4 Most Notorious Gangsters of the Past

Gangsters — not the thugs that hang around with their pants to their knees or the ones that graffiti every remaining clear wall in their vicinity — but the classic gangsters, the ones involved in espionage, organized assassinations, and alcohol. Which ones are the most notorious?

Sam Giancana was expelled from school at the age of ten and sent to St. Charles Reformatory but this didn’t have the desired effect. He started out as the wheelman (or driver) for Al Capone, working his way to the top of Chicago’s illegal gambling operations. He joined the 42 gang in 1921 (who carried out low-level tasks for members of the Chicago Mafia of the 1920s, led by the notorious gangster Al Capone).

Giancana became the head of the Chicago Outfit (the city’s branch of the Mafia) in the 1950s, and by 1955 was controlling the gambling and prostitution operations, narcotics trafficking, and many more illegalities in his hometown. In the end, he was killed with a shot through his head and chin while cooking. Lovely.

Sam Giancana had many links to famous people — he was a friend of Frank Sinatra, had connections to the Kennedy’s, and reportedly, Marilyn Monroe spent her last living day with him. Read more on his life here.

An old fashioned gangster, an outlaw, Jesse James was the most famous member of the gang known as the James-Younger Gang. Jesse and his brother Frank were raised by a family of prestigious farmers. One day, their house was brutally attacked by Union soldiers. When Jesse was 16, he and his brother joined as Confederates riding alongside William Quantrill and “Bloody Bill” Anderson.

They’ve been accused of treating Unions cruelly due to the brutal treatment they received. Because of this, they rebelled and took the law into their own hands robbing trains, banks and stagecoaches that were owned or operated by a Northern institution. From 1860 to 1882, the James Gang was the most feared band of outlaws in American history — they were responsible for more than 20 bank and train robberies, stealing an estimated $200,000.

All attempts to catch them failed — they killed everyone that stood in their way. In the end, the government decided it needed a new plan. They made the reward for their capture gigantic, so gigantic that they hoped one of their own gang would turn traitor. It worked — Jesse James was very OCD, and as he turned his back to adjust a wonky picture frame, he was shot in the head by Bob Ford (a man working with them on their latest robbery). Read more on him here.

Women can be gangsters too! Griselda Blanco, known as the “Cocaine Godmother”, was raised by an abusive mother, turning to crime and prostitution at a young age. Not too long after, she became involved with Colombia’s infamous Medellin Cartel, smuggling cocaine to New York, Miami and Southern California.

In 1975, US authorities intercepted a massive shipment of 150 kilos of cocaine — the biggest cocaine case in history at that time. Blanco and more than 30 of her partners were charged. This investigation was nicknamed “Operation Banshee” and became very well known to officers all around the world. Griselda fled to Colombia, but it wasn’t long before she returned to Miami, continuing to run crimes such as driveby shootings and murders linked to drugs and money.

She always managed to escape the authority — until 1985 when she was captured in Irvine, California. She received 15 years prison sentence. After that, she was accused once more but pleaded guilty on all three murder charges, receiving a 10 year sentence after which she was freed in 2004. However, she was shot by two gunmen on motorcycles whilst walking out of a butcher’s shop. Read more on her here.

Alphonse Gabriel “Al” Capone, probably the most well-known gangster of all times, came from a respectable, professional family. The Capones lived in something a little more than a slum, but it wasn’t this that turned him to crime, but his schooling at a violent Catholic institution. He was a promising student, but was expelled at the age of 14 for hitting a female teacher.

Then, Capone met the gangster Johnny Torrio, who taught him to run a business while while maintaining a respectable front. He joined Torrio’s James Street Boys gang, eventually rising to the Five Point Gang. In one of his scrapes, he was slashed with a razor across his left cheek which earned him the nickname “Scarface”.

In 1925, Torrio died, and Al Capone became the crime king of Chicago, running gambling, prostitution and expanding his territories by gunning down rival gang members. One of his popular endeavors was during the 1920s when all pubs were shut down and all alcohol was banned. He convinced the authorities to sell non-alcholic beer, making gallons and gallons of barrels of this beer and delivering them to pubs. After the cops were gone, he’d come out with these syringes of ethanol (pure alcohol), and inject them into the barrels.

Capone was also responsible for the St. Valentine’s Day massacre, which made the city see who he really was, turning against him. In 1931, Eliot Ness (a friend of a victim of Capone’s) and The Untouchables captured him for tax evasion. He was sent to Alcatraz, in which he spent his last year in the hospital section being treated for syphilis. He was released in 1939 but slowly deteriorated in his Palm Island estate in Miami, finally dying in 1947 of cardiac arrest. Read more on him here.