Augie makes his way back to Chicago with a detour to see his brother George who despite his mental handicap is "a man of fine appearance, as he had been a beautiful child." He is being trained as a shoemaker. After he leaves, he wishes he could find a way other than institutionalization for his brother: "I thought how quick we were to latch onto the excuse to deal practically with any element, like jailbirds, orphans, cripples, the weak-brained or the old." So he goes from the one institution to the other, the one where his mother lives. Simon has kept their mother supplied with everything that his money can buy, though his occasional visits are mainly to check to see if the money is being well-spent. "I knew how Simon could be when he was doing something for your good and welfare; he could make things hot."
Augie's mother frets about how thin he is, and urges him to see his brother, so Augie complies. Simon turns out to be eager to see him, and Augie "found out that I couldn't be critical of Simon when I saw him after a long interval. No matter what he had done or what he was up to now, the instant I saw him I loved him again." But he has no intention of telling him the full story of what had happened in Mexico. "I didn't say anything about the bird or my failures and lessons. Maybe I should have. He criticized me anyway in his mind for my randomness and sentiment."
But Simon really wants to talk about himself anyway, about how successful he has been and how much money he has made, buying and selling businesses. "Since he didn't want to have to do with the Magnuses he had gone into other kinds of business and he was very lucky." He tells Augie, "If I'm not a millionaire soon there's a hitch in my arithmetic." But of course now he wants to take Augie on as a project. They go to Simon's opulent apartment where Augie is forced to get rid of his old clothes and Simon dresses him in new and expensive ones. He has the old clothes thrown down the incinerator. They go to his office where Simon wheels and deals on an international scale: "He was in on a deal to buy some macaroni in Brazil and sell it in Helsinki. Then he was interested in some mining machinery from Sudbury, Ontario, that was wanted by an Indo-Chinese company." They go to Simon's club where "he forced his way into a poker game. I could tell he was hated, but no one could stand up to him" as he slanders the other players.
Augie asks why he wants to make them hate him, and Simon replies, "Because I hate them. I want them to know it." So why does he belong to a club with people he hates? "Why not? I enjoy being a member of a club." (Which is the flip side of Groucho Marx's line about not wanting to be a member of any club that would let him in.)
On the way home they pick up Charlotte, "grimly handsome and immense." Then Mrs. Magnus arrives, and Augie witnesses the bizarre relationship of Simon and his mother-in-law. He nags her about her cheap clothes, and when she comes to the table he sits there reading the paper and ignoring her.
But suddenly Simon threw himself across the table, spilling the cherries and overturning coffee cups. He grabbed his mother-in-law's dress at the collar, thrust in his hand, and tore the cloth down to the waist. She screamed. There were her giant soft breasts wrapped in the pink band. What a great astonishment it was to see them! She panted and covered the top nudity with her hands and turned away. However, her cries were also cries of laughter. How she loved Simon! He knew it too.He writes her a check ordering her to buy something that doesn't make her look like a scrubwoman. "He went and kissed her on the braids, and she took his head and gave his kisses back two for one and with tremendous humor."
Next Augie goes to see Einhorn, who is recovering from a prostate operation and is complaining about the relationship of his son with Mimi Villars. Mimi and Arthur are living together while Arthur works on a book. She has tried to help him get a job, but Arthur is incapable of holding one. Augie also visits Manny Padilla, who is not sympathetic when he hears about Augie's experiences in Mexico: "Holy Christ, March, what did you have to go there for, with a broad like that and a bird!" Augie protests that he was in love, but Padilla replies, "Is love supposed to ruin you? It seems to me you shouldn't destroy yourself out of life for purposes of love -- or what good is it?"
Padilla diagnoses Augie's problem: "you're too ambitious. You want too much, and therefore if you miss out you blame yourself too hard." It's a familiar problem of Bellow's protagonists: Remember Henderson's "I want, I want" or Herzog's obsessions over Madeleine. Talking to Clem Tambow, Augie decides that his problem is his refusal to specialize: "Specialization was leaving the like of me behind. I didn't know spot-welding, I didn't know traffic management, I couldn't remove an appendix, or anything like that." Clem tells him, "You have ambitions. But you're ambitious in general. You're not concrete enough. You have to be concrete. Now Napoleon was. Goethe was."
"You can't adjust to the reality situation. I can see it all over you. You want there should be Man, with capital M, with great stature. As we've been pals since boyhood, I know you and what you think. Remember how you used to come to the house every day? But I know what you want. O paidea! O King David! O Plutarch and Seneca! O chivalry, O Abbot Suger! O Strozzi Palace, O Weimar! O Don Giovanni, O lineaments of gratified desire! O godlike man!"So far, Augie admits, he has found only one specialization: He trained a bird. "I always believed that for what I wanted there wasn't much hope if you had to be a specialist.... And besides specialization means difficulty, or what's there to be a specialist about? I had Padilla's slogan of 'Easy or not at all.'"
Mimi puts him on to a job opportunity that she had found for Arthur, but he doesn't want to be tied down by it: "there was a millionaire engaged in writing a book and he was looking for a research assistant." Augie needs the money: He has finally heard from Stella, but she tells him she is unable to repay his debt just yet -- she will when she finds a job, she promises. So Augie goes to see the millionaire, a man named Robey, who had been one of Frazer's students when Frazer was teaching. "Arthur said the book was to be a survey or history of human happiness from the standpoint of the rich." Augie is justifiably skeptical, but he doesn't want to be dependent on Simon, so he goes to see Robey.
The house sits on a lakefront, and is lavishly and eccentrically furnished. There is a portrait of Robey's mother, who "looked demented and wore a crown, a scepter in one hand and a rose in the other." Arthur has told Augie that she believed "she was the queen of Rockford, Illinois.... She had a throne. She expected everyone in town to bow to her." Though he is afflicted with a stammer, Robey rambles on about his plans for the book. "I thought, Oh, what a crazy bastard! What kind of screwloose millionaire have they sent me to?" But he decides to go through with it, and after some haggling gets Robey to agree to pay him thirty dollars a week for thirty hours work. "I was used to enthusiastic projects that would never leave the inventor's hangar. Like Einhorn's indexed Shakespeare back in the old days." (Or, he might have added, Thea's hunting trip.)
So he submits to Robey's reading assignments and twice-a-week conferences in which he reports on what he's read and answers Robey's questions. "In the autumn he lost his grip on himself. He went on giving me assignments and I collected my thirty bucks with a free conscience, but he didn't do any work." Robey comes to depend on Augie for some kind of stability. "But he gave me a rough time just the same. He was very sensitive and wanted my good opinion; however, he was extremely variable, humble one minute and making sure of his money's worth the next, or yelling or being sullen, sticking out his big red mouth in unhappiness or anger."
His even more eccentric sister, Caroline, also lives in the mansion. "She was screwy. And when she found I had been in Mexico she took a shine to me, believing herself Spanish." But Augie reflects, "I had taken care of my brother George. That ability or quality was with me yet, and sometimes people sensed it. Sometimes I wished I could become a shoemaker too."