The conflict of "Raymond's Run" is about how Squeaky is going to prove herself, both as a runner and as a protective sister to Raymond. One quote related to this conflict is "But now, if anybody has anything to say to Raymond, anything to say about his big head, they have to come by me." Squeaky is very protective of Raymond, albeit in the way a sister would typically defend a small younger sibling. In actuality, Raymond is older than Squeaky is. Later, she figures out a way to protect Raymond and champion him without treating him like a small child. When she is running in the May Day races, she thinks, "it occurred to me that Raymond would make a very fine runner. Doesn’t he always keep up with me on my trots?" She decides at the end of the story to prove herself and help Raymond at the same time by coaching him as a runner.
In the meantime, while Squeaky is trying to figure out how to protect Raymond, she attempts to prove herself as a runner. She says, "Now some people like to act like things come easy to them, won’t let on that they practice. Not me. I’ll high-prance down 34th Street like a rodeo pony to keep my knees strong." Squeaky is determined to win races to prove her mettle, and she'll work hard to do so.
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