Everyone loves a good heist movie. From the planning to the execution and finally, the victory, heist films completely undermine our moral expectations and enable us to root for the bad guy, guilt-free. While cinema has given us some of the best thieves in history, there are a whole lot more of them out there in real life and, throughout history, there have been a number of highly successful and incredibly underhanded thieves at work.
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While we wouldn’t want to meet these guys face to face; their abilities are undeniable. Collectively, the efforts of these swindlers have racked up one of the biggest debts in the world, taken from right under our noses. Keep a close eye on your wallet; these notorious thieves would pocket it in a second.
10. Doris Payne
As one of the most notorious living jewel thiefs in the world, Doris Payne is something of a cult figure; her six decades of criminal activity were immortalised in a 2013 documentary (in which she starred), including the story of her most notorious heist - a $500,000 10-carat diamond ring in Monte Carlo in the 1970s.
Often posing as a rich client and asking to see the assorted finery up close, Payne would then charm and distract the unnassuming store clerk and slip her item of choice into her bag. Eventually caught and imprisoned in 2011 at the grand old age of 80 (for stealing a 1 carat diamond ring, no less), the West Virginia has shown no signs of slowing up; she has been arrested several times since then and is also suspected of stealing a $33,000 diamond ring in North Carolina.
9. Derek "Bertie" Smalls
The 1960’s and 70s were something of a golden age for British armed robberies, and Derek "Bertie" Smalls was at the height of the game, committing himself to a life of crime at the age of 15. Smalls' pièce de résistance was his robbery of the Ilford Barclay's Bank branch in 1970, pocketing a mammoth £237,000 - a record at the time. Fleeing the scene, the east London native escaped to Paris and later to the Costa Del Sol, where he followed the hunt for his capture through newspapers.
Smalls eventually gave himself up to the Britsh police in 1974 and was given immunity in return for his help in securing convictions for his underworld acquaintances. He was the first true “supergrass” informant, dying of natural causes in 2008 despite the numerous revenge bounties - including the alleged £1m that the Kray twins (above) - placed on his head.
8. Carl Gugasian
An Ivy League-educated army officer with a PhD in statistics and probability, Carl Gugasian probably never intended to become a career criminal; after planning a series of mock robberies in his spare time, though, the Pennsylvania native - a convicted juvenile offender - began to develop a notorious reputation as the "Friday Night Bank Robber".
Known for his meticulous planning of heists (most of his robberies were small town banks near forests, allowing for a better escape route) and for wearing gruesome face masks when performing the heists, Gugasian was eventually tracked down and arrested in 2002. His willingness to co-operate with the subsequent investigation saw his sentence reduced from 115 years to 17; Gugasian, meanwhile, now teaches calculus to other inmates.
7. Frank Abagnale Jr.
Immortalised by Steven Spielberg and Leonardo Di Caprio in 2002's Catch Me If You Can, Frank Abagnale Jr is one of the most celebrated con men in the world. Having successfully impersonated an airline pilot, a doctor, a lawyer and a prison officer, Abagnale was eventually arrested in France in 1969, serving a short prison sentence there (as well as an additional six month sentence in Sweden) before being extradited to the US, where he was given a 12-year sentence.
Following his parole in 1974, he began a legitimate career as a security consultant, advising banks on anti-fraud measures, while he continues to work closely with the FBI and other security agencies through his Abagnale & Asssociates security firm. He also remained close friends with FBI agent Joseph Shea - the man originally tasked with capturing him - until Shea's death in 2005.
6. Albert Spaggiari
Described in obituaries as cavalier and stylish, Albert Spaggiari's life certainly reads like a Dumas novel; a former paratrooper with ties to far right nationalism (Spaggiari was alleged to have a portrait of Adolf Hitler on his wall), he spent time as an informant for the Chilean intelligence services before successfully trying his hand at armed robbery in 1976. Stealing an estimated 30m to 100m francs from the Société Générale bank in Nice, Spaggiari was subsequently dobbed in by an acquantaince before escaping from police custody a year later.
He lived out the remainder of his life on the run, probably in Argentina, before his death from throat cancer in 1989; the proceeds of the Nice robbery have never been found or recovered.
5. Jesse James
A legendary criminal of the American Civil War era, Jesse Woodson James was one of the first of his kind. After surviving several close shaves while fighting with a Confederate militia, he formed the James-Younger gang, carrying out robberies as far afield as Iowa and Texas; many of these robberies were performed in front of crowds, with a theatrical element to them, serving to cultivate a Robin Hood-like persona.
James was infamously shot and killed by another criminal acquaintance, Robert Ford, in 1882 (who himself was murdered in 1892 as an act of revenge); he has since been portrayed as a folk hero and a rebel, particularly in the American south.
4. Bill Mason
The quintessential gentleman jewel thief, Bill Mason made a living out of attending glamorous high society get-togethers, schmoozing with the assorted guests - and then robbing them blind. Estimated to have stolen around $35m worth of jewellery during his career (Robert Goulet, Armand Hammer and Phyllis Diller were among his victims), Mason documented his story in a 2004 memoir, Confessions of a Master Jewel Thief, where he also explains how he returned the Olympic gold medal he stole from Johnny Weissmuller (above) out of guilt.
In a 2004 interview with The New York Times, he expressed remorse for the emotional impact of his crimes - especially on his own family - although when asked if, given the chance, would he do it all again, he argued that he "wouldn't be able to promise" otherwise.
Another divisive figure, Munisamy Veerappan Mallar - known more commonly as just Veerappan - was an Indian bandit who spent nearly 30 years evading police capture, before his death at the hands of a Special Task Force in 2004.
Initially making his name as an effective poacher and smuggler of ivory and sandalwood, Veerappan quickly developed a more notorious reputation for his violent tendencies. He killed numerous police officers and anti-poachers, as well as local civilians he suspected of being police informants; during the late 1990s and early 2000s, Veerappan also kidnapped and ransomed several high-profile political and cultural figures. Although thousands attended his funeral, he remains a highly controversial figure in India.
2. Vincenzo Peruggia
The architect and perpetrator of what has been described as the greatest art theft of the 20th century, Vincenzo Peruggia's crime was almost laughable in its simplicity; in August 1911, he entered the Louvre museum in Paris disguised as a worker, removed the Mona Lisa from its frame and, concealing it under a robe, simply walked out of the front door with it.
Eventually caught when trying to fence the painting two years later, Peruggia's motive was the subject of some debate; some argue that he struck a deal with a forger, Yves Chaudron, to produce copies that could be sold, while others - including the court who sentenced him - believed that he wanted to return the painting to Italy for patriotic reasons. Either way, Peruggia spent just one year in prison, before serving in the Italian Army during the First World War; considered a hero in Italy, he died in 1925 of a heart attack at the age of 44.
Originally a lawyer by trade, Mithilesh Kumar Srivastava - better known as Natwarlal - was an Indian con man that developed over 50 aliases, creating a whole host of novel ways to cheat industrialists out of money. A talented forger, his signature trick was posing as a government official and selling the Taj Mahal to gullible foreigners (as well as other Indian landmarks such as the Red Fort, the Rashtrapati Bhawan and the Parliament House of India).
He escaped from jail numerous times during his distinguished career, including in 1996 when, aged 84 and wheelchair-bound, he somehow managed to evade his captors at a New Delhi railway station - the last time he was seen in public. The date of his death is uncertain (Natwarlal's lawyer claimed that he died in 2009, while his brother asserts that he was cremated in 1996), but his legend certainly lives on; anybody who pulls off a particularly smart con in India is referred to as a 'Netwarlal'.
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With ever-advancing technology and DNA detection practically available on tap, getting past the law is nearly impossible these days. Of course, a life of crime is hardly something that anyone wants to add to their list of skills, but by peering into the past, we can understand how things used to be when the criminals held more cards than the police.
This article was originally published in July 2015.