The main characters include the two Wes Moores. The author and the other Wes Moore, both African American, were born in Baltimore and raised by single mothers. The author's father (a journalist named William Westley Moore, Jr.) died when the author was young, and the other Wes Moore's father had little to do with him. The author grew up with his half-sister Nikki, who was 7 years older and whose father, Bill, was mostly out of her life. He also has a younger sister Shani, who is very bookish. The author's mother, Joy, was born in Jamaica and grew up in the Bronx before attending American University. After the author's father died, the author lived with his maternal grandparents and mother in the Bronx and attended Riverdale, a private school, where he befriended a boy named Justin, who is also African American.

The other Wes Moore is raised by his older half brother, Tony, who has an intermittent relationship with his father, who lives in a nearby project in Baltimore. The other Wes's mother, Mary, works hard as a secretary and had hoped to attend a four-year college but was disappointed in her hopes. Her mother died when she was young, and she had Tony when she was a teenager.