The Chocolate War

Why does Brother Leon single out gregory bailey to pick on ?

Because he was quiet

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Baily is made an example of for no reason other than to humiliate him and validate Brother Leon's power. Chapter six's scene of mock repression (which results in actual pain and fear - another example of Brother Leon's depravity) has a profound effect on Jerry. He is the mute witness to the completely unwarranted public humiliation of Bailey,