Gregory Bailey is really smart; he gets all A's from what we can gather. Of course, grades aren't always a measure of intelligence, but you have to be bright to get grades like these. Or, you have to be cheating, which everybody knows Bailey is not.
In fact, this is what makes the sick game Brother Leon plays with Bailey so effective. In Chapter 6 (the only chapter in which Bailey makes an appearance), Brother Leon accuses him publically of cheating. To rub in the seriousness of the accusation, Leon hits Bailey on the check with his pointer.
Then Leon proceeds to interrogate and mess with Bailey's head for the rest of the class period. Specifically, Brother Leon tries to make Bailey admit he's been cheating, because nobody but God could get perfect grades. Near the end of the class period, an anonymous class member calls out for Brother Leon to "let the kid alone" (6.50). This is just what Leon's been waiting for.
Leon does a quick turnaround, pretending that his purpose in torturing Bailey, who he knows doesn't cheat, was to show Bailey that his classmates are too spineless to defend him. He turns to the other students and says, "You turned this class into Nazi Germany for a few moments" (6.55).
This is one of the freakier moments in the book. In fact, what Leon does in the classroom with Bailey is very similar to the techniques used by the Nazis during the Holocaust. The Nazi Party was a recognized political party, and the people of Germany voted this party into power. But, even those who didn't approve of Hitler and didn't have any hard feelings toward Jewish people were implicated. The Nazis used physical and emotional violence to force even the unwilling into service, and to turn a blind eye to the mass murder of the Jewish people. (We highly recommend Markus Zusak's novel The Book Thief, which shows how this was done. Essentially, Brother Leon is using Nazi-like techniques to dominate his students. It works, although they know full well that Leon is bogus.
Although Gregory Bailey's character isn't developed until the sequel, Beyond the Chocolate War, the scene in which he stars is important to understanding The Chocolate War. Through this scene, author Robert Cormier is arguing that school situations like the one we see at Trinity could be educating students in using Nazi techniques, which is the last thing any of us wants.