Archie's cruelty reaches levels that are quite unbelievable. He demonstrates that cruelty without abandon, using it to manipulate anyone who stands in his way, or anyone he simply decides it would be fun to manipulate. He manipulates everyone in The Vigils to supporting his plans, he manipulates every student who gets an assignment, he manipulates Brother Leon and he manipulates the entire student body. Archie's supreme understanding of people comes from an unknown source, but his talent lies in determining what will hurt a person most. Perhaps he assigned Jerry to the chocolates because something told him that this would grow to be bigger than originally planned. Perhaps he envisioned Jerry's strength and ability to resist conformity and knew that he could extend the fight.
The fact that Archie undertakes the sale as a cause and makes someone refuse the chocolates is interesting, as it seems as if he is making it more difficult to fulfill his responsibility. What he is really doing, however, is setting up both Jerry and Brother Leon for a tragic downfall. Knowing their personalities and vulnerabilities, he can alternately plot against both of them by using the sale. Perhaps the single most frustrating element of Archie's approach is he uncanny ability to escape punishment. Everyone knows he is behind the destruction of Room nineteen, Jerry's initial refusal to sell the chocolates and the boxing match. But he does not receive as much as a slap on the wrist for any of these actions. He manipulates Brother Leon into standing up for him—not only because he is helping Brother Leon with the sale, but also because he knows that Brother Leon recognizes the similarities between himself and Archie.