The 10 Greatest Heists in History

We have a strange history of idolizing criminal masterminds. Even thieves who don’t necessarily share their robbed riches with the poor still seem to retain the adoration of fans who live vicariously through their daring escapades. 

As technology and security evolve, so does the criminal guile that seeks to fleece hidden treasures — it's the darker half of innovation, creating a balanced Ying-Yang of wealth. American industries flourished with the advent of train transportation, until they had to contend with the ferocious Jesse James gang. Large banks responsible for the 1920s Depression fell victim to John Dillinger's string of robberies and drew little sympathy from people who held them accountable for the economic collapse. It’s unlikely we’ll see someone give Goldman Sachs their just desserts, but just this February a crew in Brussels proved massive diamond heists are still very much in fashion.

History has taught us that no matter how big the trap, there’s always a sneaky mouse willing to steal the cheese. Here are some of history's greatest heists.

1. Millennium Dome Raid

The year was 2000, and London had finally finished construction on the catastrophic waste of money known as the Millennium Dome. Among its many displays, was a world class Diamond exhibit. The crown jewel was the "Millennium Star" — a flawless 203 carat gem worth $250 million. The robbers planned an explosive smash and grab job, running in guns blazing and escaping on a waiting speedboat. Their plan was foiled, however, as London’s metropolitan police had coincidentally already had them under surveillance for a few armored car robberies, arresting them on site.

2. Isabella Stewart Gardner Museum Heist

In 1990, while the entire city of Boston celebrated St. Patrick’s day by chugging beer and smack-talking the Yankees — two thieves dressed as Boston police officers entered the museum and stole 13 works of art. The missing pieces include a Rembrandt, Manet, and a few by Degas, estimated at $500 million total. Empty frames currently hang in the room, in homage to the missing art and in hopes that they will one day be returned. This is one of the greater unsolved mysteries in American crime.

3. The Collar Bomb Bank Robbery

This one may sound familiar to anyone who’s seen 30 Minutes or Less, but the real story is far more tragic. In 2003, a middle-aged pizza deliveryman walked into a bank, handed the teller a note asking for the money in the vault — and then lifted his shirt to display a collar bomb around his neck and chest. After stealing the money, he got about 15 minutes away before state troopers arrested him.

He started screaming that he had been forced to perform the robbery and the bomb was going to go off. The police surrounded the area and waited for the disposal squad to arrive — but before they could get there, the bomb started beeping and blew up. The tale only gets stranger from there, with FBI investigators, a long paper trail of clues, and dead bodies hidden in freezers. Worth a read if you enjoy truth that’s stranger than fiction.

4. $6 Billion in U.S. Tax Stolen in Iraq

In all the chaos of post-Saddam Iraq — with private security contractors, former Iraqi military and the US army all fighting for control of the region — someone made off with over $6 billion dollars worth of the money Congress dumped on the country. Special inspector general for Iraq reconstruction, Stuart Bowen, admitted he couldn’t account for the money, and called it the "largest theft of funds in national history." The absurd quantity, complete lack of investigatory results, as well as the manner in which everyone just seemed to forget about it, makes this the largest and strangest of robberies.

5. The French Bank Vault Tunnelers

In 2010, a team of robbers used sophisticated and unknown tools to borrow underground and into a Parisian bank’s vaults — where they proceeded to rob over 100 safety deposit boxes. The value of the stolen items cannot be known, as wealthy clients confidentially managed their containers. A very similar crime occurred months earlier at a bank to the North of the city, with over 100 boxes robbed — making the same mystery team the top suspects.

6. Great Train Robbery

In 1963, £2.3 million (£40 million today) was stolen off of a post office train in England. The 15 member gang managed to pull off the caper without using a single gun. The money they stole was on it’s way to being burned, and the crew would have gotten away with it — had they not played a game of monopoly in a barn with all the stolen cash, and left fingerprints all over the place…seriously.

7. D. B. Cooper

A favorite among conspiracy theorists, D.B. Cooper performed the only unsolved air piracy act in American history.  In 1971, the unidentified man - known by his common epithet - hijacked a Boeing 727, extorted $200,000 and then leaped out of the plane with the money somewhere between Portland and Seattle. Despite years of searches, and an ongoing FBI investigation, neither the body or money have ever been recovered. The assumption is that D. B. parachuted to an uncertain fate, but his case remains active at the Bureau for over 40 years, and has amassed 60 volumes of theories.

8. Vastberga Helicopter Robbery

In 2009, an otherwise docile police force in Sweden had to face a highly organized gang of daring criminals, in the country’s first ever “Helicopter robbery.” The crew of thieves used a stolen helicopter to land on the roof of a cash depot building. They broke through glass with sledgehammers, blew through security doors with explosives and raided the cash store vaults — stealing bags of money as they made their escape. Police cars arriving on the scene had their tires blown out by caltrops that the criminals had littered all over the road. None of the thieves who were caught received more than 7 years in prison though, so if you’re going to practice your criminal skills in any country — Sweden might be a safe bet. 

9. Thomas Blood and the Crown Jewels Of England

The year was 1671, Thomas Blood was an Irish Assassin (obviously) who decided to try his hand at robbery. His humble target? The crown jewels of England, which are held in the Tower of London and surrounded by guards … a lot of guards! Blood’s plan involved costumes, a fake title, a fake wife (played by a prostitute) and a fake nephew which he claimed would marry the daughter of Talbot Edwards — the Keeper of the Jewels.

After securing a private viewing, the gang knocked Talbot out, smashed the Jewels with mallets and stuffed them in their pants to make a run for it. They didn’t get too far though, with several guards reportedly tackling them off their horses. Blood lucked out, however, as King Charles II was so amused by the attempt, he pardoned Thomas and let him retire on a nice spot of land in Ireland.

10. Antwerp Diamond Heist

This 2003 robbery was dubbed the “Heist of the Century” — with large quantities of gold, diamonds and jewelry getting lifted from the Antwerp diamond center. The estimated worth of the missing items was than $100 million, but as it turns out there was more to the story. Leonardo Notarbartolo orchestrated the robbery, and lived beside the diamond center for three years prior to the crime. As part of his sophisticated ruse, Leonardo posed as an Italian diamond merchant in order to gain credibility at the center.

More than 123 out of 160 safe-deposit boxes were forced open, each of which was made of steel and had a unique key/combination lock. Leonardo was arrested, though his entire crew got away. Years later, he gave an interview to Wired magazine, in which he claims the whole thing was an insurance fraud attempt by a diamond merchant who hired him. Apparently, the actual score was closer to $20 million — leaving the lion’s share of the theft to be suffered by the insurance company.