David Pietrusza. Rothstein: The Life, Times, and Murder of the Criminal Genius who Fixed the 1919 World Series. New York: Carroll and Graf, 2003. Print.

Baseball as a Way to God mentioned in passing a man who was a fixture of the New York sports betting scene in the first three decades of the twentieth century: Arnold Rothstein. That book said that Rothstein was an associate of Damon Runyon and the man on whom F. Scott Fitzgerald based the character of Meyer Wolfsheim in The Great Gatsby. I had to find out more about this guy, if for no other reason than to be able to teach Gatsby better. Rothstein is also the model for Nathan Detroit in Runyon’s Guys and Dolls and Armand Rosenthal in some of his short stories.

Arnold Rothstein does deserve the title of criminal mastermind. One of his handles was the Great Brain. He understood that the businessman wants to satisfy his customer. That is true today with cellphones and automobiles. But it is just as true with gambling, prostitution, illegal drugs, illegal alcohol, or fencing stolen goods. Rothstein knew how to keep the customers satisfied and the authorities at bay. Often the person in authority was his customer.

Pietrusza tells us that when New York Mayor “Gentleman” Jimmy Walker heard about Rothstein’s mortal wounding on November 4, 1928, he said, “That means trouble from here on in.” (14) Pietrusza demonstrates that that was no exaggeration. Rothstein was the man who kept the peace among criminal gangs. Rothstein was the man who directly or indirectly paid off most politicians, policemen, and judges. He kept newspaper reporters like Runyon apprised of what he thought they should know—and made sure they did not find out what he did not want them to know.

This book is a detailed biography of Rothstein, focusing on what we can learn about his criminal life and connections. It tells how he started out working in and setting up illegal casinos for wealthy New Yorkers. When the authorities started shuttering the casinos, he began floating casinos. Although he was known to rig betting—he was implicated in the 1919 World Series fix, after all—he emphasized honesty and a good product. If a gambler thought games were rigged or police might be tipped off, he’d go somewhere else. If a drinker thought his whiskey was diluted or dangerous, he’d buy from someone else in the future. Everyone trusted Rothstein.

Since he had many high rolling patrons, he was able to amass a fortune which he was happy to invest in both legal and illegal operations. He would be happy to lend money at twenty percent interest or lend for a share in the business. His other nickname was Big Bankroll.

Since many of his patrons were prominent businessmen and politicians, he was able to get favors done. He was arrested several times but never convicted. As in the World Series scandal, people might have been convicted or sanctioned, but there was never enough evidence to implicate Rothstein. And Rothstein was connected to most of the top organized criminals in New York that few people thought of crossing him. Though he was shot to death, it may have been an accident; it certainly was not a “hit.”

People often owed Rothstein money, but he was also careful to owe others money. If you had any hope of getting the money he owed you, you would not want anything to happen to him.

For a criminal, Rothstein was a man of vision. Two men in particular stand out as being protégés of his—Lucky Luciano and Meyer Lansky. Luciano credited Rothstein with showing him how to dress and behave so that he did not look or sound like a gangster. Rothstein gave Lansky the vision for organizing criminal enterprises.

When Prohibition was about to be enacted, Rothstein shared what a great opportunity that would be. He cautioned Lansky about doing what the lower class “Mustache Pete” criminals did—distilling their own product which at best would be diluted and at worst would be poisonous. No, he told him. Import alcohol from countries where it was legal and sell it at a premium unopened. This will attract wealthy customers who will become repeat customers. This is exactly what happened. Even today we think of the Roaring Twenties as an upper class phenomenon.

Rothstein seemed always ready to try something new. Smuggling liquor, though profitable, was a lot of trouble. Smuggling illegal drugs was safer. You could still obtain pure heroin, cocaine, and other opiates legally in Germany or France. Two steamer trunks full of drugs could net someone the same profit as a freighter full of booze—and you had much less overhead and fewer people to bribe. Rothstein can probably be credited with organizing or at least outlining the first modern model drug smuggling operation in North America. At the very least, he was present at the creation.

Rothstein himself never drank or used drugs. His one vice was gambling. But even then he usually did not bet unless he knew the odds were good. Sometimes he lost deliberately to keep himself from looking guilty in a fix; sometimes it was to keep a repeat customer from becoming disgruntled. So what was Arnold Rothstein—a.k.a. Meyer Wolfsheim, a.k.a. Nathan Detroit, a.k.a. Big Bankroll—doing in the 1919 World Series fix?

First, we have to understand that Pietrusza has a challenge because as a rule criminals did not leave a paper trail. Many times documents that were collected by the authorities as evidence got misplaced or lost by policemen, attorneys, or judges who were being paid off. (Pietrusza presents evidence on how prevalent this was). Even today, nearly 100 years later, rumors persist of a signed confession by Shoeless Joe Jackson that disappeared before he went on trial. Still, there is enough testimony and dot-connecting that Rothstein comes up with a pretty credible scenario. One which, the author believes, disproves the scenario of the most famous telling of the story, the 1963 book Eight Men Out. He calls it “such a well written book, that it’s easy to gloss over the inconsistencies.” (150)

It was not unusual that baseball games were occasionally fixed. There were even some rumors, for example, that the 1918 World Series had a few players who were bribed. Rothstein was friendly with the owners of the New York Giants and their Hall of Fame manager John McGraw. He also had connections with the Brooklyn Dodgers and New York Yankees. But in 1919 it appears as though the idea of fixing the World Series began with a gambling syndicate in St. Louis. It is one way to make a sure bet.

Getting other gambling operations in Iowa and Illinois involved, they had the connections to the teams and authorities to do it, but they needed money. When the underworld needed money, they turned to “Big Bankroll” Rothstein. Working through middlemen in the various cities, Rothstein was able to transmit money for bribes to baseball and government officials and for payoffs to the eight players on the White Sox. Rothstein made somewhere between $200,000 and $500,000 as his people placed bets on the Cincinnati Reds. To keep himself looking clean, he also bet $60,000 on the White Sox. People could say that he could not have had anything to do with the fix after losing that much. Keep in mind that a dollar back then was worth close to twenty times what it is worth today.

There are so many characters and so many little plots in Rothstein that it is honestly hard to keep track of them all. A prologue introduces the reader to over a hundred names. You check back if you lose track. It is the same method that some editions of long Russian novels use. An epilogue lists 105 people—many are from the prologue, but not all—and tells the reader what happened to them after Rothstein died.

From all these accumulated stories, we get a great insight into the New York criminal underworld in the first three decades of the twentieth century. Pietrusza uses many specific instances to make his point. His book is well documented. It is remarkable just how well connected Arnold Rothstein was. Here is one little example. Col. Levi Nutt, the man in charge of the Federal Narcotics Bureau in the 1920s had a son and a son-in-law who both had worked for Rothstein. So had the bureau’s chief narcotics agent in New York. (274)

These few little details just scratch the surface of the book. If nothing else, Rothstein does make us appreciate the milieu of The Great Gatsby and the character of Meyer Wolfsheim. First, one difference. In Gatsby, Wolfsheim is described as having an unusual accent. However, a newspaper article on Rothstein said that he had “the manners of an aristocrat and a rare and beautiful vocal inflection.” (291)

Still, there is little doubt that Rothstein, like Wolfsheim in the novel, was known as “the man who fixed the World Series back in 1919.” As Gatsby told Nick Carraway, they could not pin any crimes on him because “he is a smart man.” If Carraway’s landlord was the Great Gatsby, Rothstein was the Great Brain.

Gatsby tells us that Wolfsheim wore cufflinks made from human molars. That is strictly symbolic. Rothstein tried to be low-key in outward signs of wealth. Normally the only jewelry that he wore was a tie pin with a gem, no body parts.

(As an aside, the cuff link image becomes a subtle but pointed one in the Gatsby novel. The last time Nick Carraway sees Tom Buchanan, Tom goes into a jewelry store. Nick speculates that Tom is either buying a string of pearls or cuff links. Tom gave Daisy a lavish string of pearls as a wedding present, so here Nick is implying that Tom might have a new girlfriend now that Myrtle has been killed. The cuff links make us think of Wolfsheim’s creepy cuff links, suggesting that Buchanan is as much of a killer and no less evil with his “old” money than Wolfsheim is with his “nouveau” riches.)

According to Lucky Luciano, though Rothstein’s dress was understated, it was high quality. He bought bolts of silk cloth from French designer Amos Sulka and had his shirts made from them. (202) Jay Gatsby tells Daisy he gets his shirts from a buyer in Europe, and Daisy starts weeping because she “never saw such beautiful shirts.”

When Gatsby is stopped by a policeman for speeding, Gatsby shows him something, and the policeman salutes him respectfully and sends him on his way. Gatsby tells his passenger that the once did a favor for the commissioner. That is straight from the life of Rothstein. Pietrusza shows there were a number of police commissioners who Rothstein could get to look the other way. That was actually one of Mayor Walker’s real concerns when heard Rothstein was dying because the mayor appointed the commissioner and he knew what kind of man he had appointed.

Right after Gatsby is killed, Nick goes to Gatsby’s house and picks up the phone when it rings. The man on the other end begins talking about bonds and some problems with the serial numbers being identified. Without any context, these bonds could be either stolen or counterfeit. But Pietrusza tells us that after the Great War some thieves stole five million dollars worth of Liberty Bonds. Arnold Rothstein was suspected of being behind what some called the Big Bond Robbery. It is a good possibility that at the very least he fenced them. Not too many people besides Big Bankroll would have either the money or the nerve to buy such loot. He then likely had “his people” in various places sell or redeem the bonds.

That sounds like how Gatsby made at least some of his money—along with the drugs and alcohol he may have sold from his pharmacies. Pietrusza reminds us that addicting drugs had only been made illegal in 1914 so there were many people in the country who had become addicted, not just for a “high” but through using patent medicines that contained narcotics. And like Arnold Rothstein himself, the Big Bond Robbery would have been known to most readers in 1924 when Gatsby was published.

Rothstein used some of his money to invest in legitimate businesses and real estate. He owned some stables for race horses. By 1920 most of the hotels or apartment buildings where Rothstein had his floating casinos, poker games, and craps shoots were owned at least partly by him. When he lent money, he usually charged twenty percent interest, but many times he would forgo the interest for a piece of the investment or action that the loan was for. As anyone in a similar position, he owned a lot of property and businesses mostly fronted by various holding companies. One such company was Rothmere Mortgage. He called his stables Redstone, what the name Rothstein means in English.

In The Great Gatsby, we are told Wolfsheim’s outfit was called the Swastika Holding Company. This was published, of course, before the German National Socialist Party would be specifically identified with either anti-Semitism or the swastika symbol. It was actually another racketeer, a sometime associate of Rothstein’s named Larry Fay, who saw the swastika as a good luck symbol. He owned a fleet of taxis whose logo was the swastika. He also ran a few speakeasies; the first one he decorated with swastikas carved in the wood paneling. It is very likely that Scott and Zelda Fitzgerald occasionally patronized this club. Many New York readers in 1924 would have associated that symbol with the speakeasy.

For anyone interested in a nonfiction account of some of the origins of organized crime, or certainly anyone interested in The Great Gatsby or the Roaring Twenties, Rothstein will be great reading.

The book’s epilogue reminds us that even in the rackets there is the possibility of redemption. In 1941 at the age of sixty, former mayor Jimmy Walker repented of “many acts of my life” and devoted the last five years of his life to Christ. He said that “The glamour of other days I have found to be worthless tinsel, and all the allure of the world just so much seduction and deception.” (384)

Sounds like a theme to the novels of F. Scott Fitzgerald.