does it have to do with the fact that he chooses the path to the prison?
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Daru lets the prisoner choose to go to prison or freedom. The prisoner chooses prison. This is ironic since prisoners usually prefer to be free. Also when Daru returns to school, he sees the chalk scrawled on the board, "you have betrayed our brother. Now you will pay for this." Daru in fact had let the prisoner free to choose where he wanted to go.