When I Was the Greatest

Jason Reynolds

65 pages 2-hour read

Jason Reynolds

When I Was the Greatest

Fiction | Novel | YA | Published in 2014

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Character List

Meet the key characters, with insights into their roles, motivations, and relationships—spoiler-free.

Major Characters

Ali is an almost sixteen-year-old boy living in Bed-Stuy, Brooklyn, with his mother and younger sister. He is focused on his education and staying out of trouble, coping with the anxiety of his personal responsibilities by practicing boxing in the shower. Deeply loyal and highly protective, Ali values his community and shows a level of emotional maturity that sets him apart from peers.

Key Relationships

Best Friend of Noodles James

Friend and Neighbor of Needles James

Older Brother of Jazz Brooks

Boxing Student and Mentee of Malloy

Friend of Tasha

Noodles is Ali’s quick-tempered best friend who lives in the apartment building next door. He has a petty criminal streak and often acts out with loud bravado to mask his deep-seated fears of financial and social embarrassment. Growing up in a bare, neglected home, he struggles with feelings of resentment and anger regarding his older brother's neurological condition.

Key Relationships

Best Friend of Ali Brooks

Younger Brother of Needles James

Romantic Interest of Tasha

Needles is Noodles’s older brother, a nearly seventeen-year-old who has Tourette’s syndrome. He is naturally reserved and often performs small acts of kindness in his neighborhood, contrasting with his loud and uncontrollable physical tics. To help manage his condition, he learns to knit, which gives him a sense of control and calms his physical symptoms.

Key Relationships

Older Brother of Noodles James

Friend and Neighbor of Ali Brooks

Supported by Doris Brooks

Doris is Ali and Jazz’s mother, a social worker who also holds a second job at a department store to support her household. She is a strict but deeply loving disciplinarian who fiercely protects the vulnerable and advocates for those with mental health conditions. Despite her exhausting schedule, she remains a constant, guiding presence in her children's lives.

Key Relationships

Mother of Ali Brooks

Mother of Jazz Brooks

Separated Partner of John Brooks

Advocate and Supporter of Needles James

John is Ali and Jazz’s father, a career thief who was previously imprisoned for armed robbery. Though separated from Doris due to his criminal lifestyle and inability to maintain legitimate employment, he remains an affectionate and communicative figure in his children's lives. He occasionally visits and shares money with Doris, maintaining a strong bond with his family despite secretly living out of his car.

Key Relationships

Father of Ali Brooks

Father of Jazz Brooks

Separated Partner of Doris Brooks

Supporting Characters

Jazz is Ali’s eleven-year-old younger sister, known for her sharp banter and playful sense of humor. She frequently steps into a caretaking role by cooking creative meals like "Spaghetto" for her brother when their mother is working. She uses scrapbooking as a form of escapism, imagining international trips for her family.

Key Relationships

Younger Sister of Ali Brooks

Daughter of Doris Brooks

Daughter of John Brooks

Romantic Crush of Joe

Malloy is a former Vietnam War veteran and double amputee who lives in a brownstone that has been in his family for a century. He serves as a mentor to Ali and other fatherless boys in the neighborhood, using boxing to teach them the value of effort rather than violence. He struggles with alcohol abuse as a coping mechanism for his war trauma.

Key Relationships

Boxing Instructor and Mentor of Ali Brooks

Grandfather of Joe

Black, also known as Kendall, is a neighborhood jack-of-all-trades and entrepreneur. While some dismiss him as a master of none, he is a misunderstood polymath who earns a comfortable living through his various hustles. He forms part of the unseen network of community members looking out for the local youth.

Key Relationships

Romantic Partner of Kim

Community Guardian of Ali Brooks

Informal Barber of Noodles James

Janice is the single mother of Noodles and Needles. She is emotionally and physically absent from her sons' lives, offering them little affection or basic care. She frequently leaves the apartment in inappropriate clothing for mysterious jobs, leaving her children to fend for themselves in a neglected environment.

Key Relationships

Mother of Noodles James

Mother of Needles James

Tasha is a smart, high-achieving teenager who lives in a pristine, gentrified section of the neighborhood with her professional parents. She is a top student whose family owns their brownstone, yet she treats Ali and Noodles with respect and never shames them for their lower-income status.

Key Relationships

Romantic Interest of Noodles James

Younger Sister of MoMo

Friend of Ali Brooks

MoMo is Tasha's older brother and the black sheep of their upper-middle-class family. He is an unemployed high school dropout who is suspected of dealing drugs, though his primary reputation comes from throwing lavish, exclusive parties for the neighborhood.

Key Relationships

Older Brother of Tasha

Candace is an attractive young woman who attends MoMo's exclusive party. She shares an intimate dance and a private moment with Ali, prompting his anxieties about intimacy before their interaction is cut short.

Key Relationships

Romantic Interest of Ali Brooks

Brother runs the local barbershop, which serves as a communal hub and safe haven for the neighborhood. He treats everyone who enters his shop like family and is quick to protect the local youth from unsavory influences.

Key Relationships

Community Protector of Ali Brooks

Kim is Black's girlfriend and is currently in EMT training. She provides medical care for the neighborhood youth when they need it and expects respectful behavior in her home.

Key Relationships

Romantic Partner of Black

Medical Caretaker of Needles James

Ms. Brenda is a reliable neighbor who acts as an extended family member for the Brooks household. She helps Doris by watching the children, participating in the community's collaborative approach to raising its youth.

Key Relationships

Babysitter of Jazz Brooks

Babysitter of Ali Brooks

Neighbor and Helper of Doris Brooks

Joe is Malloy's grandson, described by Ali as a clean-cut, well-mannered teenager. He takes pride in setting a positive example and is highly approved of by Ali.

Key Relationships

Grandson of Malloy

Romantic Crush of Jazz Brooks