Who does Squeaky race against in "Raymond's Run"?

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Squeaky races against Gretchen in the May Day race.

Gretchen is the new girl.  Squeaky doesn’t like her because her former friend Mary Louise has gone over to her, and she talks about Squeaky “like a dog.”  The two of them are part of a contingent of only six girls running the May Day race, which Squeaky values highly.  She says she wins every year.

One of the reasons Squeaky does not like Gretchen is because she thinks she makes fun of her older brother Raymond.  Raymond is Squeaky’s older brother, but he acts younger, and Squeaky is very protective of him.  When she sees Gretchen and her friends coming down the street, she considers ducking into a candy store.  She decides this is cowardly, and faces Gretchen, telling her she will win because she always does.  Squeaky feels threatened because Gretchen is new.

Squeaky is distracted the day of the race, looking for Gretchen.  She gets offended when an adult, Mr. Pearson, asks her to let someone else win for a chance.  Yet she keeps looking for Gretchen.  When Gretchen comes in second place, Squeaky has a new respect for her.

And I lean down to catch my breath and here comes Gretchen walking back, for she’s overshot the finish line too, huffing and puffing with her hands on her hips taking it slow, breathing in steady time like a real pro and I sort of like her a little for the first time.

After the race, Squeaky feels a new appreciation for Gretchen.  The girls actually smile at each other, a real genuine smile.  Squeaky realizes that she and Gretchen have a lot in common, actually, and are better as friends than as enemies.  

We stand there with this big smile of respect between us. It’s about as real a smile as girls can do for each other, considering we don’t practice real smiling every day, you know...

Squeaky has not just learned to respect Gretchen.  She has also learned to respect herself.  Taking care of Raymond, and standing up for him against all of the abuse others dish out, is hard.  With this race, she realizes that Raymond is a person too (she finds out he is a good runner), and she finds a way to make friends.  It no longer has to be Squeaky against the world. 

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