This story is about a protagonist nicknamed Squeaky and follows her preparation to win the upcoming May Day races. Yet the story is titled "Raymond's Run," which includes the name of her older and intellectually challenged brother. This reflects the importance of the story's ending, when Squeaky recognizes her capacity to help her brother achieve his own success.

When she is lining up for the race, Squeaky realizes that her brother Raymond is lining up to run outside the fence that divides the participants from the spectators. As she races, she notices that Raymond races along with the participants, and the sight of him "on his first run" is so powerful that Squeaky nearly stops racing herself to watch him.

After the race, Raymond is overjoyed and climbs the fence to join his sister, who has won. Watching his dexterity as he scrambles over the fence, Squeaky realizes that "Raymond would make a very fine runner." She considers all the ways that she might find success in the years ahead and realizes that Raymond will not have as many opportunities. With Raymond's race in mind, Squeaky begins to imagine leaving her own racing success behind so that she can coach Raymond and give him a greater opportunity to become a victor. Watching Raymond's run is the catalyst for Squeaky's shift in perspective, and this character development is significant to the story.