Bob Sheldon, Cherry Valance's boyfriend and leader of the rival Soc gang, is an all-American teenage boy. He is good-looking, comes from a wealthy family, and enjoys drinking with his friends and picking on Greasers. Bob is condescending and characterizes Greasers as socially inferior "white trash with long hair." His prejudice and self-righteous nature underscore the class warfare between Greasers and Socs.

Bob is also violent and possessive. He grows jealous when he sees Cherry with Ponyboy and Johnny and tracks them down, causing Johnny to stab and kill him. His death symbolizes the endless cycle of violence in Tulsa. Before the story begins, Bob badly beat up Johnny. After Johnny kills Bob, the Greasers and Socs plan a rumble in order to settle the score. Bob's death reflects that cyclical violence is destructive to both sides and the idea that no one ever truly wins. His death is also important because it acts as a catalyst that sets the rest of the story in motion.

Bob reflects the idea that stereotypes cause people to be misunderstood. After his death, the reader learns that there was more to him beneath the surface. Cherry tells Ponyboy that Bob was sweet and kind in private moments. Randy provides insight into Bob's home life and explains that Bob did not have any solid ground to stand on because his parents did not set any rules or limits for him. They let him get away with everything, so he lashed out and acted recklessly in a desperate grasp for parental guidance. In this sense, Bob parallels Johnny. Both boys struggle at home because neither of their parents provide adequate support. Bob is clearly a complicated character, capable of being "hot-tempered" and "cocky" while also being "scared stiff at the same time."

The details that Ponyboy learns about Bob after his death enable Ponyboy to empathize with the Socs. He recognizes that they are also just boys with their own problems and insecurities, which supports Hinton’s notion that stereotypes and caricatures cause harm by oversimplifying a person's character.