Arnold Rothstein

Born in New York City in 1882, Arnold Rothstein was a businessman and kingpin of New York’s Jewish mob. He’s also legendary for trying to fix the 1919 World Series in what’s known as the Chicago Black Sox Scandal.
One thing that stands out about Rothstein, a.k.a. Big Al, is that he wasn’t just a brutal mob boss, but rather someone who understood the intricacies of business and ran the mob like a corporation.

“[He] had the most remarkable brain. He understood business instinctively, and I’m sure that if he’d been a legitimate financier he would have been just as rush as he became with his gambling and other rackets he ran,”

said Meyer Lansky, a.k.a. the Mob’s Accountant.
Thanks to his business acumen and mathematical brain, Rothstein accumulated a fortune worth an estimated $10 million, or approximately $140 million in when adjusted for inflation.
But long before he became New York’s richest and most important crime figure, Rothstein was a high school dropout trying to make his way through gambling.
That being said, let’s discuss Rothstein’s backstory, his gambling abilities, rise in the crime world, underground casinos, and demise – including how he was shot after a high stakes poker game.

From High School Dropout to Millionaire Gambler

Rothstein’s Early Knack for Gambling

Unlike many mob kingpins, who started out on the streets, Arnold Rothstein
was raised in an upper middle class family in Manhattan. His father, Abraham,
was a successful merchant whose honest reputation earned him the nickname “Abe
the Just.”

Arnold veered from this path early on since he got poor grades and was more
interested in gambling as a child. Math was the only school subject that
Rothstein excelled in, and it served him well in betting.

In a piece called Arnold Rothstein and the 1919 World Series Fix by Victoria
Vanderveer, he was asked when he became a gambler.

“I always gambled. I can’t remember when I didn’t,” Rothstein
responded. “Maybe I gambled just to show my father he couldn’t tell me what
to do, but I don’t think so. I think I gambled because I loved the excitement.”

Arnold resisted his father’s authority and resented the attention his parents
gave to his older brother, Harry, who was studying to become a rabbi. This is
one reason why Arnold refused to stop shooting dice after his father caught him
and scolded him for it.

Career as a Cigar Salesman

After dropping out of high school, Rothstein didn’t have the bankroll to
pursue his true passion of gambling.

This forced him to take up a career as a cigar salesman. But as Leo Katcher
describes in a biography on Rothstein called The Big Bank Roll, Arnold never
lost sight of his true goal.

“The cigar salesman made a good living. He lived frugally, did not
dissipate,” writes Katcher. “Each week the roll in his pocket grew a
little thicker. He knew he could never attain his ultimate aim by simple
economies, but these could start him on his way. He didn’t like long range
projects. He was essentially a short term, quick turnover man.”

Eventually, Rothstein sold enough cigars and saved enough money to accumulate
a $2,000 bankroll. Worth over $28,000 today, Arnold felt that he had enough to
become a professional gambler and quit his salesman job.

The Big Bankroll

It didn’t take Rothstein long to experience success in his new career as a
professional gambler. He was willing to bet on anything as long as he felt like
the odds were in his favor.

Rothstein’s ability to quickly calculate odds and work through complicated
math made him a fortune. And like a shark smelling blood in the water, Rothstein
would take advantage of any weak minded gamblers he came across.

“Look out for Number One. If you don’t, no one else will.” Rothstein said.
“If a man is dumb, someone is going to get the best of him, so why not you? If
you don’t, you’re as dumb as he is.”

The HBO show Boardwalk Empire portrays Rothstein as a patient man who was
willing to wait as long as it took to find a favorable opportunity.

“I’ve made my living, Mr. [Nucky] Thompson, in large part as a gambler,”
Rothstein said. “Some days I make 20 bets. Some days I make none. Weeks,
sometimes months in fact, when I make no bets at all because there simply is no
play. So I wait, plan, marshal my resources and when I finally see an
opportunity and there is a bet to make, I bet it all.”

Through his combination of patience and mathematical abilities, Rothstein
soon became a millionaire through gambling.

He carried large amounts of cash with him so that he could cover any
favorable bets that arose. Said to always have at least $20,000 cash on him,
Rothstein earned the nickname The Big Bankroll.

Rothstein Opens Casinos, Tries to Fix World Series

The Beginning of an Empire

By age 28, Rothstein moved to Manhattan’s Tenderloin district, which was
known for brothels, underground gambling, and corrupt officials.

Rothstein fit right in and quickly opened an underground casino in the
Tenderloin. The high end casino was a big success, generating over $10,000 a day
in the 1910s.

This allowed Arnold to continue investing in more casinos and brothels. He
also bought a large stake in a racetrack at Havre de Grace, Maryland, where he’s
believed to have fixed races and gained insider information.

Through a wide network of informants that he paid very well, Rothstein
received tips on horses and races that the average bettor didn’t have access to.

Fixing the 1919 World Sox

While never convicted, Rothstein is believed to have orchestrated the
infamous Black Sox Scandal of 1919, where Chicago White Sox players were paid to
throw the World Series.

When the heavily favored White Sox lost to the Cincinnati Reds 5 games to 3,
speculation became rampant that the mob boss fixed the Series.

One version of the story suggests that former bantam boxing champion Abe
Attell acted as a middleman between Rothstein and the White Sox players.

Another version claimed that gambler Joseph Sullivan approached Rothstein
about a scheme to fix the World Series. Arnold quickly rejected the offer, but
later reconsidered after hearing Attell’s proposal.

As writer Michael Alexander concludes, Rothstein thought that he could work
with both Sullivan and Attell while still covering his own involvement.

Whatever the case, Rothstein, now known as The Fixer, was called to testify
before a grand jury in Chicago. Arnold assumed the identity of an innocent
businessman, chastising the courtroom for viewing him with prejudice.

“Gentleman, what kind of courtesy is this? What kind of city is this?”
Rothstein questioned. “I came here voluntarily and what happens? A gang of thugs
bar my path with cameras as though I was a notorious person, a criminal even.”

Aside from lecturing the grand jury, Rothstein also said that he had nothing
to do with the Black Sox Scandal.

“The whole thing started when Attell and some other cheap gamblers
decided to frame the Series and make a killing,” Arnold told the courtroom. “The
world knows I was asked in on the deal and my friends know how I turned it down
flat. I don’t doubt that Attell used my name to put it over. That’s been done by
smarter men than Abe. But I was not in on it, would not have gone into it under
any circumstances and did not bet a cent on the Series after I found out what
was under way.”

It helped Rothstein’s cause when signed confessions by White Sox players
Eddie “Knuckles” Cicotte, “Shoeless” Joe Jackson, and Claude “Lefty” Williams
disappeared.

Katcher writes that the prosecution tried to get the players to repeat their
confessions on the stand, only to have them plead the Fifth Amendment.

With no confessions, the state didn’t have enough to indict Rothstein, and
they were forced to deny that he had any involvement with the scandal.

Arnold did admit that he won less than $100,000 from betting on the Reds, but
Katcher claims that the sum was actually $350,000.

Controversy over 1921 Travers Stakes

In addition to being accused of fixing horse races at his Maryland track,
Rothstein is also believed to have cheated at the 1921 Travers Stakes.

Owner of a racehorse named Sporting Blood, Rothstein allegedly paid trainer
Sam Hildreth to help him drive up Sporting Blood’s odds.

Hildreth entered a champion horse named Grey Lag, which pushed Sporting
Blood’s odds up to 3 1. Based on additional information that the horse with the
second best odds was off her feed, Rothstein bet $150,000 on Sporting Blood to
win.

Grey Lag was scratched from the race shortly after this, and Sporting Blood
went on to win, earning Rothstein a $450,000 profit. Much like the Black Sox
Scandal, nobody could prove that Rothstein did anything wrong.

Becoming a Kingpin

More Casinos and Racetracks

With the World Series case behind him, Rothstein continued to expand his
empire by opening more casinos, brothels, nightclubs, and racetracks.

The casinos were very successful because of how well the staff treated
gamblers.

“Treat the customer right. After all, he’s paying your salary,” Arnold
informed his staff. “His stupidity is our income. Even if the lush insults your
mother, let it go. He’ll come back to the tables, and then we take his money
with a smile.”

Prohibition

The year after the Black Sox Scandal, Prohibition began, which Big Al saw as
an excellent business opportunity.

Rothstein’s operation saw liquor smuggled from the Hudson River, Canada, and
across the Great Lakes. He also bought into speakeasies to capitalize on the
market.

Rothstein was one of the biggest bootleggers in the early days of
Prohibition. But he later slowed down in this space and began putting more
effort into dealing drugs.

Narcotics & Financing Other Gangsters

Partnering with Charles “Lucky” Luciano, Rothstein got more into drug dealing
in the mid 1920s. This industry became more lucrative for Arnold than
bootlegging, and he eventually financed other major mobsters in the narcotics
industry.

Famed gangsters under Rothstein’s hierarchy included Dutch Shultz, Frank
Costello, Jack “Legs” Diamond, Lansky, Luciano, Owney “The Killer” Madden, and
Waxey Gordon.

Big Al financially backed mobsters and provided other services, which
entitled him to 90 percent of the take from their operations.

“Rothstein’s main function though was organization,” writes Katcher. “He
provided money and manpower and protection. He arranged corruption for a price.
And, if things went wrong, Rothstein was ready to provide bail and attorneys. He
put crime on a corporate basis when the proceeds of crime became large enough to
warrant it.”

Gang Mediator

Also nicknamed The Judge, Rothstein served as a mediator between warring New
York gangs. Most of these mediations took place at a historic restaurant called
Lindy’s on Broadway and 49th Street.

It wasn’t cheap for gangs to have Rothstein mediate their differences. After
one dispute that he settled, Rothstein handed the gang leaders an invoice for
$500,000, which they paid.

Aside from settling mob disputes at Lindy’s, Rothstein also conducted many
other business matters in the place he called his “office.”

Surrounded by armed bodyguards, Big Al made bets, collected debts, and had
important meetings in the restaurant.

Bribing City Officials

Based on all of his criminal enterprises and gambling successes, Rothstein
had more money coming in than he could handle. So he began lending cash to
prominent city officials, politicians, police captains, and other authority
figures.

Rothstein wasn’t always concerned with getting the money back since he could
ask favors of anybody who didn’t repay debts. This helped him make indictments
and charges on his men disappear.

Poker Losses and Shooting Death

A Losing Streak

By 1928, Rothstein had accumulated enough wealth to own numerous businesses
on Broadway and in other parts of the city. But after so many years of success,
the 46 year old hit a major losing streak.

Not only did he lose hundreds of thousands of dollars at the racetrack, but
his businesses were faring worse.

While the losing streak wasn’t enough to cripple his net worth, Rothstein’s
confidence took a hit.

High Stakes Poker Game Gone Wrong

In September 1928, Rothstein played in a high stakes poker game involving
gambler Alvin “Titanic Thompson” Thomas, George “Hump” McManus, and Nate
Raymond.

Lasting 3 days, the poker game really took its toll on Rothstein, who lost
$320,000, or $4.5 million with inflation. Big Al refused to pay the debt because
he claimed that the game was fixed.

In the book Titanic Thompson, writer Kevin Cook backs Rothstein’s
assertion. Cook writes that Thompson fixed the game.

In the end, Rothstein not only owed $320,000 to Raymond, most of which went
to Thompson through a private agreement, but also $30,000 to Thompson and
$200,000 to other players. McManus is the only one who lost to Rothstein, owing
him $51,000.

Whether the game was fixed or not, Rothstein was viewed negatively by many
throughout the city for refusing to pay up.

At one point, Big Al claimed he would repay the debt after his $550,000 wager
on Herbert Hoover winning the presidency was determined.

Shooting & Death

On November 4, Rothstein was hanging out at Lindy’s when he received a call
to meet McManus at the Park Central Hotel on Seventh Avenue.

Nobody knows what was said during the call or why Arnold rushed to meet him.
It’s also unknown what happened to Rothstein once he arrived at the hotel and
met McManus.

Witnesses saw him stumble out of an elevator holding his stomach as he moved
out the door, where he collapsed from a gunshot wound.

While at Stuyvesant Polyclinic Hospital, police tried to get Rothstein to say
who shot him. But all they could get out of him was, “You stick to your
trade, I’ll stick to mine.”

Keeping true to the code of the gangster, Rothstein died on Nov. 6 along with
the name of the shooter.

Ironically, Arnold’s losing streak ended after he died, with Hoover being
elected the president.

Theories on Arnold Rothstein’s Death

Following Big Al’s death, police arrested McManus under the assumption that
he carried out the hit as a result of Rothstein’s poker debt.

McManus was arrested and tried, but later acquitted because the prosecution
didn’t have enough evidence. Thompson testified at McManus’ trial and described
him as a gracious loser who wouldn’t shoot anybody.

According to Cook’s book, Thompson told friends that it wasn’t McManus who
shot Rothstein, but rather Hyman Biller, who collected illicit money for
Thompson. Cook supports this theory by writing that Biller fled to Cuba after
Rothstein was shot.

One more theory is that Schultz had Arnold killed in retaliation to a turf
war involving Legs Diamond.

Shultz’s gang moved in on Diamond’s territory, which brought Rothstein into
the picture because he was financing Diamond at the time. Big Al had his
soldiers take out some of Schultz’s soldiers and business partners, including
Joe Noe.

Upset over the death of Noe, who helped Schultz in the beginning, he later
ordered McManus to carry out the hit.

This theory is supported by McManus calling Schultz’s attorney, Dixie Davis,
after the shooting. Following the call, Schultz’s men picked McManus up and he
was later acquitted of the murder charges.

Aftermath of Rothstein’s Death

After Rothstein died, the corporate structure that he’d established began to
crumble as street gangs fought for the liquor and narcotics markets.

Frank Erickson, Lansky, Bugsy Siegel, and other associates split up
Rothstein’s various operations.

Despite being worth millions at the time of his death, Rothstein’s money was
never found. His brother Harry searched for the remainder of his estate, but was
forced to declare Rothstein bankrupt 10 years later.

Rothstein Depicted in Popular Culture

Boardwalk Empire

Played by actor Michael Stuhlbarg, Rothstein is accurately portrayed as a New
York kingpin who does business with Atlantic City bootlegger Nucky Thompson,
played by Steve Buscemi.

Luciano, Lansky, and Bugsy Siegel work for Rothstein in the show.

The Great Gatsby

In this 1925 novel written by F. Scott Fitzgerald, Meyer Wolfsheim is based
on Rothstein. Wolfsheim is a famous gambler and Jewish mentor of Gatsby’s who’s
credited with fixing the World Series.

The Godfather Part II

In the 1974 film The Godfather Part II, Hyman Roth, who’s based on
Meyer Lansky, says that he admired Rothstein for fixing the World Series.

Vito Corleone, played by Marlon Brando, discusses how “Roth” worked closely
with his family during the Prohibition era. Rothstein was also a friend of Moe
Greene, who developed Las Vegas in the film.

Other Movies and Works

• Reporter Damon Runyon referred to Rothstein as “The Brain” and wrote
  about him in several short stories. One of them was The Brain Goes Home,
  which gave a fictionalized account of Rothstein’s death.
• Portrayed by Robert Lowery in the 1960 film The Rise and Fall of
  Legs Diamond.
• Portrayed by David Janssen in the 1961 movie King of the Roaring 20s – The Story of Arnold Rothstein.
• Portrayed by Michael Lerner in the 1988 sports film Eight Men Out.
• Portrayed by Murry Abraham in the 1991 movie Mobsters.

Conclusion

Arnold Rothstein represents one of the most impressive rises in mob history,
starting out as a high school dropout and ascending to become the kingpin of New
York City.

Gambling served as the original catalyst behind Rothstein’s rise, and he
accumulated a fortune through his uncanny mathematical ability.

As Lansky pointed out, Rothstein could’ve been successful in any business
pursuit. But he chose illicit means, including underground casinos, bordellos,
bootlegging, narcotics, bribing officials, fixing games / races, and extortion.

Based on his incredible wealth and connections to city officials, Big Al
could buy himself or any of his men out of trouble. He also brought a unique
corporate structure to organized crime that would be emulated for decades.

By the late 1920s, he was considered the most powerful man in New York. But
this same time period saw his empire come crashing down as he kept losing bets
and money through his businesses.

This included the poker game where Rothstein refused to pay a $320,000 debt,
claiming the game was fixed.

It’s unclear whether the poker game or his orders against Dutch Schultz’s
gang brought about his downfall. But on Nov. 4, 1928, Rothstein was hit with the
fatal bullet that would see him die two days later from the wound.

His fortune disappeared in the aftermath, and his empire was divided up among
associates.

While his estate may be gone, Big Al will always be remembered for his
alleged role in the 1919 World Series, and his considerable power throughout the
Roaring 20s.