Mile High (Windy City, #1)

Stevie Shay is the novel’s other protagonist and first-person narrator. In the narrative present, Stevie is 26 years old and lives in Chicago with her twin brother, Ryan Shay. She and Ryan grew up with their parents in Nashville, Tennessee. Since her childhood, Stevie has had a fraught relationship with her mom, which has influenced how she sees herself as an adult. Her mom is white and “a traditional Southern belle” (183) who expected Stevie to follow in her footsteps and participate in the superficial social events that she cared about in her own youth. Stevie has always had a closer relationship with her dad, who is Black, because he accepts her for who she is. By contrast, her mom ridicules and criticizes Stevie for her curvy figure, her thrift store clothing, and her volunteer work at the dog shelter. Stevie’s mother also criticizes her daughter’s lack of interest in resuming a relationship with her emotionally abusive college ex-boyfriend, Brett. These maternal difficulties make Stevie feel insecure, and her past relationship with Brett has also compromised her ability to value and love herself.

Stevie works as a flight attendant on the Raptors’ private plane. She likes the job because of its flexible schedule and because she enjoys travel. The job also introduces her to infamous hockey bad-boy Evan Zanders, with whom she eventually falls in love. At first, Stevie tries to ignore her attraction to Zanders because her disastrous relationship with Brett has compelled her to avoid getting involved with selfish athletes again. Over time, however, Stevie starts to see the real Zanders and discovers that he and she have more in common than she thought. She and Zanders are both interested in charity work and value their relationships with their loved ones. They are also working through their past trauma and are eager to find someone who will love and accept them for who they are.

Stevie’s relationship with Zanders helps her to embrace her true self and to reclaim her voice. With Zanders, Stevie doesn’t feel insecure or unworthy, as Zanders values Stevie for her gentle heart and her fierce spirit. His belief in her and his investment in her life help her to believe in herself again. Stevie also proves herself to be capable of change even when Zanders isn’t around. After their breakup, she takes steps to stand up for herself, use her voice, and pursue her dreams of her own volition. She wants to grow and discovers that she can do so with or without Zanders. Therefore, when she and Zanders get back together, Stevie has become a more confident and balanced person who is better able to love and support Zanders, even as she follows her own dreams.

Eli Maddison is a secondary character. He is Zanders’s best friend, Logan Maddison’s husband, and Ella and MJ Maddison’s father. While Zanders is publicly known for his temper and promiscuity, Maddison is known as “hockey’s golden boy” (6). In reality, however, Maddison and Zanders are more similar than most people understand. Years before the primary events of the novel, Maddison and Zanders grew up in Indiana together and were rivals, but during their college years, they connected over their parallel mental health challenges. They encouraged one another to get help for their respective needs and helped one another grow and change. Not long after they began playing for the Raptors, they co-founded Active Minds of Chicago, a charity through which they support young children with similar mental health challenges.

In the narrative present, Maddison is an integral part of Zanders’s life. The friends play on the same professional team and live across the street from one another. They spend much of their spare time together, and Maddison and his wife have invited Zanders into their family. Maddison sees Zanders as an uncle to his children and supports him as if he is his brother. Maddison therefore acts as a guide to Zanders, listening to his troubles, offering him advice, and encouraging him to be his truest self. Maddison’s role in the novel is to inspire many of Zanders’s steps toward positive change.

Logan Maddison is a minor character. She is Eli Maddison’s wife, Zanders’s close friend, and Ella and MJ Maddison’s mother. Like her husband, Logan plays a supportive role in Zanders’s life. She listens to him, gives him advice, and encourages him when he is feeling discouraged. She also becomes Stevie’s friend and welcomes her into her family. Like Maddison, Logan is honest, accepting, and loving, and she contributes to Zanders and Stevie’s personal growth journeys.

Ryan Shay is Stevie’s twin brother. When Stevie gets her job with the Raptors, Ryan invites Stevie to live with him in his Chicago penthouse. Ryan is a professional basketball player and is often on the road for work. When he’s home, he and Stevie spend time together and talk openly. Ryan proves himself particularly supportive of Stevie after she reveals the truth about her fraught relationships with his friend Brett and their mother. Instead of minimizing Stevie’s trauma, Ryan promises to create boundaries in his own relationships with Brett and their mom as a show of solidarity. Ryan is protective and loving and does everything in his power to support Stevie and guard her safety.

Indy Ivers is Stevie’s supportive friend and coworker. They meet when Stevie starts working for the Raptors. Stevie immediately feels drawn to Indy and is comfortable in her presence. Indy is “tall and slender, her skin sporting a natural sun-kissed glow, with blonde hair running smoothly down her back” (10). She looks very different from Stevie, but she never makes Stevie feel insecure about her appearance. Indy is accepting of Stevie throughout the novel and offers her a closer friendship than she has ever had with other women in the past.