Act Two, which is not divided into scenes, takes place in the office where the salesmen work. It is the day after Act One, and someone has committed the robbery that Moss had been planning. A police detective, Baylen, is on the scene, conducting interviews in Williamson's office offstage. Aaronow and Williamson are onstage at the opening of the scene. Roma comes in from the streets. He is furious; he just heard about the robbery and demands to know if the thieves stole the contracts. Having closed the Lingk sale the previous night, Roma should be over the dollar amount he needs to sell in order to win the Cadillac in the company sales contest. If something has happened to the contract, however, he will not get his prize. Roma, of course, is completely unwilling to accept this possibility. After some yelling from Roma, Williamson assures him that he has nothing to worry about. The thieves did not get the Lingk contract, as it was filed downtown last night.
Williamson goes into his office, offstage, with Baylen. Roma and Aaronow remain onstage. Aaronow makes some meek and nervous comments about how everything should be fine as long as the office is insured. Roma tries to strike up conversation with Aaronow, and Aaronow complains about how poorly he is doing on the board. Roma reassures him, telling him that he has been given terrible leads and has had bad luck, and that his poor performance is not his fault.
Roma starts to head out to the Chinese restaurant. Williamson comes out of the office and asks him where he is going, and why he is not going out on sits. Roma asks how he can go out on sits if the Glengarry leads have been stolen. Williamson offers a lead from last year's file, which Roma derisively refers to as the "nostalgia" file. Having no other options, however, Roma angrily accepts. Williamson goes into the office to get leads for Roma.
Roma and Aaronow have another moment together. Roma suggests that talking to the detective is a waste of time, because he thinks the cops are too stupid to find the robber. Not really meaning it, Roma asks Aaronow if he was the thief. Aaronow says no, but that he gets nervous talking to the police nonetheless.
Williamson comes out with the leads for Roma. The first lead is a man named Ravidam Patel. Just as Moss railed against deadbeats named Patel in Act One, Roma launches into a furious tirade about how impossible it is to close a sale to a Patel.
Levene enters the office, oblivious to the disarray and signs of a break-in, bursting with excitement because he closed a sale to a couple, Bruce and Harriett Nyborg, that morning. He demands to be put on the contest board. After a moment of bragging, he notices that things are amiss, and the others inform him of the break-in.
Whereas Act One serves as a three-part prelude that introduces us to the characters and their motives, Act Two brings all of the characters together—along with a seventh, Baylen, though his presence is merely functionary—to interact in a more complex scenario. The structure of Act Two is much more conventionally "dramatic" than that of Act One: Mamet generates great suspense by concealing the identity of the thief and letting the audience wonder whether or not the thief will be caught. Whereas Act One holds our attention by drawing us into the world of the characters, Act Two uses the information we have from the Act One as a springboard to a more dynamic mode of storytelling.
The scene begins with tension. We know that a robbery has occurred and we know from Act One, scene two, that Aaronow is the most likely suspect. Mamet thus makes a kind of joke by opening the scene with Aaronow speaking an innocuous, nonsensical comment about mathematics. For the first time in the play, Mamet has us in suspense—we wonder if Aaronow has committed the crime, if he has been caught already, if he will be caught—but the characters' conversation is the height of banality. In doing so, Mamet reminds us that all of the drama, or lack thereof, is in the talking.
When Roma enters the scene, his hysterics stand in stark contrast to his smooth talking in the last scene. Roma is a breathtakingly good salesman, but when his guard is down and he is not trying to sell something, his simple greed and anger are animalistic. Seeing his outburst, we can appreciate even more what a fine performer he is. When he wants to, Roma can completely mask his natural anger, concealing it under the face and voice of a master salesman.
Aaronow mumbles about insurance, as if to pray that everything can be restored to normalcy. He is clearly nervous, but we cannot tell at this point whether this is because he committed the theft or just because he had foreknowledge of the robbery. We know that Aaronow has not turned in Moss yet, and that he is therefore hiding something even if he did not commit the crime himself.
Guilty or not, Aaronow finds himself in a double bind. When Roma tells Aaronow to just tell the truth because "It's the easiest thing to remember," we sympathize with Aaronow: he cannot tell the truth, and while perhaps Roma could get away with "selling" a lie to the police, we know that Aaronow is not nearly as good a salesman as Roma is.
When Levene tells the other salesmen about his triumphant sale to the Nyborgs, for the first time we hear Levene referred to by his nickname: "The Machine." Thus far in the play, Levene has been a failure, an embarrassment, but now that he seems to have found some success, he is "The Machine" again—a nickname that we surmise was given to him long ago, when he was still "hot." However, it is possible that someone gave the nickname to Levene sarcastically. Indeed, one of Levene's great weaknesses is a tendency to believe what he wants to believe: as we see later in the scene, he deludes himself to believe that the Nyborg sale will stick, and also succumbs easily to Roma's flattery routine. Whoever first called Levene "The Machine" may very well have been making fun of him, but Levene, in his desperation to feel successful, would not have noticed. Note that Roma, a far greater salesman than Levene ever was, does not have or need a nickname.
Though the notes say that "Early in this scene, Roma tells Baylen that he had heard about the robbery from Moss, and Baylen wondered how Moss knew.", when Baylen asks, Roma cites the board on the window and never mentions Moss.
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