The Great Gatsby: Howard Da Silva as Meyer Wolfsheim

Howard Da Silva as Meyer Wolfsheim in The Great Gatsby (1974)


Howard Da Silva as Meyer Wolfsheim, legendary gambler

New York City, Summer 1925

Film: The Great Gatsby
Release Date: March 29, 1974
Director: Jack Clayton
Costume Designer: Theoni V. Aldredge


Though perhaps not as well known as his gangland contemporaries today, Prohibition-era racketeer Arnold Rothstein served as the basis for generations of fictional characters in pop culture for generations after his 1928 murder.

Born on this day in 1882, Rothstein began gambling at a young age, was reportedly a millionaire by the time he turned 30, and was most likely integral in the infamous “Black Sox Scandal” that accused eight members of the Chicago White Sox of throwing the 1919 World Series to the Cincinnati Reds.

It may be coincidence that the Volstead Act became official nationwide on his 38th birthday, a gift for the visionary Rothstein who has been considered among the first to recognize the business potential of Prohibition. He was one of the most influential figures in organized crime during the roaring ’20s, forging a bootlegging empire that included notable mobsters like Meyer Lansky, “Lucky” Luciano, and Dutch Schultz, many of whom looked up to Rothstein as a mentor.

Despite these dangerous connections, it’s likely that Rothstein met his early end due to nothing more nefarious than a poker game. After racking up a debt of more than $300,000 due to what Rothstein called a fixed game, the 46-year-old gangster was shot during a business meeting at the Park Central Hotel on November 4, 1928, dying two days later.

Though directly portrayed on screen by the likes of F. Murray Abraham (in the 1991 film Mobsters) and Michael Stuhlbarg (in the first four seasons of Boardwalk Empire), Rothstein’s legacy also includes a bevy of fictional characters that he inspired, including Nathan Detroit in the musical Guys and Dolls and Meyer Wolfsheim in F. Scott Fitzgerald’s novel The Great Gatsby, as most clearly suggested by an exchange that cites the real Rothstein’s arguably most infamous “achievement”.

“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.”

“Fixed the World’s Series?” I repeated.

The idea staggered me. I remembered of course that the World’s Series had been fixed in 1919 but if I had thought of it all I would have thought of it as a thing that merely happened, the end of some inevitable chain. It never occurred to me that one man could start to play with the faith of fifty million people—with the single-mindedness of a burglar blowing a safe.

“How did he happen to do that?” I asked after a minute.

“He just saw the opportunity.”

“Why isn’t he in jail?”

“They can’t get him, old sport. He’s a smart man.”

— The Great Gatsby, Chapter 4

A significant if briefly featured character in the novel, Wolfsheim never factored into any of the half-dozen major screen adaptations until 1974, when he was perfectly portrayed by stalwart stage and screen veteran Howard Da Silva.

Interestingly, one of Da Silva’s last roles before he was blacklisted during the HUAC witch-hunt of the ’50s was playing the simple-minded garage owner George Wilson in Elliott Nugent’s 1949 adaptation of The Great Gatsby. (Before Nugent took over, the film was to be directed by John Farrow… whose daughter Mia would portray Daisy Buchanan in the 1974 version!)

Howard Da Silva as George Wilson in The Great Gatsby (1949)

George Wilson (Howard Da Silva) guns down Jay Gatsby (Alan Ladd) in his swimming pool at the end of The Great Gatsby (1949).

Wolfsheim: I can’t forget, as long as I live, the night they shot Rosy Rosenthal there. It was six of us at the table, Rosy had eaten and drunk a lot the whole evening. The waiter came over to him with a funny look, said “somebody wants to talk to you outside.” “Alright,” said Rosy, he starts to get up. I pull him down in his seat. “Let the bastards come in here if they want you, don’t you—so help me—make a move out of this room.” Then it was four o’clock in the morning. If you raised the blinds, we could have seen daylight.
Nick: Did he go?
Wolfsheim: Sure he went. He turned in the doorway, he said “don’t let the waiter take away my coffee.” They were on the sidewalk, they shot him three times in the belly, they drove away. I understand you’re looking for a business connection, eh?

While we only get one scene with Da Silva’s Wolfsheim, he makes a memorable impression on the audiences—and Nick Carraway (Sam Waterston)—as he and Jay Gatsby (Robert Redford) reminisce about old times and departed acquaintances, suggesting that the mysterious millionaire Gatsby could count himself among the many protégés like Lansky and Luciano who benefited from the tutelage of a popular and powerful racketeer.

What’d He Wear?

Wolfsheim comments on the not insignificant age difference between himself and his two younger lunch companions, and indeed he dresses in a considerably more old-fashioned manner with his wing collar and a businesslike but unseasonal dark gray chalk-stripe flannel suit.

Robert Redford, Howard Da Silva, and Sam Waterston in The Great Gatsby (1974)

Wolfsheim: “This is a nice restaurant, but I like across the street better.”
Gatsby: “It’s too hot over there.”
Considering that Wolfsheim is wearing a dark flannel suit over an odd waistcoat in the middle of a hot New York summer, I would imagine the heat of “the old Metropole” wouldn’t bother him much, especially when it comes with his treasured memories of a friend getting shot to death a decade earlier.

The angles presented on screen never show Wolfsheim below knee level, so the most we see of his dark gray chalk-stripe flannel suit is the single-breasted jacket, which—like many of the other men’s costumes—reflect an interpretation of 1920s fashions through a ’70s-cut lens, with peak lapels and pocket flaps broader than an old-fashioned gent like Wolfsheim would have worn.

The wide, sharp peak lapels roll to a single button appropriately positioned at Howard Da Silva’s waist, with four matching but smaller buttons “kissing” on each cuff. In addition to the welted breast pocket, the ventless jacket has straight hip pockets with wide rectangular flaps.

Unlike the contemporary turndown collars of his younger dining companions, Wolfsheim wears a striped shirt with a detachable stiff white wing collar. The cotton shirt body is striped in alternating scarlet and slate pencil stripes, with white single cuffs that contrast against the rest of the shirt. Wolfsheim wears a black silk tie, detailed with a field of white woven pin-dots and knotted in a half-Windsor.

Howard Da Silva as Meyer Wolfsheim in The Great Gatsby (1974)

“I see you’re looking at my cuff buttons.”

I hadn’t been looking at them, but I did now. They were composed of oddly familiar pieces of ivory.

“Finest specimens of human molars,” he informed me.

“Well!” I inspected them. “That’s a very interesting idea.”

— The Great Gatsby, Chapter 4

After Wolfsheim departs, the naïve Nick Carraway asks Gatsby—with not inconsiderable optimism—whether or not their companion is a dentist, prompting Gatsby to inform him that he’s a gambler…and one with some questionable connections, at that. Though it’s never outwardly stated, I like the implication that the otherwise affable Wolfsheim wears human teeth for cuff links as a sinister reminder to acquaintances the fate that could befall them if they cross him. (Of course, it could just be that Wolfsheim has a friend like Walter Sobchak who “could get you a tooth by three o’clock this afternoon.”)

Wolfsheim wears his peculiarly periodontal cuff links through the shirt’s single cuffs, a dressier alternative to double (French) cuffs that was typically reserved for formal evening wear, i.e. white tie and tails, by the 1920s.

Howard Da Silva as Meyer Wolfsheim in The Great Gatsby (1974)

“Finest specimens of human molars” are the kind of cuff jewelry that will get new lunch companions wondering if you’re a dentist.

Wolfsheim’s odd waistcoat (vest) also marks a departure from Gatsby and Nick in their matching three-piece suits. Though the suit and waistcoat are both gray flannel, Wolfsheim wisely wears a waistcoat in a significantly lighter shade of gray that couldn’t be perceived as a poor attempt to match a non-matching fabric, instead presenting as tasteful while somewhat dandified. You can read more about the practice of wearing odd waistcoats at Bond Suits.

Wolfsheim’s lapeled waistcoat fastens high to mid-chest with six charcoal buttons that Wolfsheim wears correctly with the lowest button undone over the notched bottom. In the right pocket of his waistcoat, Wolfsheim carries a gold pocket watch, connected to a gold chain that loops “double Albert”-style through a hole adjacent the waistcoat’s third button.

Robert Redford and Howard Da Silva in The Great Gatsby (1974)

“Gatsby?” With one flash of his watch, Wolfsheim reminds his erstwhile protégé of a pressing call.

As Wolfsheim rises from the table, a waiter walks over with his hat and cane, a degree of service not afforded Gatsby, whose Panama hat joins those of fellow diners on a nearby rack. While the newer fedora style was gaining a foothold—or should I say headhold—among younger wearers through the 1920s, the traditional homburg with its “pencil curl” brim remained a a stalwart among distinguished wearers projecting an image of wealth and power… think the newly crowned Don Michael Corleone (Al Pacino) in The Godfather. Wolfsheim wears a dark gray felt homburg with a wide black grosgrain band.

Howard Da Silva as Meyer Wolfsheim in The Great Gatsby (1974)

“You’re very polite, but I belong to another generation,” Rothstein announces as he departs, illustrating the point with his homburg and cane. “You sit here and discuss your sports and your young ladies and your— as for me, I am sixty years old, and I won’t impose myself on you any longer.”

We can’t see Wolfsheim’s shoes, but a traditional choice for this outfit would be plain black leather oxfords. If he chose to lean into the image of an old-fashioned dandy, he may even dude up the shoes with a set of white spats, which I would have truly regretted not seen on screen.

How to Get the Look

Howard Da Silva as Meyer Wolfsheim in The Great Gatsby (1974)

Unlike his flashier dressed protégé Jay Gatsby who fashionably dresses for Jazz Age New York, Meyer Wolfsheim composes himself to old-fashioned perfection in shades of gray flannel with a wing collar and a degree of mystery that invites speculation… as wearing a set of teeth on your cuffs is wont to do.

  • Dark gray flannel chalk-stripe suit:
    • Single-breasted 1-button jacket with wide peak lapels, welted breast pocket, straight flapped hip pockets, 4-button “kissing” cuffs, and ventless back
    • Flat front trousers
  • Scarlet-and-slate pencil-striped white cotton shirt with detachable white wing collar and white single cuffs
    • Human molar cuff links(!)
  • Black silk tie with white pin-dots
  • Gray flannel single-breasted 6-button waistcoat with lapels, pockets, and notched bottom
  • Black leather oxford shoes
  • Dark gray felt homburg with black grosgrain band
  • Gold pocket watch on gold “double Albert” chain

Do Yourself a Favor and…

Check out the movie and read the original novel by F. Scott Fitzgerald.

You can also read more about the Rosenthal killing wistfully cited by Wolfsheim as an installment in Herbert Asbury’s sprawling chronicle Gangs of New York. If the name is familiar, this non-fiction volume would be partially adapted into a Martin Scorsese of the same name that starred Leonardo DiCaprio… who would later star as Gatsby in Baz Luhrmann’s 2013 adaptation of Fitzgerald’s novel!

The Quote

Known him? I made him!

One comment

Leave a Reply