Dean Cartwright in Play Along: Character Analysis

Overview

Dean Cartwright is a secondary but pivotal character in Liz Tomforde's Play Along, the fourth book in the Windy City series. He is Kennedy Kay's stepbrother, a second baseman for the Atlanta team, and Isaiah Rhodes's longtime rival. Though he initially appears as an antagonist—opposing Kennedy's marriage to Isaiah and clashing with him on the field—Dean's arc culminates in a sincere apology and a revelation that reshapes Isaiah's understanding of Kennedy's choices. The text presents Dean as a product of a dysfunctional family, whose anger and resentment toward Isaiah stem from his own insecurities and absent father. By the end, he demonstrates growth, vulnerability, and a protective love for Kennedy, making him more than a simple foil.

Plot Role

Dean functions as both an obstacle and a catalyst in the narrative. Early in the story, he pressures Kennedy to attend a family dinner and reveal her marriage to deflect their parents' attention from his baseball career (Chapter 10). During a game in Atlanta, he confronts Isaiah at second base, accusing him of marrying Kennedy to spite him or for her money (Chapter 11). This confrontation highlights the existing rivalry and adds tension to the fake-marriage arrangement. Later, in Chapter 33, Dean seeks out Isaiah in the training room to apologize for their childhood rivalry. In doing so, he reveals that Kennedy turned down a job offer in San Francisco to stay with Isaiah—a secret that Isaiah had not known. This revelation is a turning point, forcing Isaiah to confront the depth of Kennedy's feelings and his own guilt about her sacrifice. Dean thus moves from being a source of conflict to a source of crucial information that deepens the central romance.

Motivations and Traits Shown Through Actions

Dean's motivations are rooted in his family history and his relationship with Kennedy. The text shows that he was "angry as a kid" and took it out on Isaiah because his own life felt miserable (Chapter 33). He explains that his father was absent, throwing money at him rather than showing up, and that the one game his father attended, he praised Isaiah instead of Dean. This resentment drove Dean to bully Isaiah, steal his girlfriends, and flaunt his wealth. His actions are driven by envy and a need to feel powerful when he felt powerless.

Dean's protective nature toward Kennedy is also evident. He reveals that he watched her cry herself to sleep during her arranged engagement to Connor, and that he felt guilty because she was forced into that situation partly because he refused to take over the family business (Chapter 33). His initial fury at her marriage to Isaiah stems from his fear that she was again trapped in an unwanted relationship. However, his willingness to apologize—prompted by Kennedy's threat to cut him off—shows that he values his relationship with her more than his pride. He admits, "I'm not that guy anymore," indicating a capacity for self-reflection and change.

Chronological Arc

Dean's arc spans from childhood rivalry to adult reconciliation. The backstory, revealed through Kai in Chapter 22 and Dean himself in Chapter 33, establishes that Dean and Isaiah grew up in the same town and competed in baseball. Dean's resentment festered through high school and into their professional careers. In the present timeline, Dean first appears as a demanding stepbrother who insists Kennedy attend a family dinner (Chapter 10). He then confronts Isaiah on the field (Chapter 11), showing his continued hostility. The turning point comes in Chapter 33, when Dean seeks out Isaiah to apologize. He explains his childhood anger, his father's neglect, and his guilt over Kennedy's past. He also reveals Kennedy's sacrifice, which Isaiah had not known. This moment transforms Dean from an antagonist into a figure of empathy and honesty. By the end, he has shaken Isaiah's hand and expressed genuine remorse, indicating a resolution of their long-standing feud.

Relationships

With Kennedy

Dean and Kennedy share a close, sibling-like bond, despite being step-siblings. Kennedy describes him as "one of my closest friends" (Chapter 2). Dean is protective of her, having witnessed her unhappiness during her arranged engagement. He is also the one who pressures her to reveal her marriage to their parents, showing that he sees her as a tool to deflect attention from his own career—a selfish act that also reflects his desire to keep family peace. His apology to Isaiah is motivated by Kennedy's ultimatum, demonstrating that he fears losing her more than he values his pride. He reveals her secret to Isaiah because he believes Isaiah should know the truth, even though it complicates things.

With Isaiah

The rivalry between Dean and Isaiah is central to Dean's character. It began in childhood, with Dean resenting Isaiah's perceived advantages—a caring brother, natural likability, and a stable family. Dean's actions—stealing Isaiah's girlfriends, flaunting wealth—were attempts to diminish Isaiah. The rivalry persists into adulthood, as seen in the on-field confrontation. However, Dean's apology marks a shift. He acknowledges that he was "a little shit" and that he took his anger out on Isaiah. Isaiah, for his part, initially dismisses the apology but eventually accepts it, noting that he no longer cares because he has "everything I've ever wanted." The reconciliation is mutual, and Dean's revelation about Kennedy's sacrifice deepens Isaiah's understanding of both Dean and Kennedy.

With His Father

Dean's relationship with his father is a source of deep pain. His father was absent, using money as a substitute for presence. The one game his father attended, he praised Isaiah instead of Dean, fueling Dean's resentment. Dean admits that his father "tends to bring out the worst in me," indicating that his father's presence still triggers his worst behavior. This relationship explains much of Dean's anger and his need to prove himself.

Key Decisions and Consequences

Dean's most significant decision is to apologize to Isaiah. This act, prompted by Kennedy's threat to cut him off, has several consequences. It allows Isaiah to let go of his own resentment, and it leads to the revelation of Kennedy's sacrifice. Dean's decision to reveal that Kennedy turned down the San Francisco job is a turning point for Isaiah, who had been planning to encourage her to take the job. This revelation forces Isaiah to reconsider his own actions and his guilt. Dean's apology also strengthens his relationship with Kennedy, as he proves he is willing to change for her sake.

Another key decision is his initial insistence that Kennedy attend the family dinner and reveal her marriage. This decision creates tension and forces Kennedy to navigate her family's expectations, but it also leads to a moment where Isaiah defends her and they grow closer. Dean's actions, while sometimes selfish, ultimately contribute to the central couple's development.

Theme Connections

Dean's character connects to several themes in the novel. Performance vs. Authenticity is evident in Dean's public persona as a successful athlete who hides his private pain. He presents a confident, wealthy exterior while struggling with feelings of inadequacy and resentment. His apology is a moment of authenticity, where he drops the facade and admits his faults. Family Expectations vs. Personal Autonomy is central to Dean's backstory: he refused to take over the family business, which indirectly led to Kennedy's arranged marriage. His guilt over this drives his protective behavior. Learning Intimacy and Vulnerability is shown through Dean's willingness to apologize and reveal his emotions, a departure from his usual defensive stance. His vulnerability allows for reconciliation and deeper understanding. While Dean is not directly tied to the themes of grief or gender discrimination, his presence highlights the impact of family dynamics on individual choices.

Questions and Answers

1. Why did Dean initially oppose Kennedy's marriage to Isaiah?

Dean opposed the marriage because he feared Kennedy was trapped in another unwanted relationship, given her history with an arranged engagement. He was also furious that she married his longtime rival, Isaiah, which felt like a personal betrayal. His anger was rooted in his protective love for Kennedy and his unresolved rivalry with Isaiah.

2. What did Dean reveal about Kennedy's sacrifice?

Dean revealed that Kennedy had turned down a job offer as the lead doctor in San Francisco to stay with Isaiah. He told Isaiah that she received the offer on a Tuesday while she was in the training room with him, and that she chose to remain in Chicago for him and for herself.

3. How does Dean's relationship with his father affect his behavior?

Dean's father was absent and used money to compensate, which left Dean feeling neglected and resentful. When his father praised Isaiah at a game, Dean's jealousy intensified. This relationship explains his anger and his tendency to lash out at others, as he took out his frustrations on Isaiah during their childhood.

4. What role did Dean play in Kennedy's past arranged marriage?

Dean was indirectly responsible for Kennedy's arranged engagement to Connor. Because he refused to take over the family business, Kennedy was forced to marry someone who would. Dean witnessed her unhappiness and felt guilty, which is why he is so protective of her later in life.

5. How does Dean change over the course of the novel?

Dean evolves from a bitter rival to a remorseful and honest figure. He apologizes to Isaiah for his childhood behavior, acknowledges his faults, and reveals a painful truth about Kennedy's sacrifice. His willingness to be vulnerable and to change for Kennedy's sake demonstrates significant personal growth.

For a deeper exploration of the novel's themes, see the themes overview and the ending explained. You can also revisit the main book page or browse common questions.