Chapter 4;

A notorious underworld figure, Wolfsheim is a business associate of Gatsby. He is deeply involved in organized crime, and even claims credit for fixing the 1919 World Series. His character, like Fitzgerald's view of the Roaring Twenties as a whole, is a curious mix of barbarism and refinement (his cuff links are made from human molars).

Mr. Wolfsheim recalls the past which seems to involve the underworld,

“The old Metropole,” brooded Mr. Wolfsheim gloomily. “Filled with faces dead and gone. Filled with friends gone now forever. I can’t forget so long as I live the night they shot Rosy Rosenthal there....(Chapter 4)