The Great Gatsby
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Proof of Gatsby's Criminality
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I hearitly agree with one exception to everything you have written. I don´t believe Jay to be the kingpin. Remember, it is Wolfsheim who brags to Nick that he has taken the Oggsford man under his wing. It is Wolfie who is calling the shots, Wolfie the head of the criminal network. Jay is but the first lieutenant, the front man. Jay is the spit and polish to Wolfie´s crudities, the all-American boy made to order for the fast crowd at Egg. The choice of domicile was more than likely twofold in that it satisfied both Wolfie´s and Jay`s needs-the one to market stolen highly priced items to the superwealthy crowd, the other to reintruduce himself to his long lost love.

Yes, "Kingpin" was a poor choice of words. I have replaced it with something less controversial, although I feel this to be a debatable issue. I vaguely remember at least one case where it seemed Wolfsheim was deferential toward Gatsby, or perhaps Gatsby seemed not to defer to him, making me question how much authority the older man had over him.
There were also at least two instances where Nick noticed on Gatsby's face a particularly hard look "as if he had just killed a man."
These are subtle indications that, taken together, could build a case that Gatsby was hardened enough to have outgrown Wolfsheim and was working more as a partner with him rather than a subordinate.
But I don't have the time at present to do the research to support "kingpin." Perhaps later...
Geoffrey: "the other to reintroduce himself to his long lost love."
I challenge anyone to support this assertion in the text. I have addressed it in detail elsewhere on Goodreads and repeat here again that the only possible textual source is Jordan's surmise to Nick after a conversation with Gatsby that he "half-expected" Daisy to show up at one of his parties. "Half-expected" is a far cry from Professor Bloom's "solely for the purpose of," which has been parroted endlessly by his academic minions,
On the basis Jordan's comment, Nick later romantically repeated the same supposition. There is no corroborating evidence presented to Nick (nor the reader)--no direct quote from Gatsby himself nor action he took--that supported Nick's imaginative conception of Gatsby's desire for Daisy being his sole or primary reason for throwing lavish parties at his mansion. It is all in Nick's head, and we know how obsessed Nick is with Gatsby from page one.
Nick exaggerated an offhand comment by Jordan into a romantic conception that has been passed along and embellished like parlor gossip into legend status by literary professionals because it fits a political objective--to make The Great Gatsby a celebration of capitalism and the American Dream, overshadowing the novel's warning about corruption.

I suspect that the two concocted a criminal plan to extend the network into a wealthy community in which they would sell stolen items only the rich would be able to afford. Bonds, jewelry, maybe even heroin and women would be the assets offered to the super wealthy. Jay tells Wolfie about this wonderful super rich community outside of NYC and our master criminal readily agrees considering its immense wealth.

Here 's the quote: (Ch. VII, p.103) [Nick narrating]
Then I turned back to Gatsby--and was startled at his expression. He looked--and this is said in all contempt for the babbled slander of his garden--as if he had "killed a man" for a moment that set of his face could be described in just that fantastic way.This is the fifth reference in the novel to Gatsby in the context of killing a man. The other four were rumors, but this time Nick actually witnesses the look on Gatsby's face that supports the rumors, as if to confirm or suggest to the reader that Gatsby's charisma concealed a sinister dark side that he kept well-hidden.
My impression is that the look was directed not at Nick but Tom, with whom he was arguing. In the Baz Lhurmann film, that "look" is directed at Tom as well. It is a malevolent gaze of intense hatred, well-portrayed by DiCaprio.
Anyone who's spent much time around someone with Borderline Personality Disorder, as I have, should be familiar with that look. These sociopaths often end up in prison, if they are male, or autocratic leaders of organizations, if female. (I am quoting here a passage from one three or four books I have read on Borderline Personality Disorder.) That murderous look can melt steel, and only a fool would disregard it.
Geoffrey wrote: "..seeking to renew a relationship with Daisy..."
I have yet to find anything in the text to support this other than a surmise by Jordan Baker to Nick after a conversation with Gatsby and Nicks subsequent exaggerated gossipy repetition of Jordan's guess, all of which is pretty weak. Gatsby did say that he'd read the papers hoping to see news about the Buchanans, but none of this is evidence that he chose a mansion across from Daisy's place or held lavish parties there in order to reconnect with her. I just don't see the evidence in the text.

So now your so called "gullible" Nick discerns that Jay had a "killer look". Which is it going to be?
Jordan´s statement is ample evidence that Jay planned his residence to fence Wolfies stolen goods. I don´t see why you so cavalierly disregard it. Consider that there were dozens of upscale communities throughout the USA at that time that he could have chosen to live in, why Egg? It´s simply too much synchronicity for me to believe otherwise.
I believe, as stated in a much earlier post, that there was general agreement between the two. Wolfie´s protege and polished first lieutenant was up to fencing stolen items in a wealthy community. Of course this is but conjecture, but considering that SF never clearly spelled out their relationship, we can only conjecture.
Considering that Wolsheim lived in Chicago it would be easier to sell the goods at another part of the country where local police would not be able to trace it. Considering that the FBI wasn´t the effective federal investigatory force it is today, it would be easier to escape detection. Remember that this was 2 years before JEdgar was appointed director of an unprofessional, fledgling organization.

As for murder in his past, that would have come up in Tom´s solicited detective report but never came up. That´s why I doubt that Jay murdered anyone. But yet Nick gives it enough credence to half believe it or he wouldn´t have written about those "looks". Which only goes to show how morally corrupt Nick is to be so partial to a master criminal.
Yes, Wolfie must have been quite a benefactor/mentor for Jay to become so hardened. From cavalier, serial philanderer to master criminal.
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A close reading shows that Jay Gatsby was a bootlegger and a major player in a scam to sell worthless bonds in small towns and gullible victims at his lavish parties. Indeed, the parties were designed for THIS purpose, NOT, as Bloom and his minions assert, "solely to attract Daisy," an assertion for which there is scant support in the text.
Evidence on the page:
A--Nick sells bonds for a living and Gatsby tries repeatedly to recruit him to join his team to peddle bonds that are apparently counterfeit or stolen.
B--Nick notices "well-dressed" Englishmen at the party whom Nick concludes are probably selling bonds.
C--The owl-eyed man reveals that most of the patrons at the parties were brought there, suggesting they were solicited.
D--Multiple references link Gatsby to organized crime via Chicago, a city notorious during the 1920s as Al Capone's headquarters. Gatsby is repeatedly interrupted to take or make telephone calls from/to Chicago, ostensibly to coordinate bond scam activities.
E--Nick intercepts a Chicago telephone call intended for Gatsby about someone named Parke getting apprehended (Ch. IX, p. 166) Nick, narrating: Proof is here revealed of Gatsby's involvement in a scam to sell stolen or counterfeit bonds.
Slagel, apparently Gatsby's underling, reports that a member of their sales team, Parke, has been captured by authorities while attempting to deliver illicit bonds in a small Midwestern town. "The numbers" refers to the list of serial numbers that would have been reported to authorities as stolen or counterfeit.
Here are the instances leading up to this condemning telephone conversation.
1--Ch. 1, p.3 (Nick, narrating): Nick sells bonds for a living, making him Gatsby's recruiting target (revealed later.)
2--Ch. 3, p.42 (Nick notices the sales team at the party, strongly suggesting that purpose of the parties was to attract the affluent targets for fleecing) Nick, narrating: Gatsby isn't throwing a party for strangers in the middle of a wealthy neighborhood just for the fun of it; he wants their money, and that's his sales team, cruising the crowd for suckers to buy his worthless bonds.
3--Ch. 3, p.44(The same scene, Nick and Jordan are in conversation with twins, one named Lucille.) Lucille speaks: This is the first of a string of five hints that Gatsby may have or was capable of killing someone, suggesting there is a sinister dark side to Jay Gatsby. The last of these (Ch. VII, p.103) [Nick narrating] is: This time it isn't a rumor. Nick actually witnesses the look on Gatsby's face, as if to confirm the rumors. My impression is that the look was directed at Tom, to send him a warning.
4--Ch. 3, p.46 (The owl-eyed man's revelation that "most people were brought.") Here's The owl-eyed man, addressing Nick and Jordan: Why pay to have people brought to a lavish party if you don't expect some benefit, such as the purchase of bonds by a liquored-up patron or two?
5--Ch. 3, p.48 (Just after Gatsby introduces himself to Nick, he excuses himself to take a call from Chicago.) Nick, narrating: The mention of Chicago foreshadows a connection between Gatsby and organized crime.
6--Ch. 4, p.71 (After introducing Nick to Wolfsheim, Gatsby excuses himself to make a phone call.) Nick, narrating: Why portray Gatsby as someone prone to telephone interruptions unless it's relevant to characterization or plot? He's not married, has no girlfriend of whom we're aware nor has he any children, whereas coordinating a field sales force would require frequent telephone contact.
7--Ch. IV, p.79 (The only reference in the entire book as to a purpose for the parties is an offhand speculation by Jordan on the last page of Chapter IV after her private conference with Gatsby.) Jordan: "I think" is a surmise, at best, and "half-expected" is anything but "solely" and a far cry from "hoped." This statement eliminates any romantic justification for the parties. If not for Daisy, what were they for? Taking into account the hints Fitzgerald has provided, bond peddling is the most likely reason.
8--Ch. V, pp.82-83 (Gatsby's first attempt to recruit Nick to sell bonds) Gatsby: Gatsby's attempt to recruit Nick to sell bonds for him fails.
9--Ch. 5, p.90 (While waiting for Daisy, Gatsby has been filling in some of his background and renews his recruitment offer to Nick.) Nick, narrating: Gatsby's second attempt to recruit Nick also fails.
10--Ch. V, p. 93 (Gatsby has been showing Daisy and Nick around his mansion.) Nick, narrating: Here Gatsby appears to be coordinating the activities of someone targeting a small town, like the one Parke gets nabbed in in Chapter IX.
11--Ch. VII, pp.133-134 (Nick, Jordan, Gatsby, Daisy and Tom are at the hotel, where Tom unmasks Gatsby as a criminal.) Tom (the ellipses are mine): Tom could only be referring to the sale of illicit bonds as revealed in the Chapter IX phone conversation with Slagel about Parke getting picked up.
12--Ch. VII, p. 134 (The same scene, just after Tom's comment above.) Nick, narrating: As foreshadowed by one of his party-goers and now in the face of Tom's righteous condemnation, Gatsby's criminal soul briefly appears through his glitzy social veneer. This spontaneous self-unmasking of his dark side by Gatsby is just what Daisy needs to make her decision to reject him, which she does a moment later.
13--Ch. IX, p.170 (When Nick visits Wolfsheim at "the Swastika Holding Company" to get him to attend Gatsby's funeral, four more rapid references are made to Chicago, again hinting at a link with organized crime.) Secretary (ellipses are mine): Like clanging a bell, Chicago is used throughout the novel as a symbol for organized crime.
In summary, Nick's observation of the sales team and the owl-eyed man's revelation that people were solicited for the parties suggests the parties were for selling bonds. If not, what was their purpose?
Nick sells bonds for a living. Gatsby tries to recruit him for this purpose. He takes frequent telephones calls as if coordinating sales activities, two of which are from Chicago, a notorious center for organized crime, and the climactic call from Chicago details the sale of illicit bonds in small towns.
In the hot Plaza Hotel room, Tom reveals that his investigation has uncovered some "new business" Gatsby's involved in that's much bigger than bootlegging, ostensibly the sale of illicit bonds.
Wolfsheim is linked to Chicago by the unnamed secretary's comments. Wolfsheim can't attend the funeral. He keeps a low profile, ostensibly because the FBI was known during the 1920s to attend funerals to link mobsters with their cohorts.
Fitzgerald provides the dots. It's up to the reader to connect them, but the evidence on the page proves the romantic tragedy is merely a frame within which to convey a stunning social critique of corruption, "the foul dust that follows in his [its] wake."
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