It’s been said that crime doesn’t pay—but maybe that’s just for criminals who don’t know what they’re doing! Granted, these people are choosing to use their skills for bad instead of good, but it's still hard to not be impressed by their unique levels of skill and intelligence. Here are 42 incredible stories about some of the most clever criminals of all time.
I used to work at a jail. After getting off of work one day, I watched a homeless ex-inmate being released. He walked right over to a patrol car, looked me in the eye, and the elbowed the window in. He was promptly walked back to the entrance and re-booked in. It was the middle of January. He didn't want to get too cold.
I heard a story of a guy who was driving drunk and passed a cop on a bend. So, he immediately parked his car and threw his keys into the woods. Then, when the cop came over, he quickly downed an entire bottle of vodka in front of the cop. Since he didn't have his keys, he didn't have the ability to drive—and since the cop had just witnessed him drinking outside the car, he couldn't check whether he had been drunk when he was actually driving a few minutes earlier. The cop had no choice but to let him off with just a warning.
I knew this guy back in the early 80s. Let's call him Jim. Well, he really wanted this high powered superbike, but he also knew that he could never afford it. So what did he decide to do? He drove all the way to London and scouted about for a few days until he finally found that particular model of bike parked outside of a house.
He goes back that night with a slide hammer, pulls the lock off, and steals the bike. He gets it home, puts it in his garage, and completely strips it down so that the only thing left on it is the frame and the bottom half of the engine—which he then drags into the weeds at the bottom of his garden, pours fuel all over, and burns.
A few weeks pass and weeds have now started to grow over it. It's at this point that he calls the cops and reports that someone seems to have mysteriously dumped a bike frame in his garden. The cops show up. He explains to them that he had just gotten back from being out of town, and had unexpectedly discovered these remains in his yard upon his return.
The cops take the frame and note down his name and address. A few days later, the cops call him and explain that the bike had been stolen from London a month or so ago. They also explain that the insurance company had classified the bike as a write-off, and had asked the cops to dispose of it for them. NOW...
Because the frame was found in his garden and the insurance company didn't want it, the cops were duty bound to ask him whether he wanted to keep it or whether they should just throw it away. So, he thinks about it for a moment and then tells them that he has always wanted to build himself a bike...He gets the fame back from them, repaints it, and then puts it all back together and re-registers it as a "Q" reg (meaning stolen and recovered). Oh, I forgot to call him Jim, didn't I?
The smartest criminal I've ever heard of was the guy who stole about $12 million worth of diamonds, stashed them away somewhere, and then turned himself in knowing that there was a maximum sentence of just two years for that crime. You get the idea.
A friend of my brother’s had moved to Israel, where for a period of time it was legally acceptable to drive with only an American driver's license. One time, he got pulled over by a cop for speeding. When asked for his license, he gave the officer his Costco card. Apparently, most countries don’t have Costco and, therefore, most people outside of the US aren’t familiar with the retail chain.
The exchange that followed apparently went something like this: Officer: "Costco? What is Costco?" Friend: "It's the state that I'm from." Officer: "That sounds made up." Friend: "There are lots of small states that you probably haven't heard of. Have you heard of Arkansas? How about Idaho?" Officer: "I guess not..." Friend: "Well, I'm from the small state of Costco."
The officer didn't have a response and wound up writing the ticket to someone with a Costco driver's license. My brother’s friend framed the ticket and still has it hanging on his wall to this day.
I’m a warden. I once dealt with a criminal who successfully forged a series of court documents facilitating his own release from prison.
I don’t think that anyone will ever be able to match the level of criminal genius achieved by the infamous Victor Lustig. He successfully “sold” the Eiffel Tower to some scrap metal dealers in 1925 by posing as a government official and claiming that France was planning to take the structure down due to the fact they could no longer afford to maintain it.
There's a small tourist town near where I grew up that is divided in half by a big river. The only way to get back and forth between the two sides is over a long bridge, unless you want to go all the way around to another mountain pass. These guys once called in about two or three bomb threats to a posh hotel on one side of the bridge. I think they even left some decoy packages at the scene, too.
All of the police immediately went across the bridge to do crowd control, etc. Meanwhile, the guys who were responsible for the calls started robbing stuff back on the other side. The police couldn't be absolutely certain as to whether the bomb threat was real or not, and they hesitated for just long enough to give the thieves the head start they needed.
H.H. Holmes was a conman and one of the first known modern serial killers, who remained an active criminal for many years until he was finally caught. If I remember the story correctly, he built a giant hotel full of secret passageways, false walls, and trap doors during the Chicago World's Fair in 1893. He had a lot of fun with using different and creative methods of killing people—and you can tell that he really loved what he did.
He collected skeletons from his victims and had them processed and sold to medical schools, which turned him a big profit. It was estimated that his "Murder Castle" killed around one hundred people in total. He was basically a real-life version of the classic evil genius type of character. "I was born with the devil in me. I could not help the fact that I was a murderer, no more than the poet can help the inspiration to sing—I was born with the 'Evil One' standing as my sponsor beside the bed where I was ushered into the world, and he has been with me since."
A French thief who spent ten years in prison became a comedian when he got out. One of his favorite stories to tell is of the criminal who found an apartment building, went in, chose a random floor, and completely transformed the exit door to look like the door to an apartment. He put up an apartment number, a fake lock, a welcome rug—everything you can imagine.
He then put an iPhone up for sale and advertised this fake apartment as the address to come and buy it at. So, a customer came to buy it, he opened the door in a shower robe, took the cash, and asked for a few seconds to just count the money while he went to go grab the phone. As soon as he shut the door behind him, poof! He disappeared down the exit stairs with the guy’s money before he could even know what hit him.
John Dillinger, the famous mobster, was quite an incredible case. The public absolutely adored him despite his violent criminal streak. Even though he wasn't unique in that regard (since the public also loved Al Capone and company, at least until the Valentine's Day Massacre), and even though he was active during the Great Depression when opinions were rather easily swayed compared to usual, I still think it's pretty cool that he managed to achieve and maintain that kind of reputation.
He had his cohorts impersonate police officers to break him out of prison. He used hostages as human shields. And through all of this, he never lost control of his public image! Of course, I'm not condoning or celebrating what he did, but I just can’t help having his name pop into my head when I think of the words "criminal mastermind."
I don't know if this one was necessarily the most clever in history, but back in 2007, one František Procházka stole more than half a billion in Czech Crowns cash (equalling over 20 million EUR at the time) from a very well known security agency—and he basically just walked right out the door with it. The guy had actually been working at the company.
It’s been said that right from the beginning, he had planned on getting a job there, specifically so that he could be familiar with exactly how everything worked on the inside right down to the last detail. On the day of the robbery, his partner drove up in a van marked with the logos of the company. They loaded the cash into the back and drove away.
His accomplice was caught and, if I remember correctly, sentenced. Procházka still hasn't been caught yet as far as I am aware. The closest they came to catching him was three years ago, when he was spotted in the Dominican Republic. He still managed to get away in the end, however, and he remains at large to this day.
A homeless guy in my hometown figured out that if he committed some act of petty theft, he'd get a free night in a cozy jail, a warm place to sleep, and a hot meal. He'd then show up, turn in his stolen goods, and that would be that. After a while, the police caught on and would just go along with it as long as he agreed to take back whatever he stole the next day. He was quite the town character!
The smartest criminal I’ve ever heard of is Arno Funke, alias Dagobert.
For those who don’t know, Mr. Funke was a man who repeatedly extorted and demanded ransom payments from department stores in Germany in the early 1990s. There were over 30 times where he successfully extorted a place and collected money from them. He frequently used technical devices, or even bombs, to fool the police and remain on the loose.
As an example of what he used to do, he once asked for the money to be deployed in a box that was attached to a train. The police found a time control mechanism that was set to detach the package from the train at a specific time and place. They found out when and where it was programmed to detach, and they positioned themselves at the expected location.
However, Funke had also installed a radio control device so that he could detach the package manually from the train whenever he wanted to, and he successfully did so much earlier than the police had anticipated. Basically, no matter what the police thought of to try and catch him in the act, he was already a step ahead of them and able to foil their plans each time. He was finally caught after six years of these antics and has since become a popular author.
I’m a police officer. I once had a guy use a sledgehammer to smash his way through a wall at a Best Buy and steal a bunch of phones and cameras. He was smart enough to wear gloves and a face mask and to not touch anything that he didn’t have to. The alarms didn’t go off until he exited out the back door. The alarm company only gets notified of the alarm after a minute or two, and it then takes them at least three to four minutes to evaluate the situation before calling in to us, giving the guy a solid five-minute head start before we were even aware that anything was wrong. He was probably already a few miles away before we got dispatched to the scene. He had clearly scoped out the area before doing his deed, too. Smart dude.
I'm not an expert, but I would say that D.B. Cooper definitely deserves a mention. That dude hijacked a plane, got a bunch of ransom money, and released all of the passengers. Then, he had the plane take off again and parachuted out the door in the middle of its second flight. He was never caught.
As a police officer, I can honestly say that any criminal who immediately requests a lawyer prior to questioning is as smart a criminal as can be. That is definitely the smartest thing you can do if you have committed a crime in almost any scenario. If you speak with me and confess, you're screwed. If you speak with me and lie, you're screwed. If you say nothing at all, there's a chance that I will end up being screwed.
In Argentina, there used to be a prominent corpse-kidnapping gang. They targeted rich people's dead relatives and would dig up and kidnap their coffins. Of course, they were eventually caught after a long string of successful corpsenappings. The story was that since a corpse is neither a living person nor private property, there were no laws on the subject—and so what they did was not actually illegal. Therefore, the police could do nothing about it, yet the relatives obviously cared about their loved ones’ remains and would often be willing to pay big bucks to get them back. Now that’s what you call a creative criminal!
There was this guy who found himself in heaps of debt, as in more than a lifetime’s worth of debt that there was no way he could ever repay. He proceeded to file several police reports for identity theft, up to the point where he got protected from financial checkups. This was a temporary measure that was often given to repeated identity theft victims.
At the same time, he had reported fake income to the IRS for the last couple of years—showing something between $40 and $60 million, depending on the year. So, when he applied for credit cards and loans, banks were unable to check his financial credit due to the identity theft protection—but when they checked his tax returns, they saw that he had a massive income. He got all of his loans and credit cards, emptied them out, and quickly left the country.
The smartest criminal I know of would definitely have to be the guy who ate his own bank robbery note right off the hood of the police car while they were emptying his pockets. That’s definitely one way of removing the evidence! Although, the whole thing was caught on video and I'm fairly sure he was still convicted.
I know of a guy who sold thousands of fake raffle tickets to raffle off stuff that he never even had, and for raffles that he never even actually held. I can’t remember how many times he successfully pulled off that scam without being detected, but it was at least enough to buy a nice new car. He ended up moving towns a bunch of times because people would eventually start to suspect him of being a con man. His dad was apparently also in jail for having pulled somewhat similar stuff back in his day. Despite all of that, he was never even questioned by the police about anything. Now he has a family and a normal job from what I understand.
I think that Gerald Blanchard was the smartest criminal in history. He was a Canadian kid who began with hiding inside of the AC vents of banks so that he could clean out their ATMs overnight. He eventually made his way onto things like high-tech thefts involving parachuting himself out of a plane to steal a priceless piece of jewelry from a museum in Austria.
I worked in a home improvement store when I was younger. One day, this guy came in, went over to the snow blowers, took one, and went over to the return desk. He said that he wanted to return the item but had no receipt. They told him that he needed the receipt in order to do so, so he said “Fine, I’ll go get it and come back then.” He then proceeded to wheel the item off to his car through the front door. I’m told he apparently did this a few more times at various other stores as well. A couple of places even had staff members help him load the items “back” into his car.
I’m not a police officer or anything like that, but a relative of mine works for Border Patrol on the Texas border and he once told me about this hilarious experience of his. He was once out in the field when he and a couple of other officers caught this dude who had crossed the river naked. He had put all of his clothes in a plastic bag so that they wouldn’t get wet when he swam.
As they were walking him over to their vehicle, the guy kept complaining that he needed to go to the bathroom. Finally, they gave in and let the dude have some space to do his thing. They took a step back and faced away. The dude takes a squat and starts doing his business. Then came the plot twist. The dude caught his own poop with his bare hands and started smearing it all over his naked body.
The officers were totally shocked at this and did not know what to do. The dude took advantage of their surprise and started running his butt off back to the river. The officers were able to catch up to the dude eventually, but none of them went in for the grab or tackle because they didn’t want to get covered in some guy’s poop. The dude made it safely back into the river and talked smack the whole time as he swam back across to the other bank.
The running part lasted like ten seconds total, so I guess I don’t blame them for not being able to process the situation fast enough to react in time. It sucks that the dude got away—but at least every time my relative tells the story, he always has a smile on his face.
This was in the late 90s or early 00s. A guy in my dorm signed up for school solely for the purpose of dealing drugs. He took out student loans, registered for a bunch of 300+ person freshman survey courses where he would never be missed, then literally never went to class. All he did was go to raves, concerts, and keggers, and sell party drugs to everyone there.
After the first semester, he got suspended. He wrote the usual "I was young and dumb and in over my head" sob story, and got put on probation for a semester. So he then had a repeat of the fall. At the end of the year, he was kicked out—and didn’t care in the slightest. He made something in the ballpark of $150k, in exchange for about $8k in student loans to cover a year of housing and tuition. As far as I know, he was never caught. It may have been a short-sighted maneuver in the long run, but in the short run, it seemed fairly genius to effectively use federal loans to start your drug business.
Close to 20 years ago by now, a guy on Australia's Gold Coast got away with a major bank robbery in broad daylight. He had scouted out the bank for a while and discovered a pattern of the bank manager always arriving about 30 minutes before anyone else each morning. He would then routinely leave the front doors unlocked so that staff could easily let themselves in without a key or needing to wait for the boss to come and let them in.
One morning, the crook dressed himself up for a busy day of office work and waited for the bank manager to arrive. As the manager was unlocking the front doors, he made his move. He entered the building and threatened the manager with a gun. He got all of the details he'd need to access the vault and so forth, and then tied the manager up and stuffed him away in his office. When the rest of the staff arrived, he told them that the manager had called in sick that morning and that regional office had sent him in to do the open shop thing on his behalf. No one batted an eyelid at this story.
This bank had a small walk-in vault that normally only held about $30 to $50 thousand in it on any given day—but our old mate had intentionally timed his robbery for the morning after business banking day, when all of the local small businesses would make their end of the week deposits at once. The bank would reportedly bring in a score of close to $250 thousand on those days.
Once the vault was open, he pulled his gun out and invited all of the staff to enter the vault with him. He then proceeded to lock them all in. By this stage, the bank was already due to be open. So, when he went to leave, there were a number of customers waiting to get inside to do their banking. Still posing as someone who worked there, he told them all that there had been an issue with the computers and that the tech team had estimated it would take about 30 minutes before the issue would be resolved—and that they couldn't open the bank until that time.
Our friend then got into his car, drove straight to the airport, flew straight to Hong Kong, and was never seen or heard from again. To my knowledge, the cops have still never caught him even all these years later, and they never managed to find the money either. They do know, however, that he would have had to have left most of it in Australia somewhere, because you are only allowed to transport up to $10 thousand worth of cash in any currency out of the country without customs pulling you into their interview rooms to investigate and verify its origins. Therefore, the assumption is that he had to have had an accomplice here in Australia who has been funneling the money to him slowly over time ever since.
A guy once bought and financed a car. He then proceeded to never make a single payment. So, after 90 days, the repo men showed up looking for the car—but they couldn’t find it. Lo and behold, more than a year and a half later, an auto repair and customization shop files a "mechanics lien" on the vehicle for over $15,000 worth of custom rims, tires, upholstery, engine work, and a completely awful paint job.
Of course, the auto finance company is not going to just shell out 15K to get this now non-desirable car. So, they sign the title over to the mechanic, who just happens to gift the car back to the original owner. The original owner's credit is now ruined, but what does he care! He has a brand new car, which he had been driving after about six months of hiding it. Pure freakin’ genius…
My friend, who is no longer a criminal, used to grow weed in a shed on his neighbor’s property. The neighbor was an old person who never left the house, so he was able to successfully do this for years without ever getting caught.
It's hard to think of anyone who can beat the Zodiac Killer on this front. The guy left behind puzzles and killed enough people to get a nickname, yet we still have no idea who he is.
Back in the day, when there were casinos in Cuba, a man once bought two cases of playing card decks. He spent months carefully opening each new deck and marking each card in a way that no one would be able to notice. He then resealed the two cartons and sold them in the local flea market. Now, who would go and buy a whole case of cards—let alone two? The casinos, of course! After a while, he started repeatedly winning at poker in one of the casinos that had bought his cards. They pretty much knew that he had to be cheating, but they could never catch him switching the deck or doing anything to tamper with it. Very clever.
I remember getting into a festival and seeing a magician guy doing tricks on the police officers who were searching him, to distract them from finding the drugs he had on him. It was a spectacular show, and I’m sure he made a good profit.
One guy who happened to have drugs in his car got pulled over for an ordinary traffic stop. So, he tied the drugs to a balloon and let it go while the cop was still just approaching his window. The whole things was caught on tape. Now, that’s what you call thinking on your feet!
Dave was working at a Mercedes dealership. One day, he’s just sitting at his desk when this well-dressed gentleman comes in and asks if he can test drive a particular car that he had seen parked out in front. It was a very busy day at the dealership, and they had a policy that anyone could test drive a car on their own as long as they left some kind of deposit behind.
So, Dave gave the man the keys. The guy then went off on his test drive, and came back a reasonable amount of time later. He walks in, hands off the key, gets his deposit back, and goes on with his day. This was just before closing time, even possibly on a Friday. Everything was in order at that point. Fast forward to the next business day. Dave's boss walks in and realizes that a Mercedes from out front is no longer there. Dave has to explain that the car was returned and that they have the key and everything.
Turns out the criminal didn't really take it for a test drive. He had just driven it somewhere to have a replica of the key created. He had then given that replica back to the desk, while keeping the real key for himself. He returned over the weekend to take the car when no one was around. That smart son of a gun!
I think that the Isabella Stewart Gardner Museum thieves in Boston are the smartest criminals of all time. In one of the most famous museum heists of all time, they got away with paintings worth over $500 million, and were never caught.
An ex-criminal I know today once got away with buying a building under a fake name, taking out huge loans against it, getting government money from the Department of Housing and Urban Development, and then burning it all down and disappearing without a trace.
I think my personal favorite is the story of the Japanese bank heister who dressed up as a cop. If I remember correctly, the story went like this: A bank manager in Tokyo and his employees had repeatedly been sent threats in the mail for the past few months. Then, one day, a letter arrived in the mail at the bank manager’s house, demanding a payment of 300 million yen. The letter also said that if he did not comply, his house would be blown up.
Security was immediately ramped up and most of the bank’s employees were put under constant watch by the police. As they continued working for the next few days, the bank manager had sent four employees out to go make a regularly scheduled delivery to a nearby factory. As they were on their way over, they suddenly heard police sirens approaching them.
A cop on a bike pulled up and told them that the manager’s house had just been blown up and that their vehicle now needed to be checked for explosives. As the cop went underneath the car, the employees suddenly saw a thick white smoke begin to emerge from the hood of the vehicle. Naturally, they all immediately ran away from the car to seek cover.
They waited nearby for an explosion or for some kind of indication that the situation had been resolved. Minutes passed, and nothing had happened. After about ten minutes or so of waiting, they finally walked over to check—and they discovered that their car was gone.
Apparently, the man was not actually a cop, but was just the guy who had written all the letters dressed up as one. He had planned this whole thing from the start, and had just lit a flare underneath the car to scare them into running away. A total of 300 million yen was inside the car when it was stolen—exactly the amount that the demand letter had requested.
There's a golf course and country club in my town that is hoping to have an upcoming PGA tournament scheduled to be held there within the next couple of years. They also now have a guy who has been repeatedly breaking in overnight and just lounging around with his friends or eating food from the clubhouse, all while clearly on camera. He knows that the club will repeatedly refuse to report it so as not to incur any controversy that could potentially hurt its chances of being selected to host the tournament.
My story goes like this: A homeowner walks out one morning to drive to work, only to find his car missing. He reports the car as stolen to the police. A few days later, he walks outside to find his car sitting back in front of his house again as if nothing had ever happened. Upon closer inspection, he finds a note inside.
Turns out it was an apology letter from the thief, explaining that he had been in dire need of quick transportation and so he decided to "borrow" the first car that he could find with the keys inside. The note went on to say that the thief had noticed the bumper sticker on the back of the car for the local sports team.
Just so that there were no hard feelings, he explained, he left four tickets to an upcoming game in the glove box for the homeowner and his family to enjoy. So, the homeowner and his family attend the game and have a great time. They then return home to find that the house has been ransacked, and all items of value are now gone.
Most criminals that I’ve seen have been really stupid, so this guy is by no means a criminal mastermind or anything like that. Nevertheless, he was—even if by default—the smartest criminal I’ve ever seen, so here goes. He wanted to rob a jewelry store on our city's main street. So, he found out that the flat beside the jeweler’s was empty, and he hid there.
For two weeks, he triggered the alarm on purpose several times a night, causing a massive headache for the police and the business. Each time, we turned up to find nothing there and nothing on the cameras. Naturally, we all just thought it was some kind of a fluke, so the jewelers turned off their alarm system to avoid it happening again, saying that they would wait until the morning to get a new one installed.
As soon as he heard that, and as soon as the police left the scene, he tore down the wall and robbed the entire place—even taking his sweet time in doing so. He escaped without anyone noticing anything for hours, until the jewelers came back in the morning. Where it all went wrong was when he tried to re-sell something that he had stolen back to the store, not realizing that it had a serial number on it. He got caught pretty quickly. Soooo...I guess he was not that smart after all. He definitely gets an A for effort though!
I locked up a guy a few years ago and I noticed that he had an unusual crime on his criminal history: "Theft of an ATM." I asked him about it. He told me that he and four other guys once turned up at a local bank in overalls with a large truck. They asked for the manager and told him “We're here to repair the ATM machine.” The manager actually helped them load the ATM onto their truck, cash and all still inside, and they then drove away without any issue or suspicion. When his girlfriend found out what he had done shortly after, she got mad and turned him in.
I was an RA in college. My university owned all of the houses adjacent to the campus. These were run like dorms, with RAs and all of the same rules—including a very strict no alcohol policy. It was a privilege to live in the houses and priority was always given to upperclassmen, who were more likely to bend that rule because they were of age and it was harder to police people off campus in houses.
There was a student who went around knocking on doors saying something like “I’m an RA and I’ve been sent over for health and wellness checks.” She’d then find their booze, take it, and follow up with a speech about how she’s doing them a favor by just giving them a warning. She wasn’t actually an RA and was just keeping the booze for herself.
The only reason she got found out was that she accidentally did it to an actual RA one time. At first, the RA had just assumed that he didn’t know her. It was only later that he began to question why they had a female doing wellness checks on male housing. They did an investigation and asked other residents about it. They discovered that there had been incidents dating back as far as two years previous. They were never able to find out who she really was.
There was a guy with over 50 unpaid speeding charges. He went by the name of “Prawo Jazdy.” Each time, he had been in a different car, with a different disguise—so no one had ever been able to pin him down. Eventually, after the government set up a special task force to try and take care of this guy once and for all, they realized that “Prawo Jazdy” just means “driver’s license” in Polish.
Yes, that’s right. The government didn’t realize that this alleged criminal mastermind was actually 50 different unrelated people who just happened to all be from Poland. The police had just accidentally written down “Prawo Jazdy” as a name every time that someone with a Polish driver’s license was caught speeding.
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