When it comes to the amount of sheer planning, creativity, and outright lunacy that goes into them, few crimes rival the high profile, multi-million dollar heist. And when you consider the colorful characters and criminal masterminds behind these robberies, it’s easy why these crimes continue to be the subject of constant speculation and fascination. Whether the work of teams of highly trained thieves, lowly bank managers, or even a powerful dictator, here are ten of the biggest and most bizarre heists and burglaries in history.

10. The Great Train Robbery

One of the most famed heists in popular culture, The Great Train Robbery was one of the biggest robberies of all time when it was committed in 1963. The heist took place in Buckinghamshire, England, when a mail train transporting millions of pounds was boarded by a team of 15 robbers. The thieves used a fake signal light to stop the train, and after subduing the workers inside the first two carriages, loaded 120 mail bags containing 2.6 million pounds into some cars they had hidden near the tracks. The men all escaped the scene, but 13 of them were quickly captured following an extensive investigation by Scotland Yard. Two of the these men, Ronnie Biggs and Charlie Wilson, would later escape from prison and flee the country. Wilson was caught four years later in Canada, but Biggs famously eluded capture by hiding out in Brazil, and he was only apprehended when he turned himself in to authorities in 2001.

9. The Agricultural Bank of China Robbery

2007’s Agricultural Bank of China Robbery resulted in the theft of 51 million yuan (roughly $7 million U.S.), and it is said to be the biggest robbery in China’s history. The scheme started when the bank’s manager, Ren Xiaofeng, stole 200,000 yuan from the vault. His unlikely plan was to use the money to buy massive amounts of lottery tickets in the hope of winning a cash prize and returning the money before it was reported missing. Amazingly, the plan worked, and Ren made a huge profit off of his gamble even after returning the 200K. After enlisting the help of another manager, Ma Xiangjing, Ren proceeded to steal nearly 33 million yuan a year or so later, and a month after that another 18 million. In both cases, the men spent nearly all the money on lottery tickets, but they were only able to recoup 98,000 yuan, and the missing money was quickly noticed and reported. Ren and Ma were eventually captured, but very little of the stolen money was ever recovered, thanks to the astronomical amounts the duo had spent on lotto tickets.

8. The Great Brinks Robbery

When it was committed in 1950, the $2.7 million Brinks Robbery in Boston, Mass. was the biggest heist in American history. Dubbed “the crime of the century,” the heist was the work of an 11-man gang who used copied keys to gain entry into the Brinks Building. Once inside, they made their way to a room where employees were counting money, and after subduing the armed guards, collected $1.2 million in cash, along with another $1.5 million in checks and securities. The gang’s plan had been to sit on the money for six years, at which point the statute of limitations for armed robbery would have run out, but a police investigation quickly started turning up suspects. After a few of the men were arrested, the criminals started turning on one another, even going so far as to hire hit men and attempt drive-by shootings on suspected snitches. Eventually, though, all eleven of the original robbers were found out and arrested, and many received life sentences in prison.

7. The Gardner Museum Art Heist

In the biggest art heist in history, two men dressed as police officers managed to con their way into the Isabella Stewart Gardener Museum in Boston late one night in 1990. Once inside, the men overpowered the few guards on duty, tied them up, and left them in the basement. They then proceeded to steal several pieces of artwork by Rembrandt, Degas, Manet, and Vermeer, along with a few sculptures and historical artifacts. The total haul is now valued at $500 million, but both the thieves and the artwork have yet to be found. A number of possible suspects have been considered, from Boston crime boss James “Whitey” Bulger to the IRA, but no arrests have been made in connection to the case. Enough time has passed that the statute of limitations on the actual heist has passed, leaving the Gardner Museum art heist as one of the most successful and mysterious robberies of all time.

6. The Central Bank Of Iraq Heist

For sheer amount of currency stolen, no robbery compares to the Central Bank Of Iraq heist, which is said to have been perpetrated by none other than Saddam Hussein. The robbery happened just before the U.S. bombing of Iraq in 2003. In the middle of the night, a small group of men led by Hussein’s son, Qusay, went to the Central Bank with tractor-trailers and forcibly withdrew just under 1 billion dollars cash. Nearly $650 million of this was eventually found stashed in the walls of Hussein’s palace by U.S. soldiers. A handwritten note was later discovered linking Saddam and his son to the heist, but just who the other men involved were or what became of the remaining $350 million remains a mystery.

5. The Baker Street Burglary

The Baker Street burglary took place in London in 1971, when a team of well-equipped thieves tunneled into the Baker Street Bank and stole 3 million pounds worth of cash and valuables from safety deposit boxes. The criminals used a combination of metal cutting tools and explosives to tunnel to the vault from a nearby shop, and even had a lookout positioned on a nearby rooftop. Near the end of the heist, a ham radio operator overheard some of the lookout’s radio transmissions and contacted the police, who frantically searched over seven hundred banks within the area in hopes of honing in on the location of the transmission. They were unable to catch the robbers at the time, but nearly two years later a number of men were charged in connection with the robbery, though police believe the true mastermind behind the crime was never captured.

4. The Harry Winston Heist

One of the most downright brazen robberies in recent memory, the Harry Winston Heist went down in 2008 when a group of four men stormed into one of Paris’s most exclusive jewelry stores and made off with $108 million in diamonds. The men were disguised as women and armed with a .357 Magnum and a hand grenade. They quickly herded the employees and customers into a corner and started breaking open display cases, and after filling a suitcase with precious stones, made their escape. No one from this robbery has been arrested, but police suspect that the robbers– whom they’ve nicknamed “The Pink Panthers”– are a part of a larger criminal organization of Yugoslavians that may have been responsible for a number of other high profile jewelry heists. In the meantime, a $1 million dollar reward is still up for grabs for any information leading to the arrest of the thieves.

3. The Knightsbridge Security Deposit Robbery

One of the boldest and most successful robberies of all time, the Knightsbridge Security Deposit heist happened in London in 1987, when career criminal Valerio Viccei and a small group of accomplices armed with guns managed to make off with 60 million pounds in valuables and cash from safe deposit boxes. The thieves got into the vault by pretending to rent a safe deposit box of their own, and once inside they managed to overpower the employees and security guards and start breaking into the boxes. They escaped without incident, but a bit of blood left behind at the scene allowed police to trace the robbery back to Viccei, who was wanted for a huge amount of robberies in his native Italy. Viccei’s accomplices were quickly arrested, but he fled the country and for some time eluded capture. A known playboy and high roller, he was only arrested after he returned to England in an attempt to retrieve his prized Ferrari sports car.

2. The Banco Central Burglary

Considered to be among the biggest bank heists of all time, the Banco Central burglary took place in 2005 in Fortaleza, Brazil. The robbery was the result of painstaking planning by a small gang of burglars who tunneled over 250 feet to the bank’s vault from a nearby property. The robbers used a landscaping business as a front for their operation, an ingenious cover that allowed them to move massive amounts of dirt and rock out of the tunnel without looking suspicious. The tunnel itself was expertly constructed, and was said to have sophisticated lighting and even an air conditioning system. After three months of digging, the thieves finally broke into the vault and made off with over 165 million in Brazilian reals, or $70 million dollars U.S. Since then, police have made a number of arrests in connection with the burglary, and recovered roughly $9 million dollars of the haul, but the majority of the suspects are still at large.

1. The Antwerp Diamond Heist

Antwerp, Belgium is one of the diamond capitals of the world, with 80 percent of the world’s diamonds passing through the city before being sold on the market. A number of heists have taken place there, most recently a still-unsolved $28 million robbery in 2007, but the biggest of them all took place in 2003, when a team of master criminals known as the School of Turin managed to walk away with $100 million in uncut diamonds from the Antwerp Diamond Center vault. For sheer scope, ingenuity, and risk, few robberies will ever measure up to this one. The criminals had been planning the heist for years, and using copied keys and faked security camera footage, they managed to bypass the vault’s multi-million dollar security system, which had been thought to be impenetrable. The thieves escaped without incident, but DNA left at the scene allowed them to be tracked to Italy, where most of the gang has since been captured. The $100 million in diamonds, meanwhile, seems to have disappeared for good.

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