In chapter twenty-one, four new characters are introduced. First, best friends Kevin Chartier and Danny Arcangelo discuss their mutual distaste for the chocolate sale over the telephone. They agree the Jerry has the right idea in refusing the chocolate sale, and wish that they could do the same. Kevin is an inside member of The Vigils, and is careful when discussing the topic with Danny, for fear Danny will let something secret slip. Next, Howie Anderson and Richy Rondell stand outside, lasciviously watching a girl read from a rack of newspapers outside a shop. They discuss Jerry's refusal to sell, and conclude that in this era of "do your own thing" Jerry is completely within his rights to refuse the chocolates.
Obie has left a note for Archie to meet him at the gym. Archie is disgusted by the smell of the gym, and knows that Obie has purposely chosen this venue to annoy him. While he waits for Obie, he reflects that he has no time to enjoy his life anymore - he is always worrying about his bad grades or Vigils assignments. Obie reports to Archie that Jerry has continued his refusal to sell. He explains to Archie that this is a Vigils problem because Jerry is now not just defying the school, but the Vigils, as well. As always, Archie pretends not to care. Obie taunts Archie, asking him if he promised Brother Leon support for the chocolate sale.
In chapter twenty-two, Brian Cochran must report to Brother Leon that the number of boxes sold is falling below last year's levels. Cochran reads off the name of each boy who has sold chocolates, and the number of boxes he has sold, while Brother Leon listens, nodding ominously. When Jerry Renault is reached, his total "zero", Brother Leon says that Renault has infected the school with a sense of apathy. Cochran is left with the feeling that Brother Leon is plotting some kind of revenge on Jerry.
Later, Jerry and Goober are running to the bus stop. Jerry has a seen a girl he likes at this bus stop before, and ascertained her name - Ellen Barrett - by looking at the notebook she was carrying. He hopes to speak to her, or to call her and ask her out on a date. As they run, Goober tells Jerry that he is going to quit the football team. He is disgusted by the state of things at Trinity, and is particularly upset that the unscrewing furniture prank that he was assigned caused Brother Eugene to have a nervous breakdown. Jerry tries to persuade Goober to keep playing football, but Goober refuses, saying that there is something rotten in the school. As Jerry continues to try to persuade him, Goober counters by saying "Sell the chocolates, Jerry." Jerry realizes that Goober's reasons for quitting football are not dissimilar from his own reasons for refusing to sell the chocolates. When they reach the bus stop, Ellen is not there.
In chapter twenty-four, Brother Leon calls Archie on the telephone, beginning the conversation with, "You're in trouble, Archie." The Acting Headmaster tries to bully Archie into pushing the chocolate sale, and is at turns threatening and wheedling. Archie knows from a discussion with Cochran that Brother Leon has overextended the school's finances for the chocolate sale, and that its failure would be disastrous for him. Brother Leon blames Jerry - and, by extension, The Vigils who had originally assigned him to refuse the chocolates - for the failure of the sale. Archie says that it is just that the students are tired of selling, and this year's quotas are too high. Brother Leon ends the telephone call with a threat. He says that if the chocolate sale is not a success, he will dismantle The Vigils.
A Vigils meeting is called in chapter twenty-five. Archie interrogates Renault in front of the whole group, taunting and humiliating him. The boys participate, claiming to have sold more chocolates than they actually have. Jerry stands his ground, though he is frightened, and continues to refuse to sell them. Archie gives another assignment, saying that Jerry must now accept the chocolates. He threatens him with a punishment - probably physical - if he doesn't obey, but when the meeting ends, Archie knows that Jerry will not comply.
The addition of two more vignettes of minor characters speaks to the general change of morale in the student body. Very few of the boys relish the sale, but the pressure to conform and avoid confrontation leads them to go along with both The Vigils and Trinity's administration. Now, however, we see the burgeoning seeds of dissent: they boys are still unwilling to follow Jerry's example, but they voice their admiration for his bravery.
Obie's hatred for Archie is matched only by his fear of him. Frequently throughout the novel, Obie's internal dialogue reveals his desire to seek revenge on Archie or to otherwise orchestrate his downfall, but he is ultimately paralyzed in his efforts to disobey his "leader." Archie seems to actively cultivate that hatred, perhaps instinctually understanding the Machiavellian principle that it is better for a leader to be feared than loved.
Finally, the full extent of Brother Leon's malfeasance is becoming clear. Not only has he overstepped his authority by using money he should not have for the chocolate sale, but he is not above spreading propaganda about the sale to the student body to drum up support. Leon is a character of almost pure ambition and self-interest; he gives little thought to the effects of his power-hungry actions on the young men with whom he has been entrusted. The fact that Archie, Cochran, Caroni and the others are hardly blind to Leon's lack of integrity is perhaps the most damaging aspect of his character. An authority figure, and one of a religious order, who stoops to lying, blackmail, threats, theft, and propaganda - in addition to making deals with an underground student hazing organization - is not the kind of teacher who can inspire faith and a love of learning in adolescent boys. While Archie may be the most active agent of cruelty in this book, with Emile the most visibly sadistic, Brother Leon is without a doubt the most villainous. His lack of care for his students and his total focus on the gratification of his own ambitions infect Trinity with the "evil" Goober detects. The irony is that it is not Jerry's refusal to participate in the sale that is filling the school with apathy, but rather Brother Leon's ambitions and moral turpitude.
While Jerry is the main victim of the novel, Goober is a secondary casualty. His collapse after his assignment and his realization that Leon is evil eventually lead him to abandon everything that he formerly cared about, including his friend, Jerry. His collapse is of a less spectacular nature than Jerry's - he is less heroic, and far more fallible - but it no less than the destruction of a personality. Goober's suffering, and especially his pain over being the cause of Brother Eugene's collapse, breaks him. While this kind of suffering makes Jerry more recalcitrant and defiant, Goober's suffering renders him cowed and defeated. The portrayal of the human effect of tyranny and cruelty on ordinary, unheroic individuals like Goober is perhaps the most important and poignant lesson in the novel.
A clear foreshadowing of the violence that will soon be directed at Jerry occurs in chapter twenty-five. Archie dislikes violence (or so he says), but he threatens Jerry with physical punishment nevertheless. Carter, the president of The Vigils, thinks that Jerry would be more easily convinced by blows than by vague and subtle threats. Since Jerry is determined to stand his ground, his physical safety is almost certainly threatened.