The Baddest Gangsters of All Time

Preston Waters

The word gangster is one of the most overprescribed titles in the English language. Hollywood glorifies them, amateurs aspire to be them, musicians and artists attempt to emulate them. The glorification of the classic gangster may be a thing of the past now, as the modern media tends to emphasize the actions of those like the  Kardashians rather than addressing any pressing issues. While we do not condone their violence, we do feel there is something to be learned from history.

These entrepreneurs gone awry may have chosen the wrong path, but they did leave an indelible impact on society. Here are some of the baddest gangsters of all time. Make sure you don’t fall victim to these same pit falls:

Enoch “Nucky” Johnson

“Nucky” Johnson, who ran Atlantic City for 30 years, did so mostly through fear and charm. He captivated local residents with his style, gained their loyalty through his generosity, and controlled them with his shrewdness. He gained his unique position through another man’s fall, when “The Commodore” Louis Kuehnle was convicted in 1911 on charges of voter fraud, giving Johnson the opportunity to “pick up his toga,” according to a 1939 news story.

The state indicted Johnson, who was county sheriff at the time, on election fraud charges with Kuehnle and others, but he escaped conviction. Johnson capitalized on his resulting freedom. He exploited the Prohibition era and the city’s ability to illegally give visitors what others could not. For Johnson, the times made the man, and the man made everything of the times.

His Mafia-esque exploits included dealings with such organized crime heavyweights as Charles “Lucky” Luciano and “Scarface” Al Capone. His political power, under the appropriate title of Atlantic County treasurer, extended to Trenton and enabled him to maintain close relationships with New Jersey governors and intimidate people in the state’s criminal justice system.

His power over government could be attributed to what amounted to a gift from government: Prohibition. Also known as the “Noble Experiment,” Prohibition laws went into effect in 1920 and remained until 1933. The period was the pinnacle for Johnson and Atlantic City, which became known as one location that could never go dry.

Griselda Blanco

Griselda is one of the few women to ever make it to the notorious top echelons of drug dealing society. Obviously, drug dealing seems to fall more in the menswear category, but the female Scarface didn’t mind taking the heat. Griselda Blanco is mostly notorious for the drug wars in Miami that took place during the late 70s and 80s. Save for a few others, she’s one of the few American drug lords who prospered during the 80s amidst fierce competition as cocaine supplanted marijuana as the drug of choice.

Griselda was apprehended after attempting to escape authorities in California by the Drug Enforcement Administration. She spent about 20 years in the big house, and was released in 2004. After her release, Griselda decided to one-up her male counterparts one last time, and disappeared.

Bugsy Siegel

Benjamin Siegel was born in Brooklyn in 1906 and soon associated himself with fellow Jew Meyer Lansky. After running contract killings for Murder, Inc., Siegel — who was nicknamed “Bugsy” because of his unpredictable nature — went in cahoots with Lucky Luciano and his newly organized Syndicate. But killing for Luciano earned him enemies, and in the late ’30s, he was forced to escape to Los Angeles, where he had lived glamorously with movie stars.

He then discovered the gambling laws of Nevada. “Borrowing” millions from the Syndicate, he established one of the first casino hotels in Las Vegas, the Flamingo. But the resort was losing money, and when it was discovered in 1947 that he had stolen money from his friends, he was killed.

Featured in: The best portrayals of Siegel are in Warren Beatty’s Bugsy (1991) and The Marrying Man (1991) with Armand Assante.

Carlo Gambino

Carlo Gambino came from a family that had been part of the Mafia for centuries in Italy. He started carrying out murders when he was a teenager and became a made guy in 1921 at the age of 19. With Mussolini gaining power, he immigrated to America, where his cousin Paul Castellano lived. He became a thug for different New York families until he joined Lucky Luciano’s crew.

After Luciano was extradited in the ’40s, Albert Anastasia took over. But Gambino thought it was his time to shine and had Anastasia killed in 1957. He appointed himself Boss of the family and reigned with an iron fist over New York until his natural death in 1976.

Featured in: Al Ruscio played him beautifully in the TNT movie Boss of Bosses (2001). Other “Gambino” appearances include the made-for-TV movies Between Love & Honor (1995), Gotti (1996) and Bonanno: A Godfather’s Story (1999).

Pablo Escobar

Pablo Emilio Escobar Gaviria was a Colombian drug lord and leader of one of the most powerful criminal organizations ever assembled. During the height of his power in the 1980’s, he controlled a vast empire of drugs and murder that covered the globe. He made billions of dollars, ordered the murder of hundreds if not thousands of people, and ruled over a personal empire of mansions, airplanes, a private zoo and even his own army of soldiers and hardened criminals.
By the mid- 1980’s, Pablo Escobar was one of the most powerful men in the world. Forbes magazine listed him as the seventh-richest man in the world. His empire included an army of soldiers and criminals, a private zoo, mansions and apartments all over Colombia, private airstrips and planes for drug transport and personal wealth reported to be in the neighborhood of $24 billion. He could order the murder of anyone, anywhere, any time.

John Dillinger

After being released from the US Navy, in September 1924 he robbed a local grocer of $555. He was arrested and convicted and sent to Michigan City State Prison.

Released in May, 1933, Dillinger was released on parole and with two other ex-convicts, John Hamilton and Harry Pierpont, they began robbing banks in Indiana and Ohio. On 23rd October, the Dillinger gang robbed the Central National Bank of $75,000. The following month the gang got $27,000 from the American Bank in Racine. In early January 1934, they robbed another bank in East Chicago, Indiana, and during a gun-fight, killed a police officer.

Dillinger and his gang were arrested in Tucson, Arizona, and imprisoned in Chicago. However, while waiting to be tried for murder at Crown Point Prison, on 3rd March, 1934, Dillinger escaped from prison. With a new gang, including Baby Face Nelson, Dillinger robbed banks in Minnesota and Wisconsin.

The Chicago police persuaded Anna Sage, a local prostitute, to befriend Dillinger and lead him into a trap. On 22nd July, 1934, Sage, known as the “Lady in Red”, went to the Biograph Theatre. As Dillinger left the theatre, a team of police officers were waiting for him. One of them called out “John” and as he turned round the officers opened fire and Dillinger was killed in a hail of bullets.

Lucky Luciano

Charles “Lucky” Luciano was one of the most famous gangsters in the U.S. during most of the 20th century, credited with turning syndicated crime into a nation-wide organization based on legitimate business models. Born in Sicily, he and his family moved to New York City in 1906. At an early age he established himself as a creative thug on the Lower East Side and eventually worked his way up to being a top aide to crime boss Giuseppe “Joe the Boss” Masseria.

In the 1920s Masseria was involved in a prolonged turf war with rival crime boss Salvatore Maranzano. Luciano, who by this time had earned the nickname “Lucky” (supposedly by surviving a brutal attack on his life), made a deal with Maranzano and arranged for Joe the Boss to be assassinated in 1931. Luciano then arranged for the murder of Maranzano and became the biggest boss in New York City. With the help of childhood friend Meyer Lansky and strongman Benjamin “Bugsy” Siegel, Luciano then restructured organized crime. Together they created an organization that had a board of directors that focused on profits instead of traditional ethnic loyalties.

Luciano became a celebrity, living in high style and having celebrity pals such as actor George Raft and singer Frank Sinatra. His gangster fame caught up with him in 1936, when special prosecutor (and later New York’s governor) Thomas E. Dewey charged Luciano with 62 counts of compulsory prostitution. Luciano was convicted and sentenced to a minimum of 30 years in prison. In February of 1946 Governor Dewey struck a deal that released Luciano from prison and deported him to Italy (the legend is that during World War II Luciano used his contacts to help the U.S. government fight the Nazis).

Luciano, who had never lost his position as crime boss, even in prison, popped up in Cuba in 1947 and was again deported to Italy by U.S. officials. As he aged, his influence in the world of organized crime waned, but his celebrity status as one of the most flamboyant and creative criminals in modern history remained. He died of a heart attack in 1962.

Al Capone

If there ever was a gangster who earned the No. 1 spot, it is Al Capone. Alphonse Capone was born in 1899 to Italian immigrants in Brooklyn, New York, where he got his start in street gangs. He then joined the Five Points gang and became a bouncer. It was during these days that a series of facial wounds earned him the “Scarface” nickname. Capone moved to Chicago in 1919 and quickly moved up the Mafia hierarchy while working for Johnny Torrio (Capone became Torrio’s protege).

It was the time of the Prohibition, and Capone ran prostitution, gambling and bootlegging rings. In 1925, at the age of 26, Capone took over after Torrio was wounded in a gang war. Known for his intelligence, flamboyance and love of public attention, Capone was also known to be very violent; his role in the orchestration of the St. Valentine’s Day Massacre in 1929, in which key rival gangsters were murdered, proves this. In 1931, Federal Treasury agent Eliot Ness arrested him for tax evasion.

Featured in: Many movies have been made about Capone, but the most famous are probably The St. Valentine’s Day Massacre (1967) with Jason Robards, Capone (1975) with Ben Gazzara and The Untouchables (1987) with Robert De Niro.


Preston Waters

Preston Waters


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