He’s shady, sentimental, and possesses cufflinks made of human molars.
Meyer Wolfsheim is one of F. Scott Fitzgerald’s most unforgettable minor characters in The Great Gatsby.
As Jay Gatsby’s business associate and the man rumored to have fixed the 1919 World Series, Wolfsheim represents the dark, criminal underworld tethered to Gatsby’s immense fortune. His appearances offer unsettling glimpses into the true source of Gatsby’s wealth and the era’s pervasive corruption.
These 9 dark Meyer Wolfsheim quotes with page numbers (Scribner 2020 ed.) reveal his unique blend of brutality, nostalgia, and cynical pragmatism.
First Impressions: Sentimentality and Sinister Undertones
When Nick Carraway meets Wolfsheim over lunch, he encounters a peculiar mix: a man prone to nostalgic reminiscence about violent past events, simultaneously assessing Nick for potential business while sporting grotesque jewelry.
“— So I took one look at him,” said Mr. Wolfsheim, shaking my hand earnestly, “and what do you think I did?” … “I handed the money to Katspaugh and I sid: ‘all right, Katspaugh, don’t pay him a penny till he shuts his mouth.’ He shut it then and there.”
(Speaker: Meyer Wolfsheim to Nick Carraway, Chapter 4, Pages 69-70)
Wolfsheim immediately launches into an anecdote showcasing his shrewdness and power within his world. His forceful instruction to Katspaugh (“don’t pay him a penny till he shuts his mouth”) establishes his intimidating presence and pragmatic approach to dealing with perceived threats or loose talk.
“This is a nice restaurant here,” said Mr. Wolfsheim… “But I like across the street better!” … “Hot and small — yes,” said Mr. Wolfsheim, “but full of memories.”
(Speaker: Meyer Wolfsheim, Chapter 4, Page 70)
Wolfsheim expresses a preference based not on quality (“nice restaurant here”) but on nostalgia (“full of memories”). This hints at a sentimental side tied to places associated with his past, even if that past involves criminal activity.
“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…”
(Speaker: Meyer Wolfsheim, Chapter 4, Page 70)
His reminiscence about the Metropole reveals a morbid sentimentality. Wolfsheim appears genuinely affected by the loss of past associates (“faces dead and gone”), specifically the violent murder of gangster Rosy Rosenthal, blurring the line between friendship and criminal enterprise.
“Sure he went.” Mr. Wolfsheim’s nose flashed at me indignantly. “He turned around in the door and says: ‘Don’t let that waiter take away my coffee!’ Then he went out on the sidewalk, and they shot him three times in his full belly and drove away.”
(Speaker: Meyer Wolfsheim recounting Rosy Rosenthal’s murder, Chapter 4, Page 71)
Wolfsheim recounts Rosenthal’s murder with a striking blend of indignation (at Nick’s perceived naivete) and matter-of-fact brutality. The casual detailing of the shooting (“shot him three times in his full belly”) exposes his chilling familiarity with violence.
“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.’.” He paused. “I see you’re looking at my cuff buttons.” … ‘Finest specimens of human molars,’ he informed me.
(Speaker: Meyer Wolfsheim about Jay Gatsby, Chapter 4, Page 72)
This passage encapsulates Wolfsheim’s bizarre contradictions. He praises Gatsby’s “fine breeding” using sentimental language, then immediately undercuts this by revealing his grotesque cufflinks made of human teeth—a jarring symbol of the violence underlying his world.
Wolfsheim’s primary narrative function is to ground Gatsby’s mysterious wealth in the illicit realities of the Prohibition era and reveal Gatsby’s ascent from “the gutter.”
The “Gonnegtion”: Business, Corruption, and Gatsby’s Origins
Wolfsheim represents the hidden engine powering Gatsby’s dream. His brief appearances expose the likely criminal enterprises funding Gatsby’s lavish lifestyle and hint at Gatsby’s manufactured persona.
“Five, with Becker.” His nostrils turned to me in an interested way. “I understand you’re looking for a business gonnegtion.”
(Speaker: Meyer Wolfsheim to Nick Carraway, Chapter 4, Page 71)
Immediately after discussing electrocutions, Wolfsheim pivots to business. His assumption that Nick seeks a potentially illicit “gonnegtion” reveals Wolfsheim’s worldview, where opportunity and criminality are closely intertwined.
“Meyer Wolfsheim? No, he’s a gambler.” Gatsby hesitated, then added coolly: “He’s the man who fixed the World’s Series back in 1919.”
(Speaker: Jay Gatsby about Meyer Wolfsheim, Chapter 4, Page 73)
Gatsby’s casual reveal of Wolfsheim’s most notorious act—fixing the World Series—confirms his associate’s deep involvement in high-stakes crime. This information irrevocably taints Gatsby’s wealth by association, linking it to large-scale corruption.
“Start him! I made him.” … “I raised him up out of nothing, right out of the gutter. 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.”
(Speaker: Meyer Wolfsheim about Jay Gatsby, Chapter 9, Page 171)
Wolfsheim proudly claims responsibility for Gatsby’s success (“I made him”). His language (“raised him up out of the gutter,” “knew I could use him good”) frames Gatsby’s ascent not as an American Dream achieved, but as Wolfsheim recognizing and exploiting useful potential for his ends.
Discover more about Gatsby’s carefully crafted persona.
Despite his boasts of loyalty and creation, Wolfsheim ultimately prioritizes self-preservation, offering a final, cynical perspective on the nature of friendship in his world.
Final Reflections: Loyalty, Legacy, and Letting Go
After Gatsby’s death, Wolfsheim embodies a cold pragmatism. His refusal to attend the funeral, contrasted with his earlier claims of closeness, provides a final, stark insight into his character and the transactional nature of his relationships.
“Let us learn to show our friendship for a man when he is alive and not after he is dead.”
(Speaker: Meyer Wolfsheim, Chapter 9, Page 172)
Wolfsheim delivers this cynical wisdom as justification for abandoning Gatsby in death. It reveals his core philosophy: relationships are valuable only for their present utility, and loyalty does not extend beyond the grave or into inconvenient circumstances.
Conclusion: The Shadowy Architect
Meyer Wolfsheim, though appearing briefly, casts a long shadow over The Great Gatsby.
He’s the tangible link between Gatsby’s glittering dream and the murky underworld that financed it. A figure of strange contradictions—sentimental yet brutal, proud of Gatsby yet eventually abandoning him—Wolfsheim embodies the corruption and moral ambiguity festering beneath the surface of the Jazz Age.
His memorable words and actions, from molar cufflinks to fixing baseball’s greatest contest, are chilling reminders of the often-unseen forces shaping the pursuit of the American Dream.
His character deepens Fitzgerald’s critique, exposing the often-illicit foundations upon which great fortunes, and perhaps great illusions, are built.
Gain a complete view of the novel’s intricate world: explore our full collection of 79 revealing quotes from The Great Gatsby.
A Note on Page Numbers & Edition:
Like Wolfsheim’s shadowy connections, page numbers for The Great Gatsby can differ across editions! We referenced these page numbers from the authoritative The Great Gatsby: The Only Authorized Edition (Scribner, November 17, 2020), ISBN-13: 978-1982149482. Always consult your specific copy to ensure accuracy.
Jeremy Mortis, founder of Ageless Investing, applies a rigorous analytical approach (the AAM framework) to distill timeless wisdom and contextualized quotes from classic literature, saving you time while deepening understanding. Learn more about Jeremy’s unique background and methodology on his author bio page.