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"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.
I suppose he'd had the name ready for a long time, even then. His parents were shiftless and unsuccessful farm people—his imagination had never really accepted them as his parents at all. The truth was that Jay Gatsby of West Egg, Long Island, sprang from his Platonic conception of himself. He was a son of God – a phrase which, if it means anything, means just that – and he must be about His Father's business, the service of a vast, vulgar, and meretricious beauty. So he invented just the sort of Jay Gatsby that a seventeen-year-old boy would be likely to invent, and to this conception he was faithful to the end. (6.6-7)
"Jay Gatsby" may be a deception in the eyes of the world, but to James Gatz, "Gatsby" is the truth about him. Is it really a lie if you believe it with all your heart?
"I found out what your 'drug-stores' were." He turned to us and spoke rapidly. "He and this Wolfsheim bought up a lot of side-street drug-stores here and in Chicago and sold grain alcohol over the counter. That's one of his little stunts. I picked him for a bootlegger the first time I saw him, and I wasn't far wrong."
"What about it?" said Gatsby politely. "I guess your friend Walter Chase wasn't too proud to come in on it." (7.284-85)
When he's caught lying, Gatsby doesn't care. As he sees it, everyone is engaged in some kind of deception, including Tom's friends. But Tom has different standards—double standards.