Quote 1
"Meyer Wolfsheim? No, he's a gambler." Gatsby hesitated, then added coolly: "He's the man who fixed the World's Series back in 1919."
"Fixed the World's Series?" I repeated. […] "Why isn't he in jail?"
"They can't get him, old sport. He's a smart man." (112-118)
This New America may not have room for pure-hearted dreamers like Gatsby, but it certainly does have room for corrupt, smarty-pants criminals like Meyer Wolfsheim.
Quote 2
"If it wasn't for the mist we could see your home across the bay," said Gatsby. "You always have a green light that burns all night at the end of your dock." Daisy put her arm through his abruptly, but he seemed absorbed in what he had just said. Possibly it had occurred to him that the colossal significance of that light had now vanished forever. Compared to the great distance that had separated him from Daisy it had seemed very near to her, almost touching her. It had seemed as close as a star to the moon. Now it was again a green light on a dock. His count of enchanted objects had diminished by one. (5.121-122)
When Gatsby and Daisy finally get together, the dream vanishes. Does this mean that the American Dream has to stay forever a dream? That it loses its meaning if we actually achieve it—or that, once we achieve it, we find out that it wasn't so great to begin with?
Quote 3
"See!" he cried triumphantly. "It's a bona-fide piece of printed matter. It fooled me. This fella's a regular Belasco. It's a triumph. What thoroughness! What realism! Knew when to stop, too - didn't cut the pages. But what do you want? What do you expect?" (3.49-50)
Gatsby can buy the things that rich people have, but he can't buy the education or experience. But from what the owl-eyed man says, it doesn't sound like anyone else is reading them, either. (See "Gatsby's Books" for an explanation.)
Quote 4
"I thought you inherited your money."
"I did, old sport," he said automatically, "but I lost most of it in the big panic – the panic of the war."
I think he hardly knew what he was saying, for when I asked him what business he was in he answered, "That's my affair," before he realized that it wasn't the appropriate reply.
"Oh, I've been in several things," he corrected himself. "I was in the drug business and then I was in the oil business. But I'm not in either one now." (5.97-103)
Gatsby may lie a lot, but he's not very good at it—and that, in Nick's eyes, makes him more honest than half the fakers who come to his parties.
Quote 5
"I don't think she ever loved him." Gatsby turned around from a window and looked at me challengingly. "You must remember, old sport, she was very excited this afternoon. He told her those things in a way that frightened her – that made it look as if I was some kind of cheap sharper. And the result was she hardly knew what she was saying." (8.22)
Gatsby actually rewrites the past to make it look like his version of events. This is—we hate to say it—basically the equivalent of saying that "no" means "yes." In fact, for Daisy, no really does mean no this time.
Quote 6
"Yes," he said after a moment, "but of course I'll say I was. You see, when we left New York she was very nervous and she thought it would steady her to drive – and this woman rushed out at us just as we were passing a car coming the other way. It all happened in a minute, but it seemed to me that she wanted to speak to us, thought we were somebody she knew. Well, first Daisy turned away from the woman toward the other car, and then she lost her nerve and turned back. The second my hand reached the wheel I felt the shock – it must have killed her instantly." (7.396-398)
Gatsby immediately says that he'll take the blame. This is chivalry at work—great, right? Well, maybe, until you realize that it means women never having to take responsibility for their actions, and never having to grow up. Personally, we'll take the responsibility.