Being a gangster is more than just wearing a fancy suit and flashing the cash. The movies might have you believing that a gangster’s lifestyle is one that they happen to fall into by chance – they’re just good guys that have taken the wrong path.
In some cases, this may be true, but in reality the title of ‘gangster’ is usually awarded to people that have done some pretty horrendous things in their time. You don’t just wake up deciding you’re a gangster – your reputation makes you one.
Over the course of history, there have been numerous figures that have captured public interest. These are the people that make up the dark underbelly of society that most of us don’t see. Gambling rings, protection rackets, brothels, security fraud – it’s all there, we just don’t always know it. Sometimes these activities are hidden behind legitimate businesses, other times they are hidden in plain sight.
Behind all of these enterprises, there are the people that run things. Although underworld crime may not be as prominent as it once was, history can’t be erased. From murder to bank robbery, shoot-outs and drug trafficking, here are the 25 most notorious gangsters of all time.
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25. JACK “LEGS” DIAMOND
Jack “Legs” Diamond, also known as Gentleman Jack, was born in Philadelphia in 1897. Diamond was a bootlegger during the famous prohibition era. Growing up in Brooklyn, Diamond started out as a bodyguard for notorious gangster Arnold Rothstein. It was his duty to oversee the illegal sale of alcohol in Manhattan and he often kidnapped and tortured business rivals. He was also shot several times himself in various assassination attempts. In 1931, his enemies finally succeeded, shooting him in the head three times while he slept. He had just been acquitted of kidnapping charges. Although the murderers were never formally identified, it’s believed that it was Albany police themselves that took out the hit. Two years later, his widow was shot and killed in her Brooklyn apartment. It was speculated that this was to stop her from sharing any secrets.
24. THE KRAY TWINS
Two of the most famous gangsters ever known, London born twins Ronnie and Reggie Kray secured themselves a place in pop culture history. In the 1950’s and 1960’s, they were heads of an organisation dubbed ‘The Firm.’ The atrocities they committed were endless – from armed robberies and murders to arson and protection rackets. As nightclub owners, they became celebrities that were both feared and strangely admired. Although they managed to hide most of their illegal activity behind the guise of a legal business, things fell apart when they brutally stabbed and murdered a member of their own firm. A lot of their own people turned against them, for fear of what would happen to them. In March 1969 both twins were imprisoned for life. Ronnie was declared insane in 1979 and spent the remainder of his life in Broadmoor Hospital where he died in 1995. Reggie died of cancer in 2000.
23. JAMES BURKE
James Burke, otherwise known as ‘Jimmy the Gent’, was an American gangster with known links to the Lucchese crime family. You might recognize the name from the 1990’s hit film Goodfellas. In the 50’s, Burke was relatively a small timer, dealing with untaxed cigarettes and liquor, although it quickly escalated to large scale heists. He is said to be behind the Lufthansa Heist, where around $5.875 million dollars was stolen in cash from JFK International Airport. The aftermath of the heist has been described by gang member turned informant, Henry Hill, in various books. According to Hill, Burke became so paranoid after the robbery that he killed everyone involved. There was never enough evidence to charge Burke with the robbery so it went unsolved. He died in 1996 whilst serving life for the murder of con man Richard Eaton.
22. VITO GENOVESE
Italian born mobster Vito Genovese came to prominence as long-time friend and associate of Charles Luciano. Genovese was at the core of Mafia crime in America and lead Luciano’s crime family for 12 years. Because of this, it was later renamed the Genovese crime family. Together with Luciano, they operated a lucrative heroin trade, as well as other crime rackets. Due to some heat from the murder of mobster Ferdinand Boccia, Genovese moved back to Italy and became a lead Mafia figure there. After a brief stint in the U.S army, he was accused of the Boccia murder but acquitted due to lack of evidence. He re-joined his Mafia family in New York and carried on committing atrocious crimes, until he was arrested for drug charges. He was sentenced to 20 years and died on Valentine’s Day, 1969 of a heart attack.
21. JACQUES MESRINE
Jacques Mesrine was also known as ‘The Man of a Thousand Faces’. He was a master of disguise and managed to escape from prison several times. The French born criminal had a penchant for bank robberies and kidnappings in both his home country and Canada. After committing several robberies in France, he went on the run to Quebec where he worked odd jobs for a time. A dispute with a gardener lead to attempted kidnapping. Mesrine and his girlfriend were both sentenced to ten years in prison but escaped twice. They attempted to plan a mass break out which ended in a shootout. It didn’t stop there and the trail of murder continued until he was imprisoned in France – and he escaped again. A manhunt ensued and he was ambushed on the outskirts of Paris. He was shot fifteen times before being shot in the head with a pistol.
20. JAMES ‘WHITEY’ BULGER
James ‘Whitey’ Bulger was on the FBI’s Most Wanted list for 12 years before being captured in 2011. Bulger was an Irish-American crime boss of the Winter Hill Gang in Boston. Bulger’s crimes are too many to count – murder, drug trafficking, links to the IRA. In 1994, the DEA launched an investigation into Bulger’s activities. Gradually, bookmakers who were subject to a protection racket ran by Bulger began to testify against him. Due to close personal links with the FBI, Bulger was tipped off and fled Boston. He grew tired of life on the run and according to his replacement Boss, Kevin Weeks, he would have rather gone out in a blaze of glory than spend the rest of his life in prison. Unfortunately for Bulger, that’s where he remains to this day, after being charged with 19 counts of murder among numerous other crimes. He is 87 years old.
19. ANTHONY ACCARDO
Known as ‘Big Tuna’, Accardo turned to crime in his early teens and quickly gained prominence working for one of the most notorious gangsters of all time, Al Capone, in his Chicago crime syndicate. His main role was performing hits for Capone, and he was allegedly an active participant in the Valentine’s Day Massacre in which seven men of Capone’s rival Irish-American gang were shot dead with sub-machine guns inside a garage in the Lincoln Park neighborhood of Chicago. Accardo was allegedly involved in other murders, including beating two men to death with a baseball bat. With all this under his belt, it might surprise you to know that the only crime Accardo was ever convicted of was tax evasion. He spent six years in prison in 1960. Accardo always denied any involvement with the mob, and died of natural causes in 1992.
18. AL CAPONE
Capone, also known as ‘Scarface’, was the boss of the Chicago Outfit. Capone knew how to make crime pay, making a fortune upwards of $100 million before being convicted for tax evasion in 1934. Growing up in the slums of Brooklyn, Capone turned to crime after connecting with gangster Johnny Torrio who became his mentor. Capone worked under him and eventually moved to Chicago to help run the brothel business. Over the years, Capone rose to being Torrio’s partner. Capone eventually inherited everything when Torrio retired, and he ran everything from gambling rackets to brothels. Every police probe into Capone’s dealings failed. At the time, it wasn’t uncommon for the police to stick mobsters with tax evasion just to get them behind bars. He was sentenced to 11 years in 1931. He died at home in 1947 from complications due to tertiary syphilis.
17. JOHN DILLINGER
Born in 1903, it didn’t take America’s most famous bank robber John Dillinger long to turn to crime. As a boy, he committed petty theft and by 1924, he had committed his first robbery of a grocery store. Even though he was jailed, he escaped and headed to Chicago where he organised one of the most infamous bank robbing circles in history. Due to the crime spree that ensued and Dillinger’s evasion of the authorities, he captured public interest and was prominent in the media. Unfortunately for him, it didn’t last long and he was shot and killed outside a movie theater during an FBI sting.
16. ENOCH JOHNSON
Fans of the HBO series Boardwalk Empire may be familiar with Enoch Johnson. ‘Nucky’ Johnson was a prominent figure in Atlantic City. Johnson wasn’t just a bootlegging mastermind of the prohibition era, but a strong political figure, making his rule largely undisputed. In the 1920’s, people flocked to Atlantic City to let loose from the harsh reinforcement of anti-alcohol laws. Johnson hosted lavish parties and lived a luxurious life, based on his profits from bootlegging, prostitution and gambling rings. Johnson gradually began to lose his power and his wealth when the prohibition was repealed in 1933. As we’ve seen numerous times already, he was imprisoned for 10 years in 1941 on tax evasion charges. He claimed bankruptcy in order to avoid paying the fines he had incurred, and lived out his days in a property owned by his wife’s family. He died at the ripe age of 85 in 1968.
15. BILLY THE KID
Billy the Kid was born in New York City in 1859. He was known as a thief and headed west where he ended up joining a gang of gunfighters called The Boys, to fight in the Lincoln County War. Billy switched sides and ended up fighting for the opposing side. After that was over, he continued to terrorize the west, stealing cattle and horses. He was arrested in 1880 for killing Sheriff Brady during the gun battles of the war. Despite being sentenced to death, Kid managed to escape, killing two guards. A man hunt ensued and he was killed by Sheriff Patrick Garrett on July 14, 1881. Billy the Kid was just 22 when he died, but his escapades in his short life were enough to make him a household name that remains remembered to this day.
14. PABLO ESCOBAR
Escobar, along with a few other criminals, created the Medellin Cartel and controlled a huge portion of cocaine shipped to the US from Colombia in the 1980’s. Despite being a crime lord, the public admired Escobar for his generous charity work. This quickly turned when his lust for power heightened. Escobar was elected as a member of Colombia’s alternative government, but by this point the cartel was bringing in hundreds of millions of dollars in profit weekly. The justice minister exposed him, and Escobar was forced to resign. The minister was later killed as a result. Escobar was implicated in the bombing of a jetliner that killed more than 100 people, which turned many of his own against him. He surrendered in 1991 and authorities allowed him to build his own luxury prison. Escobar still wasn’t happy and escaped. He was eventually tracked down and shot dead after a pursuit.
13. BONNIE AND CLYDE
Bonnie and Clyde were lovers and criminals who traveled the central US robbing people at their pleasing – and killing those who tried to stop them. The murderous couple committed numerous bank robberies with the help of their gang, from 1930-1934, as well as smaller robberies of gas stations and grocery stores. At the time, the newspapers sensationalized their story and they garnered public interest. Although Bonnie is often depicted as a gun wielding, cigar smoking murderess, another gang member testified that he had never seen her shoot a gun at police officers. The pair lived a life on the run, hiding where they could, and evaded arrest until they were ambushed and shot dead in Louisiana in 1934.
12. ELLSWORTH JOHNSON
Ellsworth ‘Bumpy’ Johnson, was the mob boss in New York City’s Harlem. Johnson was the main Harlem associate of the Genovese crime family in the 40’s and 50’s. He was able to strike a deal with the Genovese to enable bookmakers to stay independent, as long as they paid their tribute fees. This was hailed as a great victory and saw Johnson become well respected in the community – where many thought it impossible that a black man could strike such a deal at that time. Johnson was a popular celebrity figure in Harlem, with friends like Billie Holiday. He was arrested on drug conspiracy charges in the late 50’s and although he claimed it was a set-up, spent two years in Alcatraz. He was released and was under federal indictment for more narcotics charges when he died of congestive heart failure in 1962.
11. JESSE JAMES
With his brother Frank, Jesse James became an infamous train and bank robber. Contrary to what you may think, James and his brother came from a well-to-do family – their father was a Reverend. Their farm was savagely attacked by Union soldiers, inspiring the brothers to take the law into their own hands and turn to a life of crime. James is often seen as a ‘Robin Hood’ type figure, but there is no evidence to show they gave anything to the poor. They were well respected in their community as good family men. Unfortunately for them, they planned one last robbery with Charlie and Bob Ford, but the bounty on the James’ was so big, that the Ford’s decided to cash in. Bob Ford shot Jesse in back of the head in his own home. Frank surrendered months later but was acquitted and resumed a quiet life.
10. STEPHANIE ST. CLAIR
The formidable ‘Queen of Harlem’, Stephanie St. Clair, was born in the French Caribbean in 1896. She settled in Harlem and quickly set up an impressive organised crime empire. Known as ‘Queenie’, St. Clair was a glamorous, sophisticated and multi-lingual woman. Within a short period of time, she was running the extortion gang, Forty Thieves. She was the mastermind behind much of the Harlem numbers rackets, an illegal lottery that she ran with Ellsworth Johnson. Together, they both made a fortune – as well as a lot of enemies. A war ensued when rival Dutch Schultz tried to push St. Clair out of business and take over her operations. 40 people were killed and Schultz won. St. Clair went to prison for the murder of her husband, Sufi Abdul Hamid. After her release, she spent the rest of her life dedicated to the civil rights movement, and died in 1969.
9. GRISELDA BLANCO
She may have looked harmless, but ‘The Godmother’, Griselda Blanco is thought to have killed over 200 people during her run trafficking drugs from Colombia to the US. Blanco had a difficult childhood and turned to prostitution at an early age. It didn’t take long for her to become involved in the cocaine trade and the Medellin Cartel. Blanco helped push drugs through to America by creating undergarments that could conceal large quantities. Blanco moved to Miami, where she continued to run a huge narcotics ring. The authorities were aware of her, and fearing imprisonment, Blanco fled to Colombia. She evaded authorities for a decade before being arrested and sentenced to 15 years on drug conspiracy charges. She received a further 10 years for murder and was released in 2004. Blanco was gunned down and murdered in 2012, as she exited a butchers shop in her home town of Medellin.
8. GEORGE MORAN
Known better as ‘Bugs’, George Moran was Al Capone’s rival in prohibition-era Chicago. It was Moran’s men that Capone gunned down in the Valentine’s Day Massacre. Moran was notorious for being ruthless and brutal. Legend has it that he used to openly gun down rivals as well as civilians, believing he was untouchable. It’s also said that he kidnapped one of Capone’s bodyguards who he then castrated and brutally tortured before posting his remains back to Capone. Moran maintained his territory throughout the battles but eventually lost power and respect after the majority of his key members were killed in the massacre. He left the area and tried to continue to make money through lesser crimes. He was convicted in 1939 and not released until 1943. By then, he was penniless. He was sentenced to prison for robbery in 1946, where he died in 1957 of lung cancer.
7. BABY FACE NELSON
Lester Gillis, AKA ‘Baby Face Nelson’ was a bank robber and criminal active in the mid-20th century. He would go on to participate in robberies with John Dillinger and his gang. After Dillinger’s death, Nelson was named Public Enemy No.1. A man of only 5 feet 4, Nelson also had a short temper. His youthful appearance earned him his nickname, ‘Baby Face’. Nelson robbed a bank in Chicago in 1931, and was rewarded with a year in jail. He escaped while travelling to be tried on a separate robbery charge and it wasn’t long before he met Dillinger. Nelson continued to operate when the Dillinger gang dissolved, but was chased by the FBI, who ambushed him. Despite being hit 17 times, he managed to escape. He died the following day at the age of 25, on November 28th, 1934.
6. BENJAMIN SIEGEL
Benjamin ‘Bugsy’ Siegel was born in Brooklyn in 1906. He was raised in an area high in gang activity and began to extort money from pushcart peddlers on the Lower East Side. Siegel and another hooligan, Meyer Lansky, soon connected and set up the Bugs-Meyer gang. They were Jewish mobsters with a series of ruthless contract killers that they shamelessly branded Murder, Inc. After becoming involved with Charles Luciano and taking out hits, he moved to Las Vegas in 1940 where he built the Flamingo Hotel and Casino. Siegel’s dream of building a gambling mecca didn’t last. He mismanaged the building of the Flamingo by millions of dollars and Lansky was furious. In 1947 Siegel was killed at home by a fusillade of bullets through his living room windows. At the same time, Lansky’s men declared a takeover in the Flamingo.
5. FRANK LUCAS
Frank Lucas operated a heroin ring in Harlem during the late 60’s and early 70’s. He was so prominent in his neighborhood that it wasn’t uncommon for him to execute people in the street. Lucas boasted (to the disgust of many) that he used coffins of dead American servicemen to smuggle the drugs back to America. Lucas was a protégé of Bumpy Johnson. Prior to meeting Johnson, Lucas had been committing petty crimes like pool hustling. Notorious for stretching the truth, a lot of what Lucas claims to be true has been disputed. According to Lucas, he was making $1 million dollars a day selling drugs in New York. Eventually the authorities caught on and raided his house, where they found half a million in cash. He was sentenced to 70 years in prison, but provided information and his sentence was reduced to time served plus lifetime parole. Lucas and his family were placed into the witness protection program.
4. CARLO GAMBINO
Together with John Gotti and Paul Castellano, Gambino was one of the most prominent mob bosses of the 21st century. The Gambino crime family had almost 800 members – and is still active today. There was hardly anything off limits, from loan sharking to security fraud and construction. For a relatively uneducated man that never finished high school in Italy, Gambino created one of the most lucrative organised crime rings ever known. Gambino’s escapades over the course of his life are extensive. Many speculate that it was him who put the hit out on Joseph Colombo, head of the Colombo crime family. Although his crimes were plenty and severe, Gambino avoided prison. He was indicted for tax evasion in 1937 but his sentence was suspended. He died at home of natural causes in 1976.
3. MEYER LANSKY
Meyer Lansky came up through the ranks in a similar fashion to his one-time friend and partner, Bugsy Siegel. Russian born Lansky arrived in America in 1911, and had a tough upbringing. Despite this, Lansky developed into a bright young man with a great mathematical mind – and a cock sure attitude. He became involved with big time mobster Arnold Rothstein, who took it upon himself to mentor Lansky. Years later, he was one of the main kingpins that organised the national crime syndicate, using his financial acumen to work the system and make millions of dollars. Lansky attempted to retire in the early 70’s and move to Israel to avoid arrest. However, his residency was denied and on returning to the US, he was arrested. Most of his charges were dropped after a medical exam showed that he was seriously ill. He died of lung cancer in 1983.
2. HENRY HILL
Brooklyn born Henry Hill gained notoriety working his way up in the Lucchese crime family. Due to his Irish heritage, Hill could never be a ‘made’ man as he wasn’t fully Italian, but his attitude and charisma saw him become an integral part of the Lucchese family. Hill’s first stint in prison came after he beat up a gambler whose sister worked for the FBI. It cost him ten years. Using his prison contacts, Hill entered the drug trade. His operation grew larger until he succumbed to cocaine addiction. Becoming a liability, he was put on the hit list. When Hill realized that, he became an informant. Although he was put into witness protection, he was kicked out of the program when he blew his cover two years later. Hill became somewhat of a celebrity in his later years as the subject of books and films, including Goodfellas. He died in 2012, aged 69.
1. TERRY ADAMS
Terry Adams is the head of a British organised crime syndicate, known as the Adam’s family. Police dubbed the gang worse than the Kray’s – impressive. Although the extent of the crimes are unclear, the family have been linked to 25 murders and have an estimated value of £200 million, since their formation in the 1980’s. The London based gang are reportedly involved in drug trafficking, extortion and security fraud. Attempts have been made by police to downplay the family’s activities, but it’s thought that they are still active, even though Terry Adams was sent to prison in 2007 for money laundering. In February 2010, his nephew was convicted of disposing the bodies of four men, who he claimed had been killed at the request of his uncle. Adams served just half of his seven year sentence before being released in 2010.
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