When you first meet Meyer Wolfsheim in the basement of a New York City speakeasy, the air is thick with the smell of illegal gin and the weight of secrets. He’s a small man. Flat-nosed. He’s got these tiny eyes that scan the room like he’s constantly calculating the odds.
Honestly, most high school English classes treat him like a footnote. They mention the "human molar" cufflinks and move on. But if you really look at him, Meyer Wolfsheim in The Great Gatsby is the person who actually built the "Great" Gatsby.
Without him, Jay Gatsby is just James Gatz—a guy with a dream and an empty wallet.
The Real Man Behind the Molar Cufflinks
Fitzgerald didn't just pull this character out of thin air. Meyer Wolfsheim is based on Arnold Rothstein, the kingpin of the Jewish Mob in the 1920s. People called Rothstein "The Brain" or "The Big Bankroll."
He’s the guy who allegedly fixed the 1919 World Series.
When Gatsby tells Nick Carraway that Wolfsheim is the man who played with the faith of fifty million people, Nick is staggered. It’s one of those moments where the shiny, romantic veneer of the Jazz Age cracks. You realize Gatsby’s "new money" isn't coming from some vague business deal. It's coming from the darkest corners of the American underworld.
Why those cufflinks matter
Let's talk about the teeth.
Wolfsheim proudly shows off his cufflinks, which are made from "finest specimens of human molars." It’s grotesque. Most people think it’s just Fitzgerald being weird, but it’s a power move.
It tells you three things:
- He’s violent. You don't get a set of human teeth without someone losing them.
- He’s sentimental. He views these remnants of his enemies or associates as trophies.
- He’s untouchable. He can walk into a public space wearing evidence of a crime and nobody says a word.
Meyer Wolfsheim Great Gatsby: The "Gonnegtion"
Everything with Wolfsheim is about "gonnegtions." That’s how he says it. He’s the bridge between the legitimate world and the criminal one.
When Nick first meets him, Wolfsheim assumes Nick is looking for a "business gonnegtion." This is the core of Gatsby's wealth. While the book is a bit vague on the specifics, we know they were involved in bootlegging—selling grain alcohol over the counter in drugstores.
"I raised him up out of nothing"
After Gatsby dies, Wolfsheim is the one who tells the truth. He found Gatsby in a billiard room after the war, penniless and wearing his old uniform because he couldn't afford clothes.
Wolfsheim "made" him. He gave him his start.
This flips the whole "American Dream" narrative on its head. Usually, we think of the dream as hard work and grit. For Gatsby, the dream was a gift from a mobster. It wasn't about pulling yourself up by your bootstraps; it was about knowing the right gambler in a basement.
The Problem with the Portrayal
We have to address the elephant in the room. Fitzgerald’s description of Meyer Wolfsheim is deeply problematic.
He’s a caricature.
From the way his nose is described to his "Oggsford" accent, Fitzgerald leaned heavily into the antisemitic stereotypes of the 1920s. Critics like Richard Levy and Milton Hindus have pointed out that Wolfsheim represents the "outsider" who pollutes the "pure" American society.
It’s ironic because the "pure" society (the Buchanans) is actually way more corrupt and cruel than Wolfsheim ever is. Tom Buchanan is a racist and a bully. Daisy is a careless killer.
Wolfsheim, for all his crimes, actually seems to care about Gatsby in a weird way. He’s the only person who talks about "friendship" with any sincerity, even if he refuses to attend the funeral.
Why He Skips the Funeral
This is the part that always gets readers. Gatsby is dead. Nick goes to Wolfsheim’s office—the "Swastika Holding Company" (which, in 1925, was still a symbol of luck, though the irony is heavy today).
Nick begs him to come to the funeral.
Wolfsheim says no.
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He tells Nick: "Let us learn to show our friendship for a man when he is alive and not after he is dead."
Is it cold? Yeah. But it’s also practical. In Wolfsheim’s world, getting close to a murder investigation is a death sentence. He’s a survivor. He didn't get to be the man who fixed the World Series by being sentimental at funerals.
Key Takeaways for Your Next Reading
If you're writing an essay or just trying to sound smart at a book club, keep these points in mind:
- He is the architect: Gatsby didn't build his fortune; Wolfsheim did.
- The World Series link: Knowing the Rothstein connection makes the stakes feel much higher.
- The moral mirror: Wolfsheim is "honest" about his corruption, while the old money characters hide theirs behind social status.
- The survival instinct: His refusal to attend the funeral isn't just a lack of loyalty; it's a business decision.
Your next step is to look closer at Chapter 4 and Chapter 9. Compare the way Wolfsheim talks about Gatsby when he's alive versus when he's dead. Look for the "Swastika Holding Company" detail—it’s a jarring moment that changes how you view the "luck" of the 1920s. Pay attention to how Nick’s judgment of Wolfsheim shifts as he realizes just how deep the rabbit hole goes.