wave of relief that “I don’t have to tell him about the stores” (25), a moment that reveals his fear of paternal disappointment. This initial immaturity, however, quickly gives way to a deeper sense of duty. Cash is a dynamic character whose journey is marked by a rapid maturation as he steps into the role of his mother’s primary emotional support.


Cash’s defining trait is his sensitivity, which allows him to connect with his mother, Irene, on a level that Baker cannot. Irene is the parent with whom he shares a closer bond, and he’s the first person she calls after learning of Russ’s death. Without hesitation, he packs up his life in Denver to drive to Iowa and accompany her to St. John, immediately taking charge of the practical and emotional logistics. While Baker is often paralyzed by shock or distracted by his own marital problems, Cash adopts a more investigative and protective role. He is the one who questions Paulette about the details of Russ’s life on the island and the first to discover the photograph of Russ with Rosie, a secret he attempts to shield from his mother.


Throughout the novel, Cash grapples with his identity and his place within the family. His father’s constant encouragement to build an “infrastructure” was a source of pressure, and the failed business represents his inability to live up to Russ’s and Baker’s more conventional standards of success. The revelations about his father’s secret life, however, reframe this dynamic. He sees that his father’s own “infrastructure was built of lies” (69), which, while devastating, also frees him from the burden of his own perceived failures. His emerging sense of self is further complicated by his attraction to Ayers, which creates a romantic rivalry with Baker and forces him to confront his lifelong feelings of being second-best. His journey is one of stepping out from his father’s and brother’s shadows to become a person on whom his mother can rely.

Ayers Wilson

Ayers Wilson serves as the narrative bridge between the Steele family’s world of idyllic ignorance and the hidden reality of Russ’s life on St. John. A hardworking and independent woman, Ayers juggles two jobs as a waitress at the island’s best restaurant, La Tapa, and a crew member on a charter boat. Her story runs parallel to Irene’s, as she is grappling with her own recent betrayal. At the start of the novel, she is nursing a broken heart after discovering her long-term boyfriend, Mick, cheating on her. This personal experience of infidelity provides a counterpoint to the grand-scale deception the Steeles uncover, grounding the novel’s thematic interest in Paradise as a Facade Versus an Emotional Reality in the everyday lives of the island’s residents.


Ayers’s most significant role in the narrative is as the keeper of Rosie Small’s memory. As Rosie’s best friend, she provides an intimate perspective on the woman who was Russ’s mistress. Her fierce loyalty and profound grief offer a humanizing portrait of Rosie, preventing her from being reduced to a one-dimensional “other woman.” Ayers’s relationship with Rosie was one of deep, sisterly love, and her devastation at the loss is palpable. Following Rosie’s death, Ayers immediately steps into a protective, maternal role for Rosie’s 12-year-old daughter, Maia Small, promising the grieving girl, “You’re always going to have me” (79). This commitment demonstrates her immense capacity for love and loyalty, qualities that draw the Steele brothers to her.


Ayers is a dynamic character who finds her own life becoming deeply entangled with the Steele family’s tragedy. Her steadfast rule against dating tourists is challenged by her simultaneous attraction to both Baker and Cash, the sons of the very man whose secret life indirectly led to her best friend’s death. This complicated romantic triangle forces her to navigate her grief while also contending with a new and confusing emotional landscape. Ayers embodies the resilience of the St. John community, representing a life lived with integrity and authenticity in a place where others come to hide their secrets.

Huck Powers

Huck Powers, the stepfather of Rosie Small, acts as a moral anchor in the story and a guardian figure for his granddaughter, Maia. A seasoned fishing captain known to everyone on St. John as “Huck,” he is a pragmatic and respected member of the island community. Though initially presented as a gruff, solitary man who is grieving the loss of the young woman he raised as his own, he quickly reveals a deep well of kindness and wisdom. His world, already upended by Rosie’s death, is further complicated by the arrival of the Steele family, forcing him to confront the full scope of the secret life Rosie led with the “Invisible Man.” Huck is a round, dynamic character whose fierce protectiveness of his family is ultimately matched by his capacity for empathy.


Huck’s primary motivation is his unwavering love for Maia. He is her “Unconditional,” her “No Matter What” (79), and every decision he makes is filtered through the lens of her well-being. This devotion informs his initial wariness of Irene. As the wife of the man he holds responsible for Rosie’s secret life and, ultimately, her death, Irene represents a threat to the stable world he is trying to maintain for Maia. However, their first meeting evolves into an unexpected alliance. During a day spent fishing, they discover they are not adversaries but “casualties of the same sordid circumstances” (169), two people connected by a shared, complex grief. This bond is central to the novel’s exploration of Redefining Family in the Wake of Tragedy.


Huck serves as a critical bridge between the insular world of St. John and the outsiders from Iowa. He provides Irene with crucial context about Rosie’s life and the community’s perspective, while also acting as a gatekeeper of information to protect Maia. His relationship with Irene develops from one of mutual suspicion to one of genuine friendship and unspoken attraction, suggesting the possibility of healing and new beginnings. He embodies a quiet, sturdy integrity that contrasts sharply with Russ Steele’s duplicity, representing a form of maturity grounded in loyalty and responsibility rather than secrecy and control.

Rosie Small

Though she is deceased before the novel begins, Rosie Small is a pivotal character whose memory and choices are central to the plot. She is primarily characterized through the loving recollections of her best friend, Ayers, and her stepfather, Huck. To them, she was a vibrant, beautiful, and fiercely loyal woman who was deeply rooted in her St. John community. As a single mother, she was devoted to her daughter, Maia. However, her defining characteristic in the context of the story is her intense privacy regarding her long-term relationship with Russ, the man known on the island only as the “Invisible Man.”


Rosie’s acceptance of this secret relationship makes her a complex and somewhat tragic figure. For years, she lived a bifurcated life, maintaining her public identity as a local waitress and mother while privately sharing a luxurious villa with a wealthy man whose full story she kept hidden even from her closest confidantes. This secrecy suggests a deep-seated conflict within her. While she seemed content, her desire for an engagement ring indicates a longing for a public acknowledgement of their relationship that Russ could never offer her. Her insistence on privacy was, as Huck suspects, a condition set by Russ, but it also served to protect herself and Maia from the judgment of the close-knit island community. The photograph of her and Russ in the hammock, discovered by Cash, serves as the first tangible proof of their intimate, established relationship, transforming Russ’s betrayal from an abstraction into a reality with a human face. Her story illustrates the compromises one makes for love, and the devastating consequences of a life built around a secret.

Maia Small

As the 12-year-old daughter of Rosie and Russ, Maia is the most tangible and innocent consequence of Russ’s double life. She is a bright, resilient, and emotionally perceptive girl who is forced to navigate an unimaginable tragedy—the sudden loss of her mother. Initially, her existence is a shocking revelation to the Steele family, representing the ultimate secret her father kept. However, Maia is not merely a symbol of Russ’s betrayal; she is a fully realized character grappling with her own complex reality. She is a budding entrepreneur, starting a bath bomb business with her friend, and her decision to return to school shortly after her mother’s death demonstrates a maturity beyond her years.


Maia is the biological link between the two families Russ created, and the characters’ reactions to her reveal their capacity for forgiveness and love. Huck’s devotion to her is absolute; he is her primary guardian and protector. Ayers, as Rosie’s best friend, immediately steps into a supportive, surrogate mother role. The greatest test, however, lies in her meeting with Irene, Baker, and Cash. This encounter forces the Steeles to confront the living, breathing result of their patriarch’s deception. The revelation that Russ is, in fact, her biological father—a truth Rosie and Russ had only recently shared with her—fundamentally alters the family dynamic and solidifies Maia’s place as Baker and Cash’s half-sister.

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