10 of History’s Most Brazen Thieves

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There’s an old adage that says “crime doesn’t pay.” Unfortunately, a lot of criminals steal things to make money precisely to ensure that crime does pay them. Now for some criminals this doesn’t pan out at all. But for others, it actually works out much better than you’d think. Sometimes the difference between crime failing and crime paying is just how brazen the thief involved is.

10. Stephane Breitwiser

If the media starts calling you the world’s greatest art thief, then it seems likely you met the bar for being brazen when it comes to your crimes. Stephane Breitwieser is the sort of thief that, if he was a character in a movie, you’d dismiss him as being unrealistic. That’s because this is a man who robbed over 200 museums and managed to pull in a collection of art worth  $1.4 billion.

Breitweiser is almost too suave to be believed. He would rob museums in broad daylight with guards in the room while he did it. He had a whole system down for how to get away with his crimes in a way that no one would suspect or even notice.

The Breitweiser method was to arrive at lunchtime. The museum would have fewer guests and the security staff would be rotating because many of them would be going to eat. He dressed like an affluent guy and carried a Swiss army knife with him.

He would case the museum to look for whether or not cameras are real or to see how the guards were patrolling. He’d use audio cues to let him know if someone was coming like a creak in the floor, or an accomplice who could cough to alert him to someone coming. 

His method of stealing paintings was bafflingly simple. When no one was looking, he would simply work the frame off of the artwork. Or he would cut it out of its frame, roll it up, and stash it in his jacket and then walk out of the museum like any other patron.

The most valuable painting he stole was worth nearly $5 million, Sybille of Cleves by Lucas Cranach the Younger.  He would steal small statues and other artworks as well by simply slipping them down his pants.

Part of the trouble with catching Breitweiser was the fact that he wasn’t trying to sell any of the paintings afterward. He was just an avid art lover and wanted to have an amazing collection. He was only caught when he returned to a museum shortly after robbing it and was recognized by a guard who had seen him previously. 

9. John Dilinger

John Dillinger is one of the most famous criminals in American history. In the early 1930s he became something of a legend for his string of high-profile bank robberies. It’s what led him to be a name that is still recognized by people today. And although the number of crimes he committed has been surpassed, he still holds that legendary status of a kind of outlaw like Billy the Kid or Al Capone.

Dillinger’s first attempt at a robbery came in 1924, when he tried to hold up a grocer. He was caught and sent to prison. While incarcerated, he actually perfected the craft of robbing banks thanks to the influence of fellow inmates who had more experience than he did. When he was paroled in 1933, he went out and robbed five banks in four months.

Dillinger was actually caught after this, but some friends from prison helped him escape. After that he and his gang went on a robbery tour of America, making their way from Indiana down to Florida and then Arizona. After being caught and sent to jail again, he once again proved his mettle by breaking a house. This is one of the most famous prison breaks in history and involved Dillinger carving a fake pistol out of wood and using shoe polish to make it look like metal.

Once again, Dillinger was on the run with a new gang. He managed to rob a total of 24 banks  before the FBI finally caught up with him. A sting operation was set up, and Dillinger was shot after leaving a movie theater.

8. Doris Payne

Doris Payne may look like a nice old grandma, and that’s kind of the point. When you set out to become an international jewel thief of some repute, you need to use all the tricks you have up your sleeve to get away with your crimes. Her pain, it was looking like she absolutely was not an international jewel thief of some repute.

Payne was born in Slab Fork, West Virginia, in 1930.  For the past six decades she’s gone out of her way to steal just about any piece of jewellery she could find that wasn’t nailed down. That includes a diamond ring in Monte Carlo that was worth $500,000, a $22,000 diamond ring in California, a $33,000 ring in North Carolina, and even $86.22 worth of merchandise from  a Walmart in Atlanta. No crime was too big or too small to get her attention.

It’s believed she’s used at least 22 aliases over her long career. She’s been arrested over 20 times in countries such as Greece, Britain, Switzerland, France and, of course, the United States. More than once she’s claimed that she was too ill for trial, and her age and frailty has led to judges going easy on her, letting her serve out sentences at home with ankle monitors… which she has actually committed crimes while wearing.

7. Carl Gugasian

While John Dillinger had carved quite a niche for himself as a bank robber, the man was no Carl Gugasian.  Gugasian committed his first robbery at age 15 and got shot for his effort. He seemed to go on the straight and narrow after that by heading to University and getting a degree, joining the Army, and even becoming part of Special Forces. Afterwards he returned to school, got a master’s degree, and even did a bit of doctoral work. Sounds like an upstanding citizen.

Despite all the efforts he put into bettering himself, it seems as though he put just as much effort into plotting bank robberies. He was a detail-oriented guy and planned them out nearly perfectly. A bit of research on his part led him to the conclusion that the best time to rob a bank was on a Friday night just before the bank closed. That’s what earned him the nickname of the Friday Night Bank Robber.

Because he was a smart guy, Gugasian and did a ton of research before he committed any crimes.He studied the area around every bank for days at a time before acting on everything. He needed to have a nearby wooded area that he could escape into, and a road that led into a freeway on the other side of the wooded area. He’d find out exactly how many employees were going to be in the bank at the time he was going to be there, and even what their day to day habits were. That included whether or not they drove themselves to work or if somebody came to pick them up.

 After all the prep work, the plan was pretty simple. Two minutes before the bank closed he would enter wearing a disguise. He would be covered head-to-toe n baggy clothes so you couldn’t even tell what race he was, or his weight. He would even crouch-walk into banks so that no one could hazard a guess as to what his actual height was.

He never had a getaway car waiting, instead he would run into the forest that he knew was nearby. He’d hide the money in a pre-selected place and then get on a bike that he’d left as his getaway vehicle. From there he would head to a van that he’d stashed a good distance away. This method allowed him to rob nearly 50 banks.

He was only caught when some teenagers stumbled upon a stash of survival gear and paraphernalia that he left hidden in the woods. Law enforcement was able to piece together who he was based on all the clues they found.


6. Bill Mason

The term cat burglar doesn’t get used much these days, and even when it does, you probably think of Catwoman more than anything else. But Bill Mason was the definition of a cat burglar. He used to steal valuables from celebrities including Robert Goulet, Phyllis Diller, and Armand Hammer, great-grandfather of Armie Hammer.

According to Mason, he made off with  $35 million worth of loot in his life.  And he managed to stay out of jail except for a three-year stint. What’s the statute of limitations ran out on his crimes, he opted to write a book to tell his story which includes how he stole an Olympic gold medal from Johnny Weissmuller and then gave it back because he felt bad since the guy worked so hard to get it.

5. Natwarlal

The one man Indian crime spree known as Natwarlal had a Houdini-like ability to escape from just about anywhere. Ten times he had been sent to prison and 10 times he managed to escape. He’s risen to the level of folk hero in India, so much so that it’s impossible to tell how much of his life is fact and how much is fiction. There are numerous stories about his upbringing and family background, with no way to verify any of them.

His life of crime was as a con man. He was adept at forging signatures and manipulating people to get what he wanted. At one point he even managed to bribe one of his jailors with a box of money to set him free. After he left the prison, the jailor discovered that not only was the box of money not legitimate, but it burst into flames somehow as well.

So what got him sent away? His incredible ability to dupe people into believing just about anything. Word is that he sold the Taj Mahal more than once. Also, the Parliament House. Also the Red Fort, and several other major Indian landmarks that anyone listening to him should have known he didn’t own. But that’s how good a con man he was.

When not selling landmarks he was conning store owners, bankers, jewelers and more out of money and valuables. Interestingly enough, it’s also said that he would give back a lot of the valuables he stole to the less fortunate in his neighborhood.

Although he had been convicted in literally dozens of cases, he still managed to find ways to skirt the law. In 1956 a flood in one town washed away his entire police record. Every time he was caught he could somehow manipulate one or more guards into believing that he would pay them money if they would help him get out. Every single time they fell for it.

Even Natwarlal’s death is shrouded in mystery. Some sources say that he died in 1996. Others say it was 2009. 

4. Charles Sobhraj

Charles Sobhraj was not just a bold thief and con man, he was also a serial killer. He started committing crimes in his teens and discovered when he was in jail that he had a knack for manipulating others. He was able to charm the guards and other prison officials to grant him special favors.

Once out on parole, his criminal lifestyle escalated. He had a series of relationships with high-profile socialites in Paris, but continued stealing at the same time. After serving time for stealing a car, he left France for Asia and spent his time robbing tourists. He headed up a car theft ring in India and took up smuggling as well.

In Kabul he continued robbing tourists before heading on the run throughout the Middle East. At one point even swapped identities with his younger brother, letting his brother take the fall for him and getting an 18 year prison sentence for his troubles.

By the mid-1970s, he had committed his first murder and was actually leading something of a small cult of followers that he had charmed into doing pretty much whatever he said. He would poison people unbeknownst to them and then show up as the hero to nurse them back to health, gaining their loyalty in the process. Some of the people didn’t survive. 

3. Vjeran Tomic

Vjeran Tomic earned the nickname Spider-Man after committing numerous burglaries, but it was an Avengers-level art heist back in 2010 that made him famous. He managed to steal five paintings with a combined value of $110 million. That included a Picasso and a Matisse.

In his youth, Tomic  prowled Pere Lachaise, the famous French cemetery where luminaries like Oscar Wilde and Jim Morrison are interred. Before parkour was a thing, Tomic was scaling the massive mausoleums and tombstones just for fun. It was the skills he honed doing this that he would use later to climb up the walls of apartment buildings and break into homes to steal valuables. He claims to have stolen gold buttons from the Egyptian royal family at one point.

Some of his crimes were full-fledged Mission Impossible-style endeavors. In the year 2000 he fired a crossbow with a rope on the end of it at an apartment and used carabiners to climb up where he stole two Renoirs and several other important art pieces worth over a million euros.

2. British Bank Heist

When it comes to epic heists in history, you’d be hard-pressed to find one more impressive than the British Bank of the Middle East. In 1976, as the Lebanese Civil War was bearing down on its first anniversary, some enterprising thieves noticed that the British Bank shared a wall with a Catholic Church. As the instability of the country was causing turmoil, the thieves broke through the wall and then into the steel reinforced walls inside the bank. The sounds of civil war drowned out any noise they were making so nobody noticed.

Inside the bank’s vault was cash, jewelry, and solid gold bars. $300 million was taken. Adjusted for inflation, it’s over $2 billion. And not a single red cent was ever recovered. None of the criminals were ever identified, they were no leads, the thieves got away scot-free from what the Guinness Book of World Records describes as the biggest bank robbery in history.

1. Dar Es Salaam Robbery

When it comes to bold moves, the thieves who stole nearly $300 million from a bank in Baghdad back in 2007 really take the cake. The thieves in this case were the three guards whose job it was to guard the money in the first place. As part of that job, they were meant to spend the night in the bank. It was expected that they would actually sleep there, presumably in shifts. Instead, when employees showed up in the morning, the doors were open, the guards were gone, and so was all the money.

No one was ever able to explain why the bank had $282 million in American currency on hand at the time,  but it likely had something to do with the precarious financial infrastructure in Iraq at the time. The country was in utter chaos, and word is that 18 people in the city had been murdered on the same day. Police were pushed to their limits, and even stealing a huge sum of money could have easily gone unnoticed. Since the robbery, neither the money or the fees have been heard from.


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