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Police Officers Talk About the Smartest Criminals They’ve Ever Encountered

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It’s been a permanent fixture of film, television, and literature for years. The cunning criminal who is so bright that they routinely outsmart the police and make them look foolish.

But this phenomenon exists in real life too, believe it or not.

AskReddit users shared their stories about especially smart criminals.

Let’s see what they had to say.

1. That is insane.

“My favorite was the guy who stole a post office mailbox off the street, repainted it, and then put it next to the night deposit box at a bank.

And hung an out-of-order sign on the deposit box. All the businesses came along and dropped off their deposits in the mailbox.”

2. Ahhhhh, the GPS.

“I worked crime scenes. This guy had attached GPS to the bottom of peoples cars who owned houses, he wanted to rob.

He did it to ensure they wouldn’t be showing up while he was ransacking the place.”

3. Almost got away with it.

“I remember an officer telling me about a B&E alarm he and his team responded to. No one was there to report the alarm, it must have been a security monitoring company that called.

When police showed up, everything seemed normal, most lights were off, and there was an employee still working. Explains he was there working late and must have set off an alarm.

They almost believed him until he said “uhh” before saying the name of the company he worked for. After that it was downhill but with a little more research he would have pretty much gotten away with it.”

4. On parole…

“There’s one guy I recently dealt with who is on parole. I stopped him in my city after he was looking to buy drugs (usually people come from all over to buy drugs and then leave). I issue him a warning and let him go as it’s pretty common and he sang like a bird regarding the people he was trying to buy from.

Anyway, the next day, I got a call from his parole officer who says he was alerted the guy was pulled over and wanted to verify that It was his guy that I stopped. I’m a little confused at first but he goes on to say that the day before, he was scheduled to meet with him but he had an excuse and bailed.

His excuse was that he was in the hospital. Well when he spoke with him the following day, he was able to provide documentation that he had entered the hospital day 1 and had left day 2. Well I had stopped him at 115 in the morning and after looking at the picture, it was 100% him.

Turns out the guy had checked in then out of the hospital on day 1, then in and out again on day 2. He then re arranged half the paperwork to make it look like he was in the hospital overnight which would make my car stop of him appear like I mixed him up with someone else as well as give him a valid excuse to miss their meeting.

Not sure what’s gonna happen to that guy but I thought it was pretty clever.”

5. It’s cold outside.

“Worked at a jail. After getting off work, I watched an ex inmate (homeless) being released, he walked over to a patrol car, looked me in the eye, and the elbowed the window in. He was walked back to the entrance and re-booked in. It was middle of January. He didn’t want to get too cold.

To the people talking about “Can’t break car windows.” That’s true. Also depends on the car. The patrol car they used was specifically old model. Used more for the perimeter of the jail unless other patrol cars were in the shop. Those windows had been replaced so many times. Idk if it’s the same material or what.”

6. The great state of Costco.

“A friend of my brother moved to Israel where for a period of time it was/is acceptable to drive with an American driver’s license.

He was pulled over for speeding, and when asked for his license, gave the officer his Costco card (Costco is a membership-based retail warehouse in the US and a few other countries. The exchange apparently went something like this: Officer: “Costco? What is Costco?”

Friend: “It’s the state I’m from.”

Officer: “That sounds made up.”

Friend: “There are lots of states 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. Friend framed the ticket and still has it hanging on his wall.”

7. It all adds up.

“One guy would print barcodes, bring them into home depot and stick them on merchandise in the $100 range. When scanned the items came up around the $10 range. Putting random barcodes on things isnt really illegal and super hard to notice. Guy two would come in an hour later and buy the underpriced stuff. Complete plausible deniability. They would then sell the stuff on Ebay.

Only reason they got caught is because the guy with the barcode printer/software cut the second guy out of the operation so guy 2 stole a bunch of barcodes, put them on the merchandise and paid for it immediately afterwards. He then proceeded to rat on the first guy and spilled the beans they had been doing this on a weekly basis for over four years.

Because we could only pin the one case on him, the burglary was dropped down to a pretty theft and he walked away with a few days in county and a small fine. Dude probably took homedepot for tens of thousands over the years.”

8. Fraud!

“I have a nice story from insurance/debt collectors.

There was this guy who was already in heaps of debt. Like more than a lifetimes worth of debt.

He proceeded to file several policereports for identity theft up to the point that he got protected from financial checkups – It was a temporary measure that were given to repeated identity theft victims. At the same time he had reported fake income to the IRS for the last couple of years to between 40 to 60 millions depending on the year.

So when he applied for credit cards and loans, they were unable to check his financial credit (Due to the identity theft protection) but they checked his tax returns which showed he had a massive income.

Got his loans and credit cards – emptied them out and left the country.”

9. Very clever…

“A while back, there was a series of thefts along the bus lines in my country. People’s things kept missing from one city to the next, and nobody had any idea what happened as things were presumably safe in the bottom of the bus which nobody except the driver had the access to.

What happened?

Apparently there were two guys, one of whom was really small. You get where this is going. The big guy would put the little guy in a suitcase, buy a ticket to somewhere, load him up with the rest of the luggage, and enjoy the ride, while the little guy went out, stole people’s electronics, jewelry, cameras and whatnot, then returned to his suitcase until the ride was over.

Not really sure how they caught them, but it was pretty amusing to read about, and i found the whole thing clever enough.”

10. This guy wasn’t messing around.

“There was an incident in Fargo ND where a guy wanted to steal electronics equipment. The store had plenty of alarms on it and generally cutting an alarm triggers an alarm so instead he cut ALL the alarms. This was before cellphones were really widespread and alarms were usually just connected to the phone line.

He found an access point to one of the phone companies big trunk lines (correction: 9 access points). Massive thick copper cables with tens of thousands of lines running through them. He cut through the whole thing with a circular saw, knocked out phone service to most of the town and robbed an audio store during the ensuing chaos.

There were no leads until a tip came in from another town where he’d pulled something similar. They hadn’t been able to pin that to him but had strong suspicions and he’d relocated to Fargo. So the cops pay him a visit. He refused to let them in because they didn’t have a warrant so the cops left to get one without leaving anyone to watch him and he split. When they came back they found the saw coated in copper dust and a lot of the stolen stuff.

He was in the wind for a while but even after he got caught he had another card to play. While being transported between prisons he used a key he’d made to unlock his shackles and climbed out the roof vent of the bus.”

11. In broad daylight.

“20 years ago a guy on Australia’s Gold Coast got away with a bank robbery in broad daylight.

He cased the bank for a while and discovered a pattern of the bank manager arriving about 30 minutes before anyone else each morning where he would leave the front doors unlocked so staff could help 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 doors he made his move, entering the building and threatening the manager with a gun. He got all the details he’d need to access the vault and so forth and then tied the manager up and stuffed him in his office.

When the staff arrived he told them that the manager had called in sick and that regional office had sent him in to do the open shop thing and no one batted an eyelid. This bank had a small walk in vault that normally only held about 30-50k on any given day but old mate had timed his robbery for the morning after business banking day when all the local small businesses would make their end of week deposits and reportedly got a score of close to 250k.

Once the vault was open he pulled his gun out and invited all the staff to enter the vault and locked them in. By this stage the bank was due to be open so when he went to leave there were a number of customers waiting to get inside to do their banking.

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 until then.

Then he got into his car and drove straight to the airport and flew to Hong Kong and then disappeared.

To my knowledge the cops never caught him and never managed to find the money – they knew he’d have had to leave most of it in Australia somewhere because you can only take 10k aud in cash in any currency out of the country before customs pulls you into their interview rooms so the assumption was that he had to have an accomplice here who would funnel the money to him slowly over time.”

12. Never got caught.

“Several years ago in Cape Coral FL, a man waited on a sidewalk in front of a Publix grocery store and used a taser on an armored car guard carrying too bags of money.

A get away driver in a car with stolen tags pulled up, taser guy and money bags get in and they took off. Never caught.”

13. Small-town crime.

“Probably one of the smartest robberies in my small city.

One of the main streets is cut into a hillside and, as a result, there is a very steep and quite tall concrete-covered bank immediately behind the buildings. Between two buildings there is a gap that was filled at the street-end by an ATM.

To access it for filling, the security staff went through the next door building, out a side door and into the gap, which had the ATM at one end and the steep bank at the other. On the Friday before Christmas, when the ATM was to be filled to the brim, one of the robbers abseiled down the bank at night into the gap and waited for the guys to arrive to fill the ATM (they came early in the morning).

As they came through the door into the gap, he held them up, took the money, and took off through the building to an accomplice waiting in a van on the main street. Then the van took off on the main road out of the city and vanished.

After a big search, the police finally found the burnt-out van. Turned out the gang had driven it up a gorge road and had two other accomplices in cars at the top and bottom of the gorge who simultaneously drove really slowly into the gorge and held up the traffic so that no one was there to see them when they turned off down an access road into some bush.

They ended up being caught, because one of the gang was a former employee of the security company.”

14. Working the system.

“I worked with this one guy who had a lengthy record. He had a system for getting released if he got caught. After committing a crime, if the police were in pursuit and he knew he was about to be cornered, he would act insane.

His girl would play along with it telling the police that he was off his medication. The police would arrest him but then send him to a mental ward with papers instructing the ward to release to police once he was cleared. Once he was in the mental ward, he would cause a distraction that would make the person attending the desk with the file cabinet to leave said cabinet.

He would then crawl to the file cabinet, look for his “release to police” papers, and then would literally eat the papers. When the psych evaluators decided that he was stable enough to be released, there would be no instructions to send him to the police, and he would be released to the general public.

He did this about 10 times until police officers noticed him back on the streets. This stunt forced the state to change their procedure for detaining mentally unstable suspects.”

As someone who is pretty obsessed with crime, these stories were very interesting to me.

Now we want to hear from you!

Have you run across any wily criminals in your day?

Maybe as a cop, a lawyer, or in some other capacity?

Tell us about them in the comments!