Could Jay Gatsby afford his lavish parties on a bootlegger's income?
We don't know much of Gatsby's financial life, or even of his parties. All we know is what Nick Carraway tells us. And Nick only knows what Gatsby told him. And what Gatsby told Nick makes for good romance but bad financial planning: The parties were an extremely costly and extremely indirect approach to reconnecting with Daisy Buchanan.
But Gatsby was interested in Nick because he was interested in Daisy. And so his presentation to Nick was almost certainly influenced by his desire to win over an ally of Daisy's, and, eventually, Daisy herself. If we correct for that bias, a more reasonable picture of Gatsby's finances comes into view.
"I made the pleasure of [Gatbsy's] acquaintance just after the war," Meyer Wolfsheim tells Nick. "But I knew I had discovered a man of fine breeding after I talked with him an hour. I said to myself: 'There's the kind of man you'd like to take home and introduce to your mother and sister.' "
We don't know the full extent of Gatsby's involvement in Meyer's operations. But we know that Meyer's original interest in Gatsby was that he could serve as the Waspish, respectable front man for Meyer's operations.
The blond, apparently well-bred Gatsby could go where Meyer couldn't, slapping backs and throwing parties and calling people "old sport." Meyer needed somebody like that. "I saw right away he was a fine-appearing, gentlemanly young man, and when he told me he was an Oggsford I knew I could use him good," he says.
Roose's analysis assumes that Gatsby had a bootlegger's income. But Wolfsheim was into much more than that. He fixed the 1919 World Series, for instance. He has some sort of bond scam in the works. And we have to assume, I think, that Gatsby's home and his parties are, to a greater or lesser degree, a business expense for him. They're part of creating the Gatsby vehicle that can carry the Wolfsheim business.
Gatsby might say the parties and the house are all about Daisy. He might even mean it. But a man as serious about appearance and anonymity as Wolfsheim isn't going to let his front man hurt the brand on account of some old flame. If Wolfsheim was agreeing to these daily parties then he was probably financing them, too. The affairs might have been about Daisy for Gatsby, but they were probably about further penetrating New York's high society for Wolfsheim. It's possible, and perhaps even likely, that the parties weren't even Gatsby's idea. They might have simply been part of his job description.
Roose's accounting suggests that Gatsby was going into debt on the parties, or perhaps barely breaking even. But add in Wolfsheim as a partner and it's possible that Gatsby was doing just fine. Nick assumes Gatsby was paying to throw the parties, but perhaps Wolfsheim was paying Gatsby to host them.