Gatsby Is a Sinister Gangster (ex. Gatsby as Gangster)
by Thomas H. Pauly

In an article entitled “The Passing of the Gangster,” published in the March 1925 issue of American Mercury, Herbert Asbury confidently offered the remarkable assertion: “There are now no more gangs in New York and no gangsters in the sense that the newspapers use the word.” The surprising disparity between this contemporary evaluation of the crime scene and our perception of the 1920s as the heyday of gangsters hinges upon Asbury’s belief that the gangsters of his age owed their notoriety to ambitious journalists, novelists, playwrights, and scriptwriters fiercely competing for audiences and paychecks. Asbury viewed these accounts as distortions of truth in support of a threadbare stereotype. “The moving picture and the stage,” he pointed out, “have always portrayed the gangster as a low-browed person with an evilly glinting eye, a plaid cap drawn down over beetling brows and a swagger that in itself is enough to inform the world that here is a man bent on devilment.” With obviouscontempt, he counters: “In the main, the really dangerous gangster, the killer, was apt to be something of a dandy.” Asbury invoked his stylish gangster to return enthusiasts for these fictions to the hard fact that truly successful gangsters didn’t make brazen displays of their intent.

A “Dandy” New Type of Gangster

Even though his article shrewdly appealed to the same interest in gangsters he was criticizing, Asbury little suspected that his revisionist proposal would be quickly embraced. Unwittingly his “dandy” anticipated the innovative gangster which F. Scott Fitzgerald introduced a few weeks later with the publication of The Great Gatsby. Jay Gatsby effectively overturned the dated assumption that gangsters were lowlifes from the Bowery and replaced it with an upscale figure who was enviably wealthy and fashionably stylish. Significantly, this portrayal was an outgrowth of actual changes in existing criminal conditions. Fitzgerald understood better than Asbury that since the advent of Prohibition, gangsters were, in fact, on the rise; not only were they gaining more wealth and power, but they were presuming to status and respectability as well. If Fitzgerald’s Gatsby was solidly grounded in these historical developments, he too came perilously close to being an implausible gangster and a distortion of fact. Though readers still find Gatsby too romantic, too idealistic, and too naive to be a criminal success, Fitzgerald counteracted this impression by cloaking his gangster in mystery, then frustrating Nick’s efforts to penetrate it, and finally suggesting that Gatsby, like Asbury’s dandy, may be more dangerous than Nick realizes. If this elusive figure involved a significant modification of the actual gangsters on which Fitzgerald was drawing, he was not the specious fabrication that Asbury was decrying. To characterize Gatsby as a “dandy” might seem inappropriate since clothing is rather incidental to his depiction. This quality is communicated to Nick more by his other possessions than by his white suit, silver shirt, and gold tie—his palatial house, his grand parties, his fancy automobile, his hydroplane, and his library of real books. His flourish of expensive shirts late in the novel merely embellishes this image. This Gatsby is an ideal consumer in his expenditure of so much on the nonessential. Heis a dandy who buys expensive merchandise to take on its desirability and to convince Daisy of his worthiness. These traits confirm the potency of a consumer culture and illuminate the social instability generated by the age’s myriad products and aggressive advertising. The new credit economy of the 1920s accelerated social mobility and empowered a new ethos whereby merchandise rivaled background, profession, and merit as a determinant of status.

All around him Fitzgerald beheld people who had risen from commonplace backgrounds to affluence and prominence. His own success as a writer validated this new upward mobility. Still, the advances of gangsters were truly extraordinary. In 1920 George Remus was a small-time criminal lawyer who purchased a distillery for medicinal spirits in order to circumvent the recently passed Volstead Act. Though today’s readers are often confused by the connection between Gatsby’s bootlegging and his drugstores, Fitzgerald was merely registering the widespread exploitation of pharmacies’ exemption from Prohibition law due to the large quantities of alcohol used in their prescriptions. Remus’ success was to make drug stores as well known for alcohol as speakeasies. Within four years, he controlled fourteen distilleries, a sprawling network of pharmacies and some 3,000 employees. He had cornered one-seventh of the national market for medicinal alcohol and realized a gross income of some $25 million. His accumulated holdings were estimated at $40 million

Arnold Rothstein

Arnold Rothstein afforded another example of gangster wealth with a stronger, more direct influence upon Fitzgerald’s novel. In a letter written in 1937, in which he reflected on The Great Gatsby, Fitzgerald wrote: “I selected the stuff to fit a given mood or ’hauntedness’ or whatever you might call it, rejecting in advance in Gatsby, for instance, all of the ordinary material for Long Island, bit crooks, adultery theme and always starting from the small focal point that impressed me—my own meeting with Arnold Rothstein for instance.” Just prior to World War I, Rothstein was a smalltime gambler whose livelihood was jeopardized by the reckless actions of his hot-headed friend Herman Rosenthal. This crucial turning point in Rothstein’s career is referred to in the initial conversation between Nick and Meyer Wolfsheim:

“What place is that?” I asked.

“The old Metropole.”

“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. It was six of us at the table, and Rosy had eat and drunk a lot all evening. When it was almost morning the waiter came up to him with a funny look and says somebody wants to speak to him outside. ’All right,’ says Rosy… 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.”

“Four of them were electrocuted,” I said, remembering.

“Five, with Becker.” His nostrils turned to me in an interested way.

The wave of reform set off by these events propelled Rothstein to close his modest gambling parlor and initiate a system of floating games like those memorialized in [the musical and movie] Guys and Dolls. When Rothstein returned to a permanent facility several years later, he relocated outside the city, first with an elegant casino created from a Long Island estate and then with the “Brook” in Saratoga, which, at the time of its opening in 1919, was the most luxurious gaming house in the country. Meanwhile Rothstein’s diversification into sports betting climaxed with his reputed fixing of the 1919 World Series. For Fitzgerald and most Americans at the time, this was a breathtaking exemplification of Rothstein’s power. As Nick explains:

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 at 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.

Though Rothstein was to reap handsome profits from Prohibition, his emergence during the 1920s as the most important underworld figure in New York City owed more to an involvement with stolen bonds like the ones Gatsby is peddling at the time of his death. During the same year as the World Series fix, Jules “Nicky” Arnstein, a long-time gambling friend of Rothstein’s, stole some $5 million worth of Liberty bonds from vulnerable errand boys relaying them between brokerage houses and banks. Since these losses were covered by surety companies and Rothstein’s experience with bail bonding provided him with an insider’s knowledge of these companies, Rothstein may have provided Arnstein with confidential knowledge about these transfers. Whether or not he actually alerted Arnstein to this prospect, he quickly sprang to Arnstein’s defense when a minor criminal fingered him as the one responsible for these thefts. Significantly, these bonds were never recovered; meanwhile Liberty bonds played a role in several important Rothstein deals. Rothstein’s take from these bonds vastly exceeded his return from the fixed Series and was perhaps his single most lucrative venture. Indeed, Tom Buchanan’s sources appear most reliable in his characterization of Gatsby’s drug store chain as “just small change” compared to his stolen bonds…

Gatsby: A Fine Front

Readers are led to believe that Gatsby’s wealth derives from serving as a front of respectability for Meyer Wolfsheim, a “man bent on devilment” who badly needs someone to mask his blatant criminality… Unlike the Waspish Gatsby, whose smile of greeting warmly acknowledges Nick, this “small flat-nosed Jew … with two fine growths of hair which luxuriated in either nostril” ignores him and continues with his account of a recent payoff. He only responds to Nick when he shows knowledge of the Rosenthal affair. Wolfsheim’s one effort to engage Nick consists of calling attention to himself and pointing out how his cuff links are made of human molars. His ensuing characterization of Gatsby as “a perfect gentleman,” a “man of fine breeding” who went to “Oggsford College,” suggests the propriety Wolfsheim seeks from Gatsby while simultaneously establishing his distance from it. Nick’s account implies that Wolfsheim owes his success more to a brazen disregard for the law than any perceptive reading of character or subtle scheming.

The implication of Wolfsheim’s example—that most gangsters are obtuse, intractable lowlifes—is further reinforced by the phone call that Nick intercepts following Gatsby’s death. Without ever confirming that he is speaking to Gatsby, the caller blurts out how his disposal of the stolen bonds has miscarried. His characterization of Chicago as a “hick town” by way of justification only confirms his ignorance and incompetence.

Alongside these figures, Gatsby almost succeeds at being the possessor of manners and refinement he strives to appear, so much so that he comes across as a rather implausible gangster. Those same qualities which differentiate Gatsby from his criminal associates threaten his believability as the effective gangster he is supposed to be—unless, of course, there is more to Gatsby than his ungangsterish appearance and manner. Critics usually assume that Fitzgerald channeled the model of Arnold Rothstein into his characterization of Meyer Wolfsheim. While it is true that Wolfsheim is identified as the man who fixed the 1919 World Series, it is alsotrue that Gatsby was associated with the stolen bonds that were more crucial to Rothstein’s successful career. The presumed linkage of Wolfsheim and Rothstein also disregards the significant fact that the crude Wolfsheim was nothing like the actual Rothstein, who was something of a Gatsby to those who knew him. Ironically, Rothstein’s skills at engineering social mobility so far surpassed those of Gatsby that he would have had no need for him.

When he served as Fitzgerald’s inspiration, Rothstein was a man of enormous experience and sophistication. His early success at high-stakes gambling came from considerable intelligence and chameleon-like adjustment to the conditions of his profession. Well before he opened his own gambling parlor, he acquired the dress and demeanor of a man about town and successfully won the confidence of the well-to-do who made his games profitable. If the decidedly conservative cast of Rothstein’s dress, deportment, and choice of residences belied his aggressive pursuit of money and useful connections, it was cultivated not just to suggest well-heeled respectability but even more to avoid the kind of attention that… Remus so hungrily sought

The Paradoxical Heart of Gatsby’s Character

Although Rothstein differed from Gatsby in his metropolitan background, his more refined tastes, his vast network of criminal associates, and his calloused selfishness, he was that paradoxical blend of gentleman “dandy” and criminal success at the heart of Gatsby’s characterization. This aspect of Rothstein draws attention to a frequently overlooked aspect of Fitzgerald’s presentation, Gatsby’s evasiveness. Given all the confusion created by Gatsby’s “old sport” affectation, his indirect mode of communication, alongside all that is not known about him, Gatsby probably practices the same deception which made Rothstein so successful. At issue here is the central question of Gatsby’s function as a front. Manyreaders, like Nick, tend to assume that Gatsby’s wealth derives from facilitating a necessary liaison between the crude Wolfsheim and the proprieties of respectable society. Presumably Gatsby handles all public relations for the alcohol and stolen bonds that Wolfsheim supplies. This unexamined assumption never considers that behind his shaky facade of Waspish gentility Gatsby would have needed to be a more cunning criminal than Nick allows to have amassed so much wealth. Obviously a good front doesn’t just look impressive— he capitalizes on his impressiveness to gain the confidence of his victims and to mask his crafty maneuvering.

Artist that he was, Fitzgerald was sufficiently concerned about Gatsby’s implausibility as a gangster and his own limited knowledge of underworld operations that he made a concerted effort to obscure the course of events that transformed his innocent product of midwestern morality into a big time metropolitan gangster. Throughout the first half of the book, much of what the reader learns about Gatsby’s background is a crazy-quilt collection of rumors whose sum result is confusion and unbelievability. Gatsby is said to have been a German spy, to have gone to Oxford, and to have killed a man. His house and parties establish that he is very rich and cause him to be known by people from every level of society. However, few have actually met him and fewer have any reliable knowledge about the sources of his vast wealth. None of the many guests at his party can identify him. Significantly, the dust cover of the original edition of the novel accentuated this obscurity: “It is the story of Jay Gatsby who came so mysteriously to West Egg.” Reviewers of the novel noticed as well; the Saturday Review, for example, noted “all the cleverness of his [Gatsby’s] hinted nefarious proceedings” and suggested that “the mystery of Gatsby is a mystery saliently characteristic of this age in America.”

Nick’s Take on Gatsby

Much of the success of these jumbled suggestions derives from Fitzgerald’s use of Nick Carraway as a narrator who struggles to make sense of his confusing neighbor. Fitzgerald adds to the mystery surrounding Gatsby by first making Nick an outsider who learns about Gatsby as he is generally known (or not known). As he registers these baffling shreds of information, he naturally struggles to make sense of them. Meanwhile Fitzgerald teases his curiosity, along with that of the reader, by allowing him limited contact with Gatsby. The result of these suspect bits of information and brief glimpses is at best an impression.

Fitzgerald characterizes Nick as a person more intent upon learning than deciding. As he says in the novel’s introductory paragraphs, accentuating his mediation in our understanding of Gatsby, “I’m inclined to reserve all judgements.” … In sharp contrast to Gatsby, Nick comes from a very proper background that has carried him from Yale to the respectable but unprofitable career of a bond salesman. His inside knowledge of Eastern society and its mores enables him to see Gatsby for the “roughneck” he is. At the same time, his growing reservations about this society set off a reaction that invests Gatsby with greater significance and greater worth. “I wanted the world to be in uniform and at a sort of moral attention forever,” he admits in a frequently cited comment. Not unsurprisingly, this longing for a world that is pure and decent makes him acutely aware of the ways in which it isn’t. Troubled by his age’s award of respectability to the Buchanans and wealth to gangsters, Nick can’t help admiring Gatsby’s resolute commitment to success, love, and dreams. This Gatsby evidences traits which Nick deeply respects but finds sorely lacking in everyone else around him. Measured by this bias, Gatsby’s excesses and unbelievability validate his reassuring uniqueness.

Ultimately Nick does pass judgement without ever reckoning with these biases. In spite of Gatsby’s extensive involvement with crime, Nick arrives at the startling conclusion that he is essentially an innocent victim of other people’s heartlessness, a true believer destroyed by the cynicism of his age. “You’re worth the whole damn bunch put together,” Nick tells Gatsby at his last meeting, in a comment that vents his mounting disillusionment with his own social circle. Later he stamps out the obscene desecration scrawled on the steps of Gatsby’s empty house and offers his final association of Gatsby with the original beholder of the new world he imagines. Even though Gatsby’s loss of Daisy and ensuing death confirm Nick’s worst fears, he concludes that Gatsby “turned out all right at the end” because his death saved him from the demoralizing disillusionment that haunts Nick’s consciousness.

Hints About Gatsby’s Sinister Side

Because Nick’s estimate of Gatsby stems from such limited understanding of Gatsby and absorbs so many concerns peculiar to himself, one cannot help wondering if the man at the center of the mystery is really the one he finds. The novel offers at least one telling suggestion that Nick may have overlooked qualities that would make Gatsby more sinister than he has allowed. Nick shows surprisingly little reaction to Tom’s revelation of Gatsby’s involvement with stolen bonds and to the phone call following Gatsby’s death that reveals how his plans for disposing of them have miscarried. To the extent that he makes anything of these revelations, they reinforce his belief that Gatsby’s death saved him from having to face his across-the-board defeat.

True as this may be, Nick never suspects that Gatsby’s elaborate plans may have involved using him as an agent for his bonds. After all, Nick is a bond salesman. Moreover, he is too trusting and uncritical to question Gatsby’s persistent offers of help. “I’m going to make a big request of you today,” Gatsby explains before he takes Nick to meet Wolfsheim, “so I thought you ought to know something about me. I didn’t want you to think I was just some nobody.” Nick decides that Gatsby’s objective will be fulfilled when he later learns about the undisclosed “matter” from Jordan. Consequently, he is confused by Wolfsheim’s assumption that he is seeking “a business gonnegtion.” It never occurs to him that Gatsby, like the reader, might have perceived Nick’s uneasiness with Wolfsheim and thus squelched part of his plan with his hurried dismissal of Wolfsheim’s comment as a “mistake.” That Gatsby may have been cultivating Nick as a possible outlet for his bonds is made even more likely in his later remarks on the eve of his meeting with Daisy.

“Why, I thought—why, look here, old sport, you don’t make much money, do you?”

“Not very much.”

This seemed to reassure him and he continued more confidently.

“I thought you didn’t, if you’ll pardon my—you see, I carry on a little business on the side, a sort of side line, you understand. And 1 thought that if you don’t make very much— You’re selling bonds, aren’t you, old sport?”

“Trying to.”

“Well, this would interest you. It wouldn’t take up much of your time and you might pick up a nice bit of money. It happens to be a rather confidential sort of thing.”

For the reader bothered by Nick’s retreat from his ingrained skepticism in the case of Gatsby, this man of mystery seems more scheming and duplicitous than Nick acknowledges, if only because Gatsby’s extravagant possessions attest so eloquently to his success with crime. Nick simply cannot conceive that Gatsby would exploit others to achieve his objectives—nor that Nick’s own innocence and propriety might have carried Gatsby elsewhere to dispose of his bonds. The Great Gatsby poses a central question: Is Gatsby, as Nick assumes, one of the last romantics wholly dedicated to the love of his life, or is he perhaps, as Nick never really considers, a devious criminal who pursues his business with the same evasion and intrigue shown in his plotted reunion with Daisy? Of course, it is quite possible that he could be both. To see Gatsby as both lover and gangster would demand that this figure be recognized as having more in common with both the criminal Meyer Wolfsheim and the conniving Arnold Rothstein than Nick ever allows. Fitzgerald encourages his reader to consider this possibility. Although this Gatsby is as obsessed with the girl of his dreams as Nick believes, he also appears to be someone who is more intent upon his own objectives and more manipulative than Nick comprehends. This Gatsby is at once more sinister and more believably unbelievable, a true product of Prohibition’s criminal conditions.

Published in Studies in American Fiction magazine vol. 21, no. 2 (Autumn 1993) - except. Text scanned from Readings on "The Great Gatsby", ed. by Katie DeKoster (San Diego: Greenhaven, 1998).