Grace Sampson is a senior middle school English teacher and the head teacher for the eighth grade at the Edward Tilghman Middle School. Sampson is played by Dravon James.
She plays a matriarchal role in the school as many of the students view her as a disciplinary motherly type (all the students act correctly when she approaches them). Grace has a son named Allen, after the boy's father. She had a relationship with Dennis "Cutty" Wise before he was sentenced to a long prison term. When he was released from prison, he tracked Grace down and learned where she was working. She avoids reconnecting with Cutty but offers him help in the form of putting him in touch with her church deacon to help him find work. Cutty visits Grace again when he has established a boxing gym for local kids. She rebuffs his advances again but tells him that she is proud of him. Grace's sister Queenie is a drug addict and is envious of the way her sister has taken control of her life.
Grace is feared and respected by her students who know her as Mrs. Sampson. She is able to subdue a classroom quickly and commands the attention of children easily. As head of the eighth grade she encourages her teachers to use simple, consistent rules in the classroom to make it easy for the students to comply. She is supportive of new teacher Roland Pryzbylewski and helps him with discipline problems in his classes when she can. When a student named Chiquan is attacked by a classmate wielding a box cutter in Pryzbylewski's class, it is Grace who steps in and slaps the violent student to disarm her. She comforts the injured girl and asks a responsible student, Crystal Judkins, to phone for an ambulance.
Grace works with Howard Colvin to establish separate classes for two groups of eighth graders that he terms "corner kids" and "stoop kids." By separating the problem "corner kids" from classes, he hopes that he can address their specific needs and give the other students more time to learn. Grace helps him to identify children who might be considered "corner kids." She suggests Namond Brice. She works alongside Assistant Principal Marcia Donnelly to select another nine students for the class.
Grace sees Cutty once more when he is working as a custodian bringing truanting children into the school. This time both of them are content to leave their relationship in the past.
Actress Dravon James portrays both Grace and her sister Queenie.