Study Guide for The Great Gatsby

By F. Scott Fitzgerald

Chapter 4 (65-85)

Bootleggers and Gamblers:

One of Gatsby's guests refers to him as a bootlegger: check out these links (from Jazz Age Culture, U. of Pittsburgh) to find out more about famous bootleggers of the 1920's. Organized Crime, Mafia and Gangsters: NYC Gangsters (John Jay College); How Prohibition backfired and gave America an era of gangsters and speakeasies (Guardian)

Legs Diamond (New York bootlegger)Arnold Rothstein
(The Man Who Fixed the 1919 World Series)

Gatsby's Guest List:

Consider the inventive names Fitzgerald devises for all of the guests he noted at Gatsby's parties that summer.

Can you tell anything from them about the difference between old and new money? (Who has moved into Gatsby's mansion uninvited?) (65-67)

Gatsby and Nick Drive to New York:

Note the details of the life history Gatsby tells Nick as they drive into New York. Which parts, if any, of the story do you believe to be true?  Why is Gatsby telling Nick this story? Does he expect Nick to believe it? (69-71)

"Well, I'm going to tell you something about my life," he interrupted."I don't want you to get a wrong idea of me from all these stories you hear."

So he was aware of the bizarre accusations that flavored conversation in his halls.

"I'll tell you God's truth." His right hand suddenly ordered divine retribution to stand by. "I am the son of some wealthy people in the Middle West--all dead now. I was brought up in America but educated at Oxford, because all my ancestors have been educated there for many years. It is a family tradition."

He looked at me sideways--and I knew why Jordan Baker had believed he was lying. He hurried the phrase "educated at Oxford," or swallowed it, or choked on it, as though it had bothered him before. And with this doubt, his whole statement fell to pieces, and I wondered if there wasn't something a little sinister about him, after all.

"What part of the Middle West?" I inquired casually.


"San Francisco."

"I see."

"My family all died and I came into a good deal of money."

His voice was solemn, as if the memory of that sudden extinction of a clan still haunted him. For a moment I suspected that he was pulling my leg, but a glance at him convinced me otherwise.

"After that I lived like a young rajah in all the capitals of Europe--Paris, Venice, Rome--collecting jewels, chiefly rubies, hunting big game, painting a little, things for myself only, and trying to forget something very sad that had happened to me long ago."

With an effort I managed to restrain my incredulous laughter. The very phrases were worn so threadbare that they evoked no image except that of a turbaned "character." leaking sawdust at every pore as he pursued a tiger through the Bois de Boulogne.

"Then came the war, old sport. It was a great relief, and I tried very hard to die, but I seemed to bear an enchanted life. I accepted a commission as first lieutenant when it began. In the Argonne Forest I took two machine-gun detachments so far forward that there was a half mile gap on either side of us where the infantry couldn't advance. We stayed there two days and two nights, a hundred and thirty men with sixteen Lewis guns, and when the infantry came up at last they found the insignia of three German divisions among the piles of dead. I was promoted to be a major, and every Allied government gave me a decoration--even Montenegro, little Montenegro down on the Adriatic Sea!"


Little Montenegro! He lifted up the words and nodded at them--with his smile. The smile comprehended Montenegro's troubled history and sympathized with the brave struggles of the Montenegrin people. It appreciated fully the chain of national circumstances which had elicited this tribute from Montenegro's warm little heart. My incredulity was submerged in fascination now; it was like skimming hastily through a dozen magazines.

He reached in his pocket, and a piece of metal, slung on a ribbon, fell into my palm.

"That's the one from Montenegro."

To my astonishment, the thing had an authentic look.

"Orderi di Danilo," ran the circular legend, "Montenegro, Nicolas Rex."

"Turn it."

"Major Jay Gatsby," I read, "For Valour Extraordinary."

"Here's another thing I always carry. A souvenir of Oxford days. It was taken in Trinity Quad--the man on my left is now the Earl of Dorcaster."

It was a photograph of half a dozen young men in blazers loafing in an archway through which were visible a host of spires. There was Gatsby, looking a little, not much, younger--with a cricket bat in his hand.

Then it was all true. I saw the skins of tigers flaming in his palace on the Grand Canal; I saw him opening a chest of rubies to ease, with their crimson-lighted depths, the gnawings of his broken heart.

"I'm going to make a big request of you to-day," he said, pocketing his souvenirs with satisfaction, "so I thought you ought to know something about me. I didn't want you to think I was just some nobody. You see, I usually find myself among strangers because I drift here and there trying to forget the sad thing that happened to me."

Note the description of New York as the two cross the Queensboro Bridge into Manhattan:

Over the great bridge, with the sunlight through the girders making a constant flicker upon the moving cars, with the city rising up across the river in white heaps and sugar lumps all built with a wish out of non-olfactory money. The city seen from the Queensboro Bridge is always the city seen for the first time, in its first wild promise of all the mystery and the beauty in the world. (73)

A View of the City from the Queensboro Bridge

Lunch with Meyer Wolfsheim:

What is Gatsby's association with Meyer Wolfsheim? How has this colorful Broadway character made his money? (What was his most famous scam?) (What are his cufflinks made out of?) Why is Gatsby showing Nick this facet of his character? Is this a character or a caricature? (73-78)

What does Gatsby do when he and Nick run into Tom Buchanan at the restaurant? (78)

Daisy Fay and Jay Gatsby Five Years Before:

What story about Gatsby and Daisy does Jordan tell Nick? (79-83) How has Fitzgerald drawn on and then altered the details of his own courtship of Zelda to suit his purpose in this novel?

Another wonderful Fitzgerald image: Daisy on the eve of her wedding, drunk in the bathtub, crumbling Gatsby's letter:

She began to cry--she cried and cried. I rushed out and found her mother's maid, and we locked the door and got her into a cold bath. She wouldn't let go of the letter. She took it into the tub with her and squeezed it up into a wet ball, and only let me leave it in the soap-dish when she saw that it was coming to pieces like snow. (81)

When did Tom start cheating on Daisy? (Note the violent way that the affair became public.)

A week after I left Santa Barbara Tom ran into a wagon on the Ventura road one night, and ripped a front wheel off his car. The girl who was with him got into the papers, too, because her arm was broken-- she was one of the chambermaids in the Santa Barbara Hotel. (83)

As Nick wanders through Central Park with Jordan, he hears some girls singing the lyrics of a hit song from 1922: 'The Sheik of Araby':

"I'm the Sheik of Araby.
Your love belongs to me.
At night when you're are asleep
Into your tent I'll creep----"

The Song comes from a hit film of the silent era, The Sheik which starred the greatest sex symbol of the twenties: Rudolf Valentino.

Rudolph Valentino in The Sheik (1921)

What is the single reason why Gatsby has made all the money, bought the mansion, thrown the parties, and befriended Nick? What is everything leading to?

  • What picture of Gatsby's character is beginning to emerge for Nick and for you as we learn more and more about him?