In the introduction, Moore (the author) explains that the book tells the story of himself and another man named Wes Moore, both of whom were born in Baltimore in somewhat similar circumstances. However, where Moore himself grew up to achieve great things, “the other” Wes will spend every day of the rest of his life in prison for his part in the murder of Sergeant Bruce Prothero. After learning about Wes, Moore begins a correspondence with him that eventually turns into in-person visits in prison. The two men agree to work collaboratively in order to produce a book about their lives that will hopefully give an insight into the nature of destiny and inspire young people to make positive choices.
In the first interlude, Moore and Wes discuss the impact that their father’s absences had on their lives. While Moore is deeply emotional just thinking about his father, who passed away when he was young, Wes is bitter about his own father’s (chosen) absence from his life.
Chapter One begins when Wes is three years old and playfully punches his older sister, Nikki. His mother, Joy, is furious. Moore explains that Joy immigrated to the United States from Jamaica when she was young. As an undergraduate at American University, Joy met an attractive man named Bill who later became her husband and father to Nikki. However, it soon became clear that Bill had a drug abuse problem; he was also violently abusive to Joy. Ultimately, Joy chose to leave Bill, and not long after met Moore’s father, Westley. Westley was a radio journalist who had graduated from Bard College and hosted his own public affairs program. One day after work, Westley feels ill and goes to the hospital. The doctors send him home with an anesthetic, but the next day Westley collapses and dies of acute epiglottis, a virus that causes suffocation. Although Wes and his younger sister Shani are too young to properly understand what has happened, Nikki is devastated by her stepfather’s death.
The narrative switches to Wes’s family. Wes’s mother, Mary, is an undergraduate student at Johns Hopkins before federal cuts mean that her Pell grant is terminated, and she is forced to drop out. Wes’s older half-brother, Tony, lives with his father and grandparents in the notorious Murphy Homes Projects. Wes feels protective of his mother, as his father, Bernard, is not present in his life. Mary’s mother, Alma, died of a failed kidney transplant when Tony is a baby, and her father, Kenneth, is an alcoholic. When Wes is eight years old, he meets his father for the first time, as he is sitting on Wes’s grandmother Mamie’s couch in an alcoholic stupor.
Two years later, Mary and Wes have moved to Northwood, a safer neighborhood in the Northeast Baltimore. Wes plays football for the Norwood Rams, one of the best rec football teams in the country; yet despite being naturally intelligent, his academic grades are poor. One day, Wes is playing football with some kids from his neighborhood and gets into a scuffle with one of them. As the conflict escalates, Wes’s friend Woody urges him to stay calm, but Wes runs into his house and grabs a knife. The police are called and both Wes and Woody are put in handcuffs.
Meanwhile, Joy and the kids have moved in with Joy’s parents, James and Winell. The Bronx neighborhood in which Moore’s grandparents live has been badly impacted by the crack epidemic and increasing levels of gang violence. James and Winell met as teenagers in Jamaica before immigrating to the United States. James is a minister, and both play an important role in the local community. They establish strict rules for Moore and the other children, but they are also loving and supportive.
Nervous about the prospect of sending Moore to public school in the Bronx, Joy opts to send him to Riverdale, a prestigious private school that was attended by John F. Kennedy. Moore is one of the only black kids in school, along with Justin, a friend who is also from the Bronx. The two boys are teased about attending a “white school,” and Moore begins to feel increasingly conflicted and alienated both in his neighborhood and at Riverdale. As a result, his grades slip; a concerned Joy threatens to send him to military school, but Moore does not take this seriously.
Back in Baltimore, Tony has recently been shot during a botched drug deal. As he recovers in hospital, Wes begins to envy his older brother’s expensive wardrobe. Wes sees a group of kids wearing headsets without realizing that they are working as lookouts in the drug trade, and asks where he can get one; the kids explain that that they are paid to wear them. Skipping school one day, Wes discovers Mary’s weed stash and gets high for the first time. That night, he decides to join the drug game.
In the second interlude, Moore and Wes discuss maturity. Moore states that he believes he became a man when he first became responsible for others; Wes notes that providing for others can be difficult. Wes argues that both he and Moore received “second chances” when they were young, but that a second chance is only meaningful if it involves a change of circumstances.
Chapter Four begins when Wes is fifteen and has been working in the drug game for three years. Tony has noticed that his little brother has a large collection of brand-new sneakers and angrily interrogates Wes about where he is getting the money from. Wes insists that it is from DJing—the same lie he has been telling Mary—but Tony doesn’t believe him. Later, Mary discovers a stash of Wes’s drugs and flushes them down the toilet. Wes, panicked and furious, yells that at Mary that she has thrown away $4,000.
In the Bronx, Moore continues to perform badly in school. One day he and his friend Shea are spray-painting their “tags” on a wall when they are stopped and handcuffed by the police. While Shea shrugs off the incident and behaves rudely to the police officers, Moore is tearful. However, the next week he is back on the streets spraying graffiti again.
The narrative jumps forward in time; Joy has made good on her threats and Moore is now in military school. The final straw came when Moore was playfully hitting Shani and accidentally split her lip. In Moore’s first few days at Valley Forge Military Academy, he is rude to his superiors and attempts to run away four times. During the final time, he is caught and brought to the office of Colonel Battagliogli, who allows Moore to speak on the phone for five minutes. Moore begs to come home, but Joy insists that he must stay. After the call, Moore is assigned to be mentored by Captain Ty Hill, a 19-year-old African-American man who is a distinguished cadet.
Wes is popular with women and has “a dozen girlfriends,” including Alicia, who becomes pregnant only two months after meeting Wes. This news is revealed to Wes’s family during Mary’s baby’s first birthday party; Tony is also about to become a father himself. Despite Alicia’s pregnancy, Wes fails to stop seeing other girls, and one day gets into a fight with one of these girls’ boyfriends, Ray. The fight quickly escalates into a shootout, with Wes and his boys chasing Ray down the street. Ray is shot in the shoulder and Wes is arrested.
Wes’s friend Woody makes it to graduation, but most of their other friends do not. Wes was lucky to be sentenced in a juvenile court for the attempted murder of Ray, and serves only six months in a juvenile detention facility. After getting out, Wes lives with his Aunt Nicey and begins dealing drugs again. At peak efficiency, Wes’s crew brings in $4,000 a day. One day, Wes accidentally sells drugs to an undercover cop and finds himself arrested again.
Military school has had a transformative impact on Moore. He is now disciplined, polite, and hard-working. A star basketball player, he is sent recruitment letters from a large number of colleges, though Moore’s Uncle Howard reminds him to have a backup plan as, despite his talent, he is statistically unlikely to make it to the NBA. Meanwhile, Justin writes with news that Shea has been arrested for possession with intent to distribute. One evening, Moore and another cadet, Dalio, walk to the pizza place in a local town when they are harassed by a group of drunk teenagers, one of whom claims to be Colonel Bose’s son. The teenagers shout racist abuse and throw a heavy object at Moore’s face, but he chooses not to retaliate, instead ensuring that both he and Dalio get home safely.
In the final interlude, Moore asks Wes if he thinks that people are products of their environments. Wes admits that he does, and that he believes that people’s fates are determined by other people’s expectations; if they are expected to succeed, they will succeed, and if they are expected to fail, they’ll fail.
Moore is now training as a paratrooper. He has discovered a love of reading and has been particularly inspired by Colin Powell’s autobiography. He has decided to stay at Valley Forge’s junior college to earn his associate’s degree and is one of the youngest officers in the entire American military.
Wes now has two children with Alicia and two with Cheryl, a 23-year-old woman struggling with an addiction to heroin. Wes has grown sick of the drug game and wishes to get out. He asks his friend Levy for advice, and the two of them enroll in the Jobs Corps program. Wes adores the Jobs Corps campus, earns his GED in record time, and thrives in his vocational training as a carpenter, even building a house for his daughter. However, things become more difficult back in the outside world; Wes earns minimum wage working temporary, menial jobs and has no time to spend with his family. Eventually, he starts dealing drugs again.
The narrative jumps forward in time again. Mary has just learned that Tony and Wes are wanted for the murder of an off-duty cop, Sergeant Bruce Prothero, during a jewelry store robbery. She is aggressively searched and interrogated by the police, who even interrupt Aunt Nicey’s daughter’s wedding to question the guests about Wes and Tony’s whereabouts. In reality, Wes and Tony are hiding out at their uncle’s house in North Philadelphia. After 12 days, the men are found and arrested. While Tony accepts a plea deal to avoid the death penalty, Wes maintains his innocence and his case goes to trial. He is found guilty and sentenced to life in prison.
Moore, meanwhile, is in his senior year at Johns Hopkins University and completing his second internship with Mayor Kurt Schmoke. Schmoke advises Moore to pursue the prestigious Rhodes Scholarship, which Moore is awarded. The next semester, Moore travels to South Africa for a study abroad program. There, he meets Mama and Zinzi, who teach him about the legacy of apartheid and the maturation rituals of the Xhosa tribe. It is while Moore is in South Africa that he first learns about Wes.
In the epilogue, Moore provides an update on each of the major characters in the book. Wes is a grandfather at 33 and is serving the tenth year of his prison sentence. Most of Moore’s family members have found success and happiness, whereas most of Wes’s continue to struggle, and both Tony and Cheryl are dead. Moore himself has led an extraordinary career. After graduating from Oxford with a master’s degree in international relations, he works at the White House and on Wall Street, serves in Afghanistan, and marries his “best friend,” Dawn. Moore reiterates that it is difficult to identify any single factor that caused the differentiation between his and Wes’s destinies, but that the support of Moore’s family and community had an enormously positive impact.
In the afterword, Moore notes that some readers were disappointed by his lack of conclusive statement on what made the difference between his and Wes’s fate. He adds that each reader tends to come up with their own answer, which is the way it should be. Moore is moved that so many people enjoy the book, and admits that he was particularly heartened to hear from a 15-year-old in juvenile detention who told him that the book inspired him to make positive changes in his life.
In the “call to action,” Tavis Smiley argues that the book helps to show how people’s destinies are shaped, and that it encourages the reader to realize their own power. He advises the reader to try their hardest and let God “take care of the rest.”