Though Mamet does not attempt to solicit sympathy for any of his characters, Levene is the closest thing in the play to a tragic figure. From the first moments of the play Levene is a man on the brink of total failure. By trying to elude that failure through any desperate measures he can, he ends up making his troubles all the worse. "Bad luck" is not Levene's only problem. Because he fears failure so deeply, he clings to anything that will make him feel successful. He is often boastful of his past accomplishments with the company, and when he makes a sale to the Nyborgs (which, humiliatingly, turns out to be no good), he instantly starts into regaling the office with his tale of triumph. Moreover, Levene feels that his "success" gives him the upper hand on Williamson, whom he berates whenever he has the opportunity. Of course, we sense that Levene's treatment of Williamson will end up contributing to his own downfall. Levene may very well have been a fine salesman in his youth—though surely not so great as he claims—but now he has grown older and the company no longer has any use for him. Mamet suggests that such a system that teaches people to chase success and detest failure has also trained Levene to self-destruct.
If Levene is the face of failure in the play, then Roma is its best representative of success. His sales techniques are subtle and smart: we can see, in Act One, scene three how he is able to lure Lingk into his sales pitch by using language and discussing issues that are completely counter to traditional sales methods. Rather than overpowering Lingk, Roma is able to put on a show of existential philosophizing that both sets Lingk at ease and draws his interest. As Levene exudes failure, Roma exudes success. But the apparent ease with which Roma conducts his business is deceptive—in fact, he is as tightly wound as any of the other salesmen, and we see at the end that he is planning to exploit Levene in order to advance his success even further. Though Roma has earned a status in the office that should afford him some security in his job, he is every bit as devious as the others. The only difference between Roma's scamming and, for example, Moss's, is that Roma's is smarter, more methodical, and therefore more likely to work.
Williamson, the "company man," is disliked by all of the salesmen because he is indifferent to their concerns. They accuse him of not being a "man" because his job is to implement orders given to him by his superiors. Also, the salesmen resent that Williamson's pay is not based on commission, claiming that he therefore does not know or understand the pressures that the salesmen face. Though Williamson's work as office manager is indeed quite different from sales, what the salesmen fail to recognize is that his motivations are identical to theirs. His job is secure, so it would be foolish of him to risk that by being more of a "man." Nonetheless, when he sees an opportunity to scam—bargaining with Levene to break company policy by selling him two leads for 100 dollars plus 20 percent of Levene's commissions—he is quite willing to put company loyalty aside.
Moss, like Levene, is in his fifties and probably past his prime as a salesman. Moss's response to this possibility of imminent obsolescence, however, is not desperation but anger. Moss understands his business well enough to know that no one is going to help him, and that getting ahead will require him to be proactive and devious. Subtlety, however, is not his strong suit: the verbal trap he sets to try to get Aaronow to commit the office robbery is crude and flawed. Moss picks out Aaronow, and then Levene, to be his partner in crime because he knows that both men are desperate and thus easy targets for him. He fails to consider, however, that their desperation also makes both men unreliable partners in a very delicate scheme. Moss assumes—not inaccurately—that each man is out for himself at all times. He therefore seeks, by whatever means necessary, to exploit others before they exploit him.
Aaronow seems to be faring as poorly as Levene, but his response is one of resigned acceptance rather than desperation. He reveals in conversation with Roma that he is frustrated by his inability to close sales recently, but this frustration is not enough to break him out of his pattern. Aaronow continues to try to sell in exactly the same manner he always has, leading us to presume that his cold streak will continue and will cost him his job. However, he is wise enough to resist Moss's trap, perhaps out of fear or resentment, but likely just as much out of common sense.
Lingk is the one significant character in the play who is not in the real estate business. His weakness makes him a perfect target for Roma. Lingk bends first to Roma's will and then to his wife's will, but at no point does he seem to know what he himself wants or to be capable of making decisions on his own. Lingk's putty-like malleability is the quality all of the salesmen treasure and seek out in others: if a person is willing to give a proverbial inch, then a good salesman can find a way to extract a proverbial mile. Lingk himself seems painfully aware of his own weakness, but, understandably, he is too upset and beleaguered by the bullying and lying that surrounds him to be able to fight against it.