“Start him! I made him.” … “ I raised him out of nothing, right out the gutter, I saw right away he was a fine-appearing gentlemanly young man, and when he told me he was an Oggsford man I knew I could use him good… (Pg 136, chapter 9)

This shows that Wolfshiem had introduced Gatsby to the profession of crime. Initially he had used Gatsby to do his dirty work for him. While working under Wolfshiem, Gatsby managed to work his way up to become a big “player” in the secret world of crimes. Wolfshiem essentially led Gatsby to a life of crime, which indirectly caused his death, and used Gatsby in his younger days to do work for him.

“Finest specimens of human molars” (Pg 57, chapter 4)

It implies that Wolshiem must have gotten those human teeth from someone whom he had inflicted harm upon. He might have beat someone up, his teeth fell out and he took them and made them into cuff buttons

“He’s the man who fixed the World’s Series back in 1919.” (Pg 58, chapter 4)

Solid evidence that Wolfshiem had been involved in criminal and illegal activities. This was match fixing on a large scale. In order for him to have gotten away with it, he must have had many connections with people or he
Wolfshiem really was a big criminal considering how important and big the world series was to the american society

“They’re some people Wolfshiem wanted to do something for. They’re all brothers and sisters. They used to run a small hotel.” (Pg 90, chapter 7)

Gatsby has fired all his servants and had replaced them with Wolfshiem’s people. You would think that people who ran a hotel, would know how to upkeep a house. Instead, Gatsby's house was a pigsty.
This leaves us to question the legitimacy of the hotel they were running. (Provided Gatsby was telling the truth, after all he is a mysterious man who has a lot of secrets) Nick also mentioned that one of Wolfshiem’s people had a “villainous” look. This also leaves us to suspect that Wolfshiem and his people were into shady illegal deeds and crimes.

“Gonnegtion”, “sid”, “ Oggsford”

Wolfshiem did not have a sophisticated manner of speaking, unlike Gatsby and the old money. Wolfshiem was wealthy, he was a part of the new money, and if he was not educated or from an old money background, it leads us to think that he obtained his wealth from criminal/illegal activities.

Wolfshiem is not seen as "rich" but more of a street gangster for the illegal goods that he provided. He is not accepted into the upper-class, the new rich or the old rich. He is in his own classification, the "gangster"

Chap 1:She was extended full length at her end of the divan, completely motionless...her chin raised a little, as if she were balancing something on it which was quite likely to fall.”

prefers to have privacy; links to fear of intimacy

Lied about many things, example, golf tournament, having engaged to another man

does not feel embarrassed about listening to other peoples privacy

Jordan appears distant, statuesque, and beautiful, even regal with her chin tilted into the air. Yet Nick’s description of her also appears with an air of fragility, as if she’s putting up a facade.

"I guess your friend Walter Chase wasn't too proud of to come in on it ." ..."Walter could have you up on the betting laws too, but Wolfshiem scared him into shutting his mouth" (Pg 106-107, Chapter 7)

Wolfshiem had exploited Walter Chase when he was at his lowest, when he had no money and was desperate to do anything just for a bit of money to keep him a float.

"Walter's afraid to tell me about" --> Gatsby had that look on his face, as if he had killed a man. This also shows that Gatsby and Wolfshiem had something violent and sinister going on. They might even have done something to Walter to make him keep his mouth shut about the horrendous crime they had committed. (Exploit Walter at his lowest+make him so scared that he doesn't even want to talk about it)

this shows the difference in their relationship as in chapter 9 she is spiting him and calling him careless.