The Gutsiest Criminals Of All Time

These criminals are special for one reason: They went to ridiculous measures to pull off their crimes. Some of them ventured into the realm of cross-dressing, while others were so fierce that they spat in the face of the government and won. Each case is different—and significantly weird—but they all have something in common: Guts.

Bank robber dresses as Santa

Finding out that Santa isn't real is a difficult time in a child's life. Finding out that Santa is a bank robber, though, has got to be worse. This is what happened in Texas on December 23, 1927, when a line of merry children followed a criminal disguised as Santa Claus right to the bank he was going to strike. The robber's name was Marshall Ratcliff and he had already been arrested for bank robbing before. But this time was different. This time, it was near Christmas, and he had genius on his side. No one would suspect Santa, would they?

Wearing his new outfit, Ratcliff quickly met up with his three associates and charged the bank at gunpoint. While the three accomplices were threatening the people inside the bank with firepower, Santa stuffed as much cash as he could into his sack. The cops were soon alerted to the crime, which resulted in a firefight between the two groups. After several more shoot-outs and car chases, the criminals were finally taken into custody. Ratcliff received a sentence of life in prison but then pleaded insanity, which the court system began to believe.

Frustrated by the slow-moving hand of justice, the citizens of Eastland County decided to act on their own accord. As a mob, they rushed the jail where Ratcliff was being held and took him out to execute him. As Murphy's Law would have it, all that could go wrong did go wrong when the first hanging failed and the mob had to try a second time. Santa was then successfully lynched. November 19, 1929, was the day the people killed Santa.

The Gardner Museum heist

The 1990 Isabella Stewart Gardner Museum Heist in Boston began with a criminal duo disguised as cops. A simple idea like that was enough to fool everyone and make for the biggest art heist in history. The fake policemen managed to be convincing enough to make museum guard Richard Abath walk away from his station and away from the alarm that he should have pressed. The still unidentified pair stole 13 works that belonged to the museum—pieces by famous artists such as Degas, Rembrandt, Manet and more. This piece pictured here is one by Manet called Chez Tortoni, circa 1880, that was stolen from the museum's Blue Room.

The Gardner Museum's current director of security, Anthony Amore, told Boston Magazine, "People say this was so elaborate. It's not elaborate! It was kind of a flimsy plan that worked." Perhaps that's what makes this crime so impressive. In total, the pair made off with $500 million worth of artwork. Despite their "flimsy plan," the FBI are still on the hunt for the thieves.

The Harry Winston jewelry heist

Every lady loves a diamond, right? Well apparently the same applies to crossdressers, because that's how four men pulled off an enormous jewelry heist at Harry Winston's in Paris in 2008. Three out of the four criminals masqueraded as posh females, wearing dresses, scarves, sunglasses, and blonde wigs, while the fourth man strolled alongside them into the store. What wasn't very ladylike was when they started pulling out hand grenades and revolvers and breaking glass cases to get their manly mitts on the jewels.

The group exited the building with over $100 million of plunder. It took years, but in 2015, eight men were arrested in connection with this heist and others that had occurred at Winston's in other years. However, despite catching a handful of criminals, law enforcers still have not found the majority of the loot taken, so someone out there is presumably still wearing them and looking very pretty doing so.

Madame Cheng and her pirate army

If you've watched Pirates of the Caribbean: At World's End, you'll remember that one of the pirate lords was a scary woman by the name of Mistress Ching, played by actress Takayo Fischer. What you might not have known is that the character was based on a real pirate. And not just any pirate—the most badass female pirate in history.

Her name is spelled in many ways in English, as the pirate herself was Chinese, but for the sake of ease and clarity, we'll refer to her as Madame Cheng. She started out as a prostitute, but she soon became the wife of a hugely successful pirate, Cheng I. He presided over the biggest pirate army in history—up until that time, at least. When he died, Madame Cheng took over for him and became even more notorious and seaworthy than he was. She increased the pirate army to 70,000–80,000 men by the year 1810, had strict command of all of the South China Sea, and chopped the head off anyone who disobeyed her orders. Her list of skills and accomplishments (moral or not) could easily go on for several more pages.

The emperor and his ilk could not defeat her in battle, so instead, the government sought to subdue her with a full pardon. At first, she declined, but later, she approached the governor of Canton with a renegotiated deal wherein she gave up her ships so that she and most of her crew could walk away with full pardons and also got to keep the valuables they'd taken. Not only did she get to be the fiercest female pirate who ruled over the largest pirate army ever seen, but she came out of it like a winner. To add insult to injury, she then opened up an opium den, a gambling house, and a brothel. She slapped the government across the face, and they thanked her for it.

Casino robber returns to casino to play

Sometimes, it's not about what happens when you commit a crime that's most exciting but what happens after. A perfect example of this is when Tony Carleo robbed the famous Bellagio Casino in Las Vegas in 2010. Leaving his motorcycle parked outside the casino, ready and waiting in the direction of escape, Carleo entered the Bellagio with little besides a gun and a bike helmet to cover his face. Once he zeroed in on a table in the casino, it was just a few moments before he swooped in and took what he would later count to be $1.5 million in chips.

Pulling off a casino robbery of that magnitude was crazy enough, but Carleo was going to prove how gutsy he could be the very next day when he walked back in to the same casino in plain clothes, this time unmasked. Nobody realized who he was. He walked freely about the building and even checked himself into one of the casino's hotel rooms. Carleo upped the ante even more when he repeatedly went down to the casino and played at the same table he'd robbed, each time slyly cashing in part of his stolen chips for cash.

After briefly living the glamorous millionaire lifestyle of sex, drugs, and expensive goodies, Carleo was finally caught by FBI agents thanks to a poker dealer who paid close attention on the job. The dealer had hosted the then-broke and devastated Carleo at his table right before the robbery and noticed when the same man came back days later, this time with his luck suddenly completely turned around. Carleo received a nine-year sentence at Nevada's Lovelock Correctional Center, but not before he made the ultimate gamble by hiding in plain sight.

The armored truck revenge robbery

Adnan Alisic was a man who got sucked down into the gambler's rabbit hole. He destroyed his business and racked up debts because he couldn't stay away from the tables inside the Casino Arizona in Scottsdale. His losing streak was running him into the ground, until one day, he managed to get extremely lucky and hit $60,000 on a blackjack table. But before he could try to up his winnings, security banned him from the casino. Alisic decided to strike back.

He made himself extremely familiar with the routine of the casino's armored, money-carrying trucks and knew what time they came in and with how many guards. Not wanting to get real weapons involved for fear of getting shot himself or accidentally shooting a random bystander, he bought fake AK-47s. He and his accomplice, a friend named Ismar Kabaklic, grabbed their fake weapons and ambushed the armored trucks just as they were being opened. The two pepper sprayed the guards and threatened to shoot if they didn't cooperate.

Once they fled with the cash, the robbers drove their van to a place they knew had a network of tunnels beneath. They were to head down a manhole and escape, but not before putting the van back in gear, this time with blow up doll and a fake gun in the driver's seat. However, the plan collapsed when the fake cover they'd put on the manhole prior to the robbery refused to lift out of place. Suddenly, they had to find another way to escape and fast. They got back in the van and just drove.

In the end, their manic car chase with the cops resulted in both criminals being arrested. Alisic got 17.5 years in jail, while his partner got six and a half. The blackjack addict went bust yet again.

A deadly scavenger hunt

They call it the Collar Bomb Heist, and it was the worst scavenger hunt ever. In 2003, a pizza delivery guy was pawned into a bank robbery scheme that ended up taking his life. His name was Brian Wells, and he had a bomb rigged and ready hanging from his neck. His first order was to steal $250,000 from a bank in Erie, Pennsylvania. After he left the bank with only a small portion of what he asked for, cops caught up to him, and he revealed that this whole thing was not his idea—he was innocent. But before the bomb squad could arrive on the scene, Wells's death trap went off, killing him on the spot.

What was left for the police was a series of clues, each leading to a new one that took them all over town. The handwritten clues took the police to a McDonald's flowerbed, to a particular street sign, and all the way into the woods. They chased these clues but got no answers from them, wasting time as they went. Law enforcement was extremely puzzled, especially when they began to get strange tips that led them on another scavenger hunt of sorts for the mastermind of this whole ordeal. Blame was placed on several people, all pointing fingers at one another and claiming they knew about the robbery but didn't take part in it. In the end, a woman with a record of acquitted murder charges, Marjorie Diehl-Armstrong, was sentenced to life in prison, and those she used to help her achieve her ends, like crack dealer Kenneth Barnes, received reduced but still lengthy sentences. It was also revealed during trial and investigations that the pizza delivery guy from the very beginning was also in on the plot—he just didn't think he was wearing a real bomb.

However, while it seems like all loose ends were tied on the Collar Bomb case, one man believes the justice system got it all wrong. Jim Fisher, a retired FBI agent, began to obsess over the crime and his version of the story is that one of Diehl-Armstrong's conspirators, the late Bill Rothstein, was the man behind it all. Fisher also claims that Rothstein, who died before ever receiving a conviction, put this whole scheme and scavenger hunt together just for the hilarious thrill of frustrating the cops with his complex riddles and causing mayhem for everyone around him.

Steal plane, go to concert

There are lots of ways to celebrate the Fourth of July. Most people commemorate the United States' independence from mother England with a barbecue, a fireworks show, and maybe a flag cake. Chicago rapper Famous Dex decided to throw a big holiday concert in his home state of Illinois, and 18-year-old Zemarcuis Scott of Arkansas decided he absolutely had to be there to see the rapper perform "Japan" and "Pick it Up" live. And so, he tried to fly there. But he didn't buy a plane ticket or anything — instead, he attempted to steal a plane from the Texarkana Regional Airport.

In the early morning hours of July 4, 2018, security guards at the airport noticed Scott jump a fence. They called police, who discovered Scott sitting in the cockpit of a small, twin-engine commercial jet. It's worth noting that Scott is not a licensed or even trained pilot, and he told detectives that he figured he could fly the plane by (pardon the pun) winging it and just messing with various buttons and levers and such.

Scott pleaded guilty to charges of attempted theft of property and commercial burglary. He was fined, given five years of probation, and ordered to undergo mental health treatment. But there's a happy ending: When Famous Dex heard about the measures Scott took to see him, he offered to fly him out to Los Angeles for an upcoming concert (with a real pilot behind the controls, presumably).