Character Analysis
Simon is Augie's older brother and a regular presence in the novel. Although raised in much the same environment as Augie, he has a different personality, value system, and course of life than his younger brother.
For a little while Simon, like Augie, dips his hand into a variety of ventures—some fruitful and some foolish. Unlike his brother, he's not a romantic idealist, picturing some vague far off future. He sets his sights on an obtainable objective and shoots after it.
First a Lover then a Fighter
Early on in his adult life, Simon sets his sights on marriage. He gets engaged to Cissy Flexner, a girl from their neighborhood. He doesn't have the dough to pay for all the expenses, and he makes some foolish decisions, like getting beat up after losing a bet on a White Sox game. Come on Simon, who bets on the White Sox? That's just asking for trouble. Then Simon becomes enraged when Cissy calls off the engagement. He goes to her house, breaks chairs, and has the police called on him. He spends the night in prison. Cissy definitely made the right decision to dump his angry butt.
Switched Priorities
Eventually Simon's focus pays off for him. Now willing to sacrifice love for money, Simon courts a wealthy young heiress named Charlotte Magnus. He convinces her—and her family—that he'll use the money he gets to build more wealth. He's not interested in living comfortably, but in working hard throughout his life. He convinces the Magnuses, who take a liking to him, and he marries Charlotte.
True to his word, Simon becomes a successful businessman. Unfortunately, he also becomes a ruthless one. He uses his contacts with the police to intimidate troublesome customers. He demands special treatment for his mother in the retirement home. He's also cruel to Charlotte, joking with her that "Nobody's ever been laid better at any price" (11.53). Yuck.
A Family Man—Sort of
When Simon introduces Augie to the Magnuses, he puts on a show, telling Augie in their presence how much better the Magnus family is than their own: "you can see how unlucky we were not to have this kind of close and loyal family. There isn't anything these people won't do for one another" (11.57).
For all his talk of family loyalty, Simon can be hard on his own. When he begins an adulterous affair, his attitude is that Charlotte can just do the same, and "that's her problem if she can't" (22.99). However, he does love his mother and his brothers. He even tries to bring Augie into a similar arrangement with Lucy Magnus, but matchmaking isn't his forte.
Something of a Snob
Wealth makes Simon desire only the best for him and his own. When Augie goes to a county hospital to have an operation so he can enlist and go to war, Simon visits him, but Augie also tells us this:
Simon came to see me and threw a bag of oranges on the bed. He bawled me out that I hadn't gone to a private hospital. His temper was bad and nothing and nobody was spared in his glare. (22.71)
To Augie, the outcome of Simon's decision to become one of the Magnuses—in effect doing what Augie refused to do with the Renlings—confirms that he, Augie, made the right decision. Simon gains wealth and a wife, but he's also always angry at something and generally unpleasant to be around. Augie's like, kthxbai.
Simon's Timeline