History's 15 Most Scandalous Bootleggers and Rum-Runners

Occasionally, the government of the United States of America makes mistakes, creating laws that provide organized crime with the ability to make an incredible amount of profit. Banning alcohol, a cultural staple of civilized society for thousands of years, will likely be remembered as one of those errors. With the ratifying of the Volstead Act, which was vetoed by President Taft, gangsters, organized criminals and gentlemen made billions giving the people what they want: booze in defiance of prohibition. The intensity of the violence that resulted from the bootlegging and rum-running scene darkened the already bleak world of crime and fascinated audiences through countless movie and television documentaries, such as The Untouchables, Boardwalk Empire and Scarface: Shame of a Nation.

Despite the typical portrayal of bootleggers and rum runners as violent gangsters, prohibition was so unpopular that otherwise respectful and non-violent citizens developed their own distilleries or engaged in minor acts of smuggling booze. The level of corruption - political and otherwise - spawned by the flood of illicit money penetrated the most prestigious institutions of the United States of America. The following fifteen bootleggers and rum-runners are among the most famous, successful and notorious of the era and hailed from diverse nationalities, backgrounds and social circles.

Though many met with a violent, untimely demise, some managed to escape with little consequence to live lavish lifestyles.

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15 Arnold “The Brain” Rothstein

Arnold Rothstein was considered the smartest of all gangsters and bootleggers and was among the first to import liquor from England for illegal distribution in the United States. Son of successful businessman Abraham Rothstein – ironically known as “Abe the Just” - Arnold was the defacto leader of the Jewish underworld in New York, reaching out to cultivate criminal talent such as Lucky Luciano and Dutch Schultz, whom “The Brain” recruited from the minors to star in the big show.

Rothstein's influence even extended to major sporting institutions. Although never proven in a court of law, Rothstein and his associates were involved in rigging the 1921 Travers Stakes and the 1919 World Series, famously known as the Black Sox Scandal. Both events netted him large wagering windfalls and he prospered until he was shot by another, less successful gambler.

14 Al Capone

One of the most feared and famous bootlegging gangsters was Al Capone, who rose within his gang to eventually become a boss when his mentor and former leader, Johnny Torrio, was badly injured during an attack in 1925.

Despite the overwhelming violence and brutality he used to secure his power in the Chicago mob scene, the crime that finally nailed Capone and put him in jail for over seven years was tax evasion. Syphilis and his time in prison deteriorated his mental faculties, and he died in 1947 due to a stroke and pneumonia.

13 Dutch Schultz

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Born in 1902 as Arthur Flegenheimer, his family abandoned by his father when he was a teen, Dutch Schultz changed his name to a more threatening moniker and turned to crime when he discovered that it paid better than legitimate employment. Rum-running and bootlegging activities during prohibition helped make him loads of cash, along with his propensity to kidnap, torture and murder anyone who stood in his way. He died in 1935 when violence was turned on him, instead of his adversaries.

12 Charles “Lucky” Luciano

Born in Sicily in 1897 under the alias Salvatore Lucania before adopting his American name of Charles “Lucky” Luciano, Lucky started his criminal career in the schoolyard, mercilessly beating classmates who didn't pay him protection money.

After surviving numerous threats, Lucky applied what he learned in grade school to eventually become a crime boss, earning absurd amounts of cash through bootleg alcohol and other criminal activities. His stroke of genius was to streamline criminal organizations into a cooperative entity, focusing on money rather than killing each other, thereby empowering organized crime.

11 Joseph P. Kennedy

Although never verified as participating in the rum-running spree that took place after the Volstead Act, it's been rumored that the patriarch of the Kennedy clan derived some of his wealth from illicit alcohol.

Bootlegging would have simply added to his already considerable fortune, much of which was derived from stock manipulation and insider trading.

10 Bugsy Siegel

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Bugsy Siegel grew his criminal syndicate through gambling, bootlegging and assassinations, eventually teaming up with Meyer Lansky to create Murder, Inc. - a cadre of professional hitmen who weren't actually incorporated. He was one of the four assassins who took out Joe “the Boss” Masseria, further solidifying his power and reputation.

The cash he hustled turned into an ostentatious lifestyle, before he inexplicably decided to betray all the east coast mobsters at once by stealing millions earmarked for the Flamingo Hotel and Casino. He was promptly murdered with bullets in 1947.

9 Meyer Lansky

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As an associate of Arnold Rothstein, Lucky Luciano and Bugsy Siegel, Meyer Lansky started his criminal empire with gambling and auto theft before diversifying into illegal liquor, narcotics, extortion and prostitution. He eventually moved his money into legitimate businesses like casinos, golf courses and meat-packing.

Although his lifetime earnings were estimated at $300,000,000, perhaps Rothstein's greatest achievement was becoming an elderly gangster, dying of lung cancer at the age of 80.

8 Jack "Legs" Diamond

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Another contemporary and ally of Arnold Rothstein, Jack “Legs” Diamond, née Jack Moran, was born into an Irish family in Philadelphia before moving to Brooklyn after his mother's death.

He avoided poverty through theft and street crime before diversifying into the world of bootlegging. Rumor has it that he earned his nickname due to his dancing skills, though it was likely the former skills which led to his murder in 1931!

7 Dean O'Banion (a.k.a. Dion O'Bannion)

The main rival of Al Capone and Johnny Torrio was Dean O'Banion's crew, who controlled a significant amount of turf in Chicago. In addition to bootlegging, violence, theft and extortion, O'Banion ran a flower shop and made a killing off of gangster funerals.

When Capone and Torrio decided to eliminate the competition, they orchestrated his death in 1924, setting off a wave of gangland killings that lasted years.

6 George “Bugs” Moran

via Wikipedia.org

Bugs Moran was Dean O'Banion's second-in-command and childhood friend. As BFFs, they loomed large in Chicago's gangland scene as murderous bootleggers who controlled a large swath of territory. When Dean O'Banion was killed, Bugs became co-boss along with Earl “Hymie” Weiss.

When Earl Weiss was killed, Bugs took over until the Valentine's Day Massacre in 1929. Bugs escaped the killing, thinking Al Capone's men were police conducting a raid, allowing him to die in prison of lung cancer in 1957.

5 Johnny Torrio

Born in Italy, Torrio arrived in New York after his father died, eventually establishing one of the first modern organized crime groups in the United States. He got into bootlegging after unleashing the awesome violence of Al Capone against Big Jim Colosimo, allowing Torrio to take over the criminal empire, which included the unholy trinity of gambling, rum-running and brothels. Johnny also worked with Meyer Lansky, Lucky Luciano and real estate. Another rare example of an elderly gangster, he died at the age of 75 while chilling out in a barber's chair.

4 George Remus

via denofgeek.us

As a lawyer and a “pharmacist”, George Remus used his intimate knowledge of the Volstead Act to acquire large amounts of alcohol for medicinal purposes before losing the shipments, which seemed to reappear in speakeasies and illegal manufacturing facilities. Estimates suggest he made $40 million over the span of three years of bootlegging, allowing him to bribe the entire population of the United States of America simultaneously.

His legal expertise help set the standard for the stereotype of sleazy defense lawyers, when he successfully defended himself for murdering his wife in cold blood and in front of witnesses, claiming temporary insanity while avoiding being institutionalised because prosecutors stated he was sane enough to stand trial.

3 Lee Petty

via stockcar.racersreunion.com

Lee Petty was an expert at vehicular evasion while running rum and on bootlegging missions around the southern states. He eventually used his driving skills and expertise to become one of the first heroes of NASCAR, establishing a family tradition of racing dominance that includes Richard Petty's 200 wins and seven championships.

2 Enoch L. “Nucky” Johnson

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Subject of the HBO series Boardwalk Empire, Nucky Johnson ran Atlantic City back when it was considered cool to visit the state of New Jersey for leisure purposes. In addition to fostering bootlegging activities that kept bars, clubs and casinos wet, Enoch Johnson put the “pub” in “Republican” by controlling the activities of the political party through various back-channels.

1 William “Bill” McCoy

As an expert boat builder and master navigator of sea vessels, William McCoy looked at the rum-running scene and decided to change it up, taking a classy approach to his foray into crime. He only stocked the finest spirits, never diluted and always dealt fairly. He also designed superboats for millionaires and had a giant machine gun that fired only warning shots. After serving his time in jail for his activities, he retired and lived off the cash he made, never returning to crime.

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