Throughout history, there have been renegades and rebels that seek to increase their wealth and earn respect through madness and chaos. They have been called by many names, like outlaws, bandits, or thieves, though most fall under the umbrella of “criminals”. Most criminals that faced off against the long arm of the law eventually felt the swift hand of justice. However, there were some clever devils who changed the very nature of what crime was and how it works. These guys were called gangsters.
When the world of sins and debauchery collected themselves under the highly lucrative business of organized crime, congregations of mobsters would strike together under the thumb of an often brilliant and always ruthless charismatic leader. We’re all familiar with organized crime - it’s what gave us the Godfather movies. However, there were a few charismatic leaders that gained unending notoriety. In the 1930s, just as the Great Depression reared its angry head, these criminal masterminds made themselves a reputation for ferocity that criminals today try, and luckily for all of us, fail to emulate. Their stories will leave you in equal parts awestruck and horrified!
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Born in 1882 as the son of an affluent and righteous Jewish businessman known by the nickname “Abe the Just”, Arnold Rothstein decided at a very young age not to follow in his father’s footsteps. He inherited his father’s intelligence and none of his conscience, taking to gambling as a child like a fish to water. All the scoldings in the world couldn’t stop him from rolling the dice - in fact, they often spurred him on!
Rothstein’s intelligence was off the charts, earning him the nickname “The Brain”. By the time he was 28, he had already established his own casino in New York and was heavily invested in a horse racing track, where his reputation for fixing outcomes first sprouted. He spent the next few years carefully building a network of spies, informants, and enforcers, making a fortune and reaching millionaire status by the age of 30.
He was among the first to exploit Prohibition for profit through bootlegging and black liquor sales. Despite a few brushes with the law on match-fixing charges among many other things, Rothstein never saw the inside of a jail cell (after witnesses and evidence always mysteriously disappeared).
By the time of his death in 1928, Rothstein had amassed the largest criminal organization in the country, filled with other notable gangsters like Lucky Luciano and Dutch Shultz. He died of a gunshot wound after a poker game went fatally wrong.
(By New York Police Department, Wikimedia Commons)
Charles “Lucky” Luciano, born Salvatore Luciano, was one of Rothstein’s many protegees, but a fearsome gangster in his own right, often referred to as the father of modern American organized crime. Born in Sicily, Italy, in 1892, Lucky and his family migrated to New York when he was 8 years old. When he was 14, he dropped out of school to take up a delivery job but was soon bitten by the gambling bug.
His initial years were spent as a low level but a quickly rising member of the Five Points Gang under the tutelage of older professionals like Rothstein, who taught him how to deal with everyone from members of high society to the lowliest of dealers and loan sharks. So it’s no wonder that he formed his own gang while he was still in his teens.
He had his fingers in every bowl he could find, from prostitution and gambling to drugs and the protection racket. As his gang and his mercilessness grew, he gained the reputation of wiping out his competition, i.e., other mob bosses, including some of his mentors. The 1930s saw Luciano engaged in a vicious gang war that ended with him at the head of the table.
His business ties extended beyond the American subcontinent to Mexico, Cuba, and even Italy. Despite facing numerous prosecution charges, Luciano never let go of his power and his thirst for it. Even during his brief stints in prison, he maintained control of his organization. Both his career and his life ended when he was 70, with a heart attack.
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Another one of Rothstein’s followers and also one of the competitors targeted by Luciano, Dutch Schultz came from modest beginnings and shot through the gang ranks like a bullet. Literally, in certain cases. Born Arthur Simon Flegenheimer to German Jewish immigrants in 1900, a 13-year-old Arthur left school to support his family after his father abandoned them.
Though he didn’t have quite the passion for gambling that Rothstein and Luciano did, he had a passion for money and knew that there was a lot of it in the gambling trade. Schultz's criminal career began with burglaries and robbed craps games, and after fleeing from the law, he found a new path to wealth during Prohibition. Working alongside notorious bootleggers, he became well-known for his uncontrolled temper and brutality.
While Luciano targeted competitors, Schultz was an emotional gangster who considered every murder he committed an act of retaliation. When Prohibition ended, Schultz switched games and joined the numbers game, an illegal gambling racket. It awarded him a pretty million dollars a month, affording him the perfect tax-free income.
In 1935, when a tax evasion case began to cut into his expensive tastes, Schultz murdered the lead prosecutor, against the wishes of the National Crime Syndicate. Lucky Luciano took this opportunity to take out Schultz with the blessings of other fellow mobsters.
(By Al Aumuller, Wikimedia Commons)
His birth name was Francesco Castiglia, but he is better known as “the Prime Minister of the Underworld”. An Italian born American growing up in East Harlem, New York, Costello joined his first gang when he was only 13 years old. He spent his formative years engaged in petty crimes and in and out of jail cells. That is until he met Lucky Luciano.
Their partnership started in 1918 and flourished during Prohibition, with the support and guidance of Rothstein. His bootlegging business was hugely successful as were all his attempts to escape any criminal charges levied against him. In the 1930s, when Lucky Luciano had wiped out his predecessors and taken over as head honcho, Costello was assigned his consigliere. He eventually found himself running the organization when both Luciano and his underboss Genovese were in prison.
Under the leadership of Costello, the business continued to flourish. He expanded his brainchildren, the bookkeeping, and slot machine operations and became one of the highest earners in Luciano’s organization. Costello’s influence over both mobsters and political figures grew until a large scale investigation by the US Senate resulted in Costello being stripped of his citizenship and much of the muscle in his crime family.
After barely surviving an assassination attempt by Genovese in 1957, Costello retired and handed over the business. He lived out the remainder of his life in his Waldorf penthouse, passing away from a heart attack in 1973.
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