People have always been obsessed with gangsters and mobsters. Despite the violent nature of their crimes and their seemingly blatant disregard for the law and for others who get in their away, there is something alluring about the power they wield and the legacies they leave behind.
10. Bonnie & Clyde (1910 – 1934 / 1909 – 1934)
Many gangsters are romanticised in the years following their deaths, but those who were active during the bank robbing heyday of the 1930s enjoyed surprising public support while they were still alive and committing crimes. Dubbed ‘Public Enemies’ by the FBI, many bank robbers during the era of the Great Depression were often favourably compared to Robin Hood. Of course, these bank robbers didn’t really go to the effort of actually sharing their money with Joe Public, but their crimes and actions seemed glamorous and even enviable to the downtrodden who were suffering financial hardship during this time. Few criminals managed to capture the imagination of the public like Bonnie Parker and Clyde Barrow. Considered to be the Romeo and Juliet of the criminal world, the pair formed a gang with other outlaws and went on a two-year crime spree stealing cars and robbing general stores, gas stations and banks. Although time and time again they managed to successfully evade capture by driving across state lines and laying low wherever possible, many of their crimes were small-time and some of their riskiest robberies only netted them a few dollars. The gang was whittled down following numerous run-ins and shootouts with the police, but the law finally caught up with Bonnie and Clyde in 1934 when their car was ambushed by a posse of lawmen in Louisiana. The posse of police officers took no chances and opened fire without any advanced warning, firing more than 150 rounds at the car and riddling the couple with bullets. Souvenir-hunters swarmed the vehicle and tried to collect any remnants they could before they were warded off by police, and thousands of people queued up for a chance to see their bodies when they were publicly displayed at a funeral parlour in the town of Arcadia.
9. John Dillinger (1903 – 1934)
Of course, it’s impossible to discuss the celebrity status of some bank robbers during the 1930s without mentioning John Dillinger. Dillinger was the head of The Terror Gang, a band of outlaws (most of whom met each other in prison) which included notable gangsters like Baby-Face George Nelson, Pretty Boy Flloyd and Machine Gun Kelly. In the space of just one year, Dillinger’s crime wave swept across Indiana, Wisconsin, Ohio and South Dakota as he and his gang netted tens of thousands of dollars by robbing more than two dozen banks. The gang even targeted police stations when they needed to stock up on guns, ammunition and bullet proof vests. Dillinger managed to successfully escape from prison twice during his criminal career (one time by whittling a pistol out of a block of wood), but he was finally stopped when the newly launched FBI tracked him down in Chicago in 1934 and shot him to death outside of a movie theatre on July 22.
8. Frank Lucas (1930 – )
Many gangsters have relied on the drugs trade to build their crime empire, but few revolutionised this illegal revenue stream like Frank Lucas did. Operating out of Harlem during the late 1960s and early 70s, Lucas went directly to the source for his illegal drug shipments. Lucas personally travelled to the Golden Triangle area in Thailand (one of the biggest opium-producing places in the world) to establish connections which could help him compete against the stranglehold the Italian mob had on the drugs trade in the United States. Although it has been disputed as to whether or not Lucas smuggled heroin using the coffins of dead American soldiers, most of the shipments were concealed in pieces of furniture and then flown over to the United States. Lucas sent relatives and close friends he could trust to Bangkok to oversee the operation and by cutting out the middleman he made a huge profit margin on his illegal activities. Lucas amassed a personal fortune and invested in property and clubs, but he was raided by the DEA in 1975 and sentenced to 70 years in prison. Lucas cooperated with authorities and provided evidence for more than 100 convictions and he was released in 1981.
7. Benjamin ‘Bugsy’ Siegel (1906 – 1947)
Some of history’s most famous mobsters couldn’t be further from the image of the care-free, impulsive bank robbers of the Great Depression. Organised crime in North America rose dramatically during the 1920s thanks in large part to Prohibition. Bugsy Siegel was a member of one of the many bootlegging gangs during this period which benefited from the illegal booze business. Bugsy had a fearless, brutal reputation and he became a hitman for rising crime boss Lucky Luciano, and it is thought that he was one of the trigger men involved in the killings of rival mob bosses Joe Masseria and Salvatore Maranzano. However, it wasn’t long before Bugsy earned a bounty on his own head so he was sent to California to develop gambling syndicates. Bugsy quickly found his niche and the money started pouring in from this new revenue stream. He took over the numbers racket in Los Angeles and, as his power and reputation grew, he befriended big name Hollywood stars as well as influential politicians and lobbyists. After being acquitted of a murder charge in 1944, Bugsy headed to Las Vegas in the hopes of becoming a legitimate businessman. He turned his attention to the Flamingo Hotel and went on wild spending sprees to make it the ‘place to be’ in Vegas, but he was murdered in 1947. No one was charged with Bugsy’s murder but it is widely believed that his associates had grown tired of waiting for the profits to show from his reckless spending habits and they sought a permanent solution to the problem.
6. Ronnie and Reggie Kray (1933 – 1995, 1933 – 2000)
Ronnie and Reggie Kray were the violent kings of the London West End during the 1960s. Starting with protection rackets in the 1950s, the Krays portfolio of crime went on to involve hijacking, robbery, arson and murder. The brothers used their criminal activities and influential connections to acquire a string of nightclubs and other properties in London, and the two enjoyed a celebrity status throughout the 1960s as they brushed shoulders with big-name stars like Judy Garland and Frank Sinatra. The Krays violent reputation stopped victims and witnesses from giving evidence against them. However, their reign of intimidation ended in 1968 when the brothers (along with 15 of their affiliates) were arrested by Scotland Yard. The police had been collecting evidence on the brothers for years and the pair were convicted of murder and sentenced to life imprisonment.
5. Amado Carrillo Fuentes (1956 – 1997)
His name may not be as well-known as some of the other gangsters on this list, but Amado Carrillo Fuentes was a hugely successful drug lord who revolutionised the drug trade out of Mexico. Nicknamed “The Lord of the Skies”, Fuentes controlled his drug empire by using private aircraft to transport and distribute huge quantities of cocaine around the world. Fuentes benefitted from the crackdown on Colombian cartels during the late 1980s and it is estimated he was worth an estimated 25 billion dollars. Fuentes owned more than two dozen Boeing 727s in his private fleet and he was regularly transporting tonnes of illegal drugs from Peru, Colombia and Bolivia. Under pressure and surveillance from the DEA, Fuentes unsuccessfully sought asylum in Russia and Cuba during the 90s. In July 1997, he underwent extensive plastic surgery to change his appearance but he died during the operation.
4. Jesse James (1847 – 1882)
Outlaw bandits like Billy the Kid and John Wesley Hardin carved their names in the history books by cutting a violent path through the American Wild West, but other gangsters during this time had a more ‘thoughtful’ approach to crime. Although he was far away from the ‘businessman’ criminals of the early 21st century, Jesse James became a folk legend during a time when outlaws were generally considered ruthless and violent thugs. A veteran of the American Civil War fighting for the Confederate army, some modern historians believe that it was political disillusionment which drove Jesse James to rob banks, trains and stagecoaches. Between 1866 and 1882, Jesse James allied himself with various gangs and pulled off some of the most audacious armed robberies in American history. In 1869, James struck up correspondence with the editor of the Kansas City Times and his writing portrayed an innocent man fighting for a political cause. These published letters helped him gain support and admiration from many members of the general public and others sympathetic to the Confederate cause. Whatever the motivation for his crimes was, James proved to be an elusive, notorious criminal who was on the wrong side of the law for almost 20 years. James’ death came at the hands of his friend and fellow gang mate Robert Ford who shot him in the back of his head. Although Ford was granted a full pardon and reward from the governor, he was reviled by the public for his cowardly betrayal.
3. Griselda Blanco (1943 – 2012)
photo: Paisadeoro / Wikicommons
While it’s pretty clear that the criminal underworld has always been dominated by men, Griselda Blanco could stand up against any of the most ruthless and fearless gangsters of the 20th century. Nicknamed the “Cocaine Queen”, Blanco was a petty juvenile delinquent in Colombia before she began working for the infamous Medellin Cartel by helping them export and smuggle cocaine. Emigrating to the United States in the 1970s, Blanco quickly stepped up her narcotics game and it wasn’t long before she was running her own drug empire in New York. She fled back to Colombia when the DEA started getting close to her operation, but she returned to the States and settled in Miami. Blanco’s drug ring expanded considerably as she took advantage of the cocaine scene during the late 1970s and 80s, and she was one of the most important figures in the Cocaine Cowboy Wars during this period. It is believed that she was behind at least 200 drug-related murders and at one point her operation was bringing in a staggering $80 million a month. However, Blanco’s ruthless penchant for murder brought her under increased investigation from the authorities and her competitors made several assassination attempts. She moved to California to escape the heat but she was finally arrested by the DEA in 1985. Blanco was given a sentence of up to 15 years for drug charges and even continued to run her drug operation from her prison cell, but she was called back to court in 1994 for three counts of murder. The case collapsed after a bizarre series of events which revealed that a secretary in the Florida State Attorney’s Office was romantically linked with a star witness in the trial, and Blanco served the rest of her term before being released and deported back to Colombia in 2004. She was killed by a drive-by shooting in 2012.
2. Pablo Escobar (1949 – 1993)
photo: thierry ehrmann / flickr
Pablo Escobar was the most ruthless drug lord in history. Escobar spent his youth as a petty criminal on the streets of Colombia, but it wasn’t long before he realised that real power came from the drug trade. In the early 70s, Escobar started smuggling cocaine between Colombia and Panama before exporting it to the United States. In 1975, he created a power vacuum when he allegedly ordered the murder of Medellin Cartel dealer Fabio Restrepo. Escobar used the opportunity to expand his operation and it wasn’t long before he assumed complete control over all crime in Medellin. Almost 80% of all cocaine entering the United States during the late 70s and early 80s came from Escobar’s operation and it was estimated he was shipping up to 80 tonnes of product a month. However, Escobar’s rise to power didn’t stop in the drug trade. In 1982 he became a member of Colombia’s Congress and he used bribery to keep law authorities and the government on his side. It is thought that his relentless reign of terror was responsible for hundreds, if not thousands, of deaths. With a personal wealth thought to be in the region of $25 billion, Escobar was one of the most powerful men in the world and he enjoyed a ridiculously glamorous lifestyle with his extravagant portfolio of assets which included multiple mansions, airstrips, a private army and even a private zoo. In 1991, the Colombian government couldn’t turn a blind eye to his crimes any longer and they reached an agreement with Escobar for him to serve a 5 year prison term in a facility he built himself. La Catedral Prison was a predictably luxurious private retreat for Escobar, but when it was revealed that Escobar was still carrying on his illegal activities the government arranged for him to be moved to a ‘proper’ prison. He went on the run in July 1992 and a manhunt was formed by the United States and a Colombian task force to find Escobar. He was tracked to a suburb in Medellín in December 1993 and he was killed by authorities in a firefight.
1. Al Capone (1899 – 1947)
Arguably the most legendary and infamous criminal who ever lived, Al Capone’s power and public image epitomised the modern image of the gangster. Like most criminals during the 1920s, Capone started in small-time gangs before becoming a bootlegger and smuggler. Working for the Five Points Gang in Chicago, Capone was known as a ruthless enforcer and he became acting boss when the head of Five Points, Johnny Torrio, was injured in an assassination attempt by the rival North Side gang. Capone continued to efficiently run the Chicago Outfit’s gambling, prostitution and liquor enterprises as he vied for complete control of the area. This power struggle culminated in the infamous St Valentine’s Day Massacre of 1929 when prominent members of the North Side gang were gunned down in a bloody attack which is thought to have been orchestrated by Capone. Capone was at the height of his power, but the bootlegging wars had drawn increased attention from the authorities. Despite attempts to clean up his image (he famously opened up soup kitchens in Chicago to help feed those affected by the Great Depression), a federal investigation relentlessly pursued Capone and Elliot Ness’ ‘Untouchables’ squad finally cornered Capone with tax evasion charges. He was convicted in 1931 and sentenced to 14 years, transferring to Alcatraz in 1934. Capone famously received preferential treatment in prison, but the end of Prohibition diminished his power and his health rapidly deteriorated behind bars. He was paroled in 1939 and died in his mansion home in Florida in 1947.