Bizarre Cases of Prison Smuggling

From cockroach cigarette deliveries, to fake feet felonies, suitcase scandals, and a whole lot more equally insane contraband mayhem, let’s open the cell door on the most bizarre cases of prison smuggling the world’s ever known!

Phones Hidden In Shoes

What's the most important thing you should do before you go to prison? Get yourself a fresh pair of kicks. You never know the next chance you’ll get. Well, one Oklahoma inmate was recently denied some fresh penitentiary drip for a truly shocking reason.

Officers discovered concealed in the box of a new pair of all-black Air Force 1s were 6 tiny cell phones. Mistake number one, everyone knows all-black forces are reserved for crimes. The phones are so tiny you could easily mistake them for toys but they’re fully working! And they’re a lot easier to stash inside the cell than an iPhone Pro Max.

On a similar vein, one prisoner had theirs confiscated after officers discovered they were using it to smuggle in cell phones. Life’s going to be hard inside without your prosthetic but that’s what you get for having a close brush with the law.

Smuggling Steroids

Ever wondered why so many prisoners look so jacked? Surely that’s not just doing push-ups in their cell, right? Well, if they were incarcerated with one Ashley Keany, maybe not. Keany had forged a secret relationship with an operations instructor, Sally McGrath at Garth Prison in Lancashire, England. But as well as giving Keany the goods, McGrath was also bringing actual goods into the prison.

After she was caught sneaking pouches of tobacco on her person, police raided her apartment and found packages of Testosterone propionate, an anabolic steroid used for accelerating muscle building. They also found mobile phones exposing her secret rendezvous with Keany with evidence of her being paid to be a part of his smuggling ring.

Do you know what else is powerful? Money. That’s how ex-Royal Marine Matthew Taylor found himself on the wrong side of the law. He was working as a supervisor at HMP Oakwood, near Wolverhampton, England when he met career criminal Mark Clarke. Taylor was convinced to work with Mark’s partner, Donna Duffus, to bring steroids into the prison.

The plan never materialized because Taylor got cold feet and suddenly demanded more money. But by now it was too late. His phone records had been tapped and the evidence against him was irrefutable. Taylor was jailed for one year and nine months.

Macomb County Rap Video

You might think prisoners getting their hands on phones is only to serve their nefarious wrongdoings but that’s where you’d be wrongdoing. Two Detroit inmates at Macomb Correctional Facility managed to expose mistreatment in the Michigan prison system with the use of a smuggled phone. The cellmates, who go by 24 Superbadd37 and 82 Treezy Banger, self-shot a music video for their song IN DIS CELL from their cell. Check it out in the footage below:

IN DIS CELL by WavHouse

Through their song, they highlight the bad conditions inside Macomb. There’s water flooding across the floor and Treezy Banger has to use his blanket as a flood buffer to stop it coming in. You shouldn't feel too sorry for them though, they are in there for second-degree homicide and armed robbery. As a result of their stunt, the two felons were separated awaiting further criminal charges.

Baked Goods Smuggling

For centuries crafty crooks have been using sugary cakes and other baked goods as facilitators for crimes. Back in the early 18th century, notorious criminal pickpocket William Blewitt, blew it getting caught stealing and wound up imprisoned on a ship ready to deport him to the Caribbean. While on board he learnt of a conspiracy by the other prisoners.

They’d managed to smuggle a collection of files and saws onboard, hidden inside gingerbread cakes, and were intending on using them to escape before the ship set sail. Well, Blewitt saw an opportunity to gain favor, so the wily thief snitched on his fellow prisoners. And sure enough, he was rewarded by the captain with his freedom.

Some hundred years later another prisoner, John C Wilderman, was locked up in Middlesex County, New Jersey for stealing a mile of trolley wire and causing a cable car to get stranded. John’s wife was a tremendous baker. She’d bring her husband mince pies every week, and as the smell wafted through the jail, the warden would always get jealous. So, one time she visited, Mrs. Wilderman brought the warden his own special pie, which he immediately devoured before sinking into a deep sleep.

Upon awakening, he found John’s cell empty except for two discarded hand saws. Whether the saws were hidden in John Wilderman’s pies, Mrs. Wilderman smuggled them in by some other means, or the cunning wife slipped the warden a little sleepy time juice, we’ll never know.

Over in Los Angeles around the same time, a Mr F.J. Humely was sent down for passing a forged check. While inside, he was sent a package containing two elaborate and delicious-looking cakes. Only, the Sheriff who intercepted the package thought the cakes felt unusually heavy.

So, he plunged his hands into them and sure enough, found half of a 38-caliber revolver in each. Apparently, Humely’s plan was to assemble the revolver in his cell and use it to threaten the guards but it backfired without a single pull of the trigger. Humely was sent down for seven years.

In 2019, guards at HMP Stafford in the UK were alerted to a major security breach. Rumour had it one of the prisoners was concealing a dangerous weapon in their room. So, the guards conducted a full search of the cells, and found some loose electrical casing in one of them. After looking inside, they uncovered a lump of stale bread shaped like a gun.

According to the guards, from a distance, it did actually look real. It’d been painted black and laboriously carved into shape. Plus, it’s only got to look real enough to facilitate an escape attempt. Who’s going to feel bold enough to test their luck and get close enough to find out?

But what’s scarier than a fake bread gun? A real one, hidden in bread. That one didn’t quite make its way past the prison gates it was an attempt to smuggle firearms past a security checkpoint in Nigeria. But the crimes responsible were arrested and almost certainly did make it past the gates.

Florida Man Arrested For Breaking Into Jail

Having friends or family locked up knowing you can’t see them must weigh heavy. Well, it did for 24 year old Patrick Rempe. His buddies were all serving time inside Indian River County Jail in Florida, leaving Patrick on the outside by himself. He’d tried to keep himself entertained, but nothing felt the same without the homies with him.

But one night, heavily influenced by something he shouldn’t have been smoking, Patrick conceived a crazy plan. If he snuck himself into jail he could hang out with the boys again, and then leave before the guards ever found out. What could go wrong, right?

Turns out, everything. Patrick was off his face. He crashed his car directly into the jail and then got stuck climbing the barbed wire fence. But that wasn’t the end of his problems. Rempe was charged with aggravated assault on a law enforcement officer, battery on a law enforcement officer, three counts of felony criminal mischief, leaving the scene of a crash, $5,000 of property damage, and driving under the influence.

Inmate Caught Smuggling Home-Cooked Food

Nothing beats a homecooked meal. Many would do unspeakable things for the sweet taste of mommy’s Gumbo. And that’s about the only thing we have in common with 25 year old narcotics offender, Joshua Hansen. Officers at Jefferson County Sheriff’s Office had received a tip-off that prisoners were escaping from federal prison in Beaumont, Texas, to a special drop zone before coming back with various contraband. So, prison staff set up surveillance, and sure enough they saw a vehicle drop off a duffel bag at the expected location before pulling off again.

About 2 hours later, Joshua Hansen was spotted running off prison grounds, grabbing the bag, and sprinting back. Officers intercepted him and confiscated the bag. But when they prised it open, what they found wasn’t what they’d expected. Three bottles of brandy, a bottle of whisky, packaged snacks, fruit, candy, tobacco, and a huge amount of home cooked food like sausages, chicken, rice, and green beans.

Cat Caught Smuggling Mobile Phones

Guards at the penitentiary in Russia’s Komi Republic caught a four-legged furry felon climbing the fence of Penal Colony No.1 with two packages strapped to its back containing cell phones and chargers. Believe it or not, although that was the first cat smuggler in Komi, it was far from it in Russia as a whole. Cats are trained by criminals and used extensively throughout the prison system to get things both in and out.

In 2012, narcotics police caught a cat smuggling all sorts of horrific contraband. The cat, presumably a prison pet, had been smuggled out of the prison by released inmates who handed it over to local dealers. The dealers stuffed its collar with illicit goods before releasing it to make its way back to the prison.

And those cat burglars aren’t just in operation in Russia. In Sri Lanka in 2020, a cat used to mule narcotics and SIM cards to prisoners was detained in Welikada prison. Not only did they put Tiddles in the slammer, but when guards went in to feed the feline fugitive, it dashed straight past them and out of the door.

Stuffed Burrito

Mexican food is so good it can turn a straight shooter, like Sheriff’s Deputy Henry Marin, into a crooked man. In 2012, he was caught in an elaborate sting operation trying to smuggle a delicious bean and cheese burrito into a courthouse jail. The plan was cooked up by Carlos Gallardo, a shotcaller for the Mexican Mafia,.

An unnamed woman would arrive at the jail with the goods in hand. She would hand the burrito to Deputy Marin, the inside man who could bypass the jail’s tight security. Marin would smuggle the burrito to another prisoner, Robert Alavez, who would then be in charge of delivering the burrito to Carlos Gallardo. What could go wrong?

Well, Gallardo’s phone conversations with the unnamed woman were tapped by prison officials. Even though Gallardo spoke in code, the guards knew he was up to no good. So they reached out to the woman, who broke down and switched allegiances, and the double cross was in action.

When she arrived at the courthouse that day she was followed by two plain-clothed officers who set everything up. She waited for Marin to poke his head out of the courthouse, made the drop-off in secret, and alerted the officers in tow. They leaped into action, arresting Marin and busting the plan.

Cockroach Trained To Carry Cigarettes

Prison sure sounds tough but solitary confinement sounds a whole lot worse. In Amarillo, Texas, in 1938, one crafty prisoner found a way to make things a little easier for him and his fellow inmates though and that was cigarettes. However, smoking cigarettes was banned for prisoners in solitary confinement.

So, how’d they possibly get their hands on them? That was the question on the County Jailer’s lips. Perhaps one of the prisoners had a key? But if that was the case, why wouldn’t they just escape? Then one day, while the jailer was searching one of the cells, his colleague spotted something incredible. Walking across the corridor was a large cockroach with a cigarette strapped to its back, heading towards a crack beneath the cell door.

After the jailer noticed, it wasn’t long until prisoners in the non-solitary cells told him what’d been happening. Apparently, the roach had been trained to respond to a whistle. First, a prisoner outside of solitary would tie a cigarette and match to its back, then somebody in solitary would whistle, and it would dash the banned goods to them.

As unbelievable as the story sounded, the jailer decided to test the theory. He placed the roach with the cigarette attached in another room, and whistled. Amazingly, it made its way back to him. And after several more tries, it came every time.

But the mystery is not yet solved, scientists have been able to train cockroaches to perform menial tasks by manipulating light or temperature conditions. But that’s in a controlled lab in the 21st century not in a dingy solitary confinement cell in the 1930s. No one’s been able to replicate any test in controlled conditions since. Yet, at least two separate newspapers did report on the incident in 1938.

Hole In The Wall

If you believed everything you see in the movies, you’d probably think prisoners shimmy contraband up and down a haphazard daisy chain of bedsheets. But that happened in actuality! Yes, prisoners in Oklahoma County Detention Center were caught pulling a Shawshank Redemption to smuggle goods in and out of their 10th-floor cell.

Using makeshift tools, they’d carved a hole into the external wall above the employee parking lot. They’d been using it to lower their makeshift rope down to the ground, where accomplices would attach the banned goods. Then they’d haul back up the wall.

Except it wasn’t the smartest of plans. During one haul in 2021 a detention center officer was taking his break in the courtyard and somehow happened to notice the box of goodies being heaved up right in front of him. Upon raiding the cell, staff uncovered 23 cell phones, a pound of tobacco, half a pound of Satan’s broccoli, and a whole bunch of other prohibited items.

Inmates drill hole in wall at Oklahoma County Jail in smuggling scheme, authorities say by KOCO 5 News

However, according to a jail spokesperson, that is always going to be a problem. The jail was built giving prisoners immediate access to the outside through just a few feet of concrete. There’s always gonna be some crafty crook trying to do something they shouldn’t. Maybe next time they should have strapped the contraband onto a crossbow arrow and fired it over the fence instead. That’s what that confiscated crossbow and arrows was used for when it was found.

Stuffed Rear

Sometimes the best way in is through the back door. And, yes, that means exactly what you think. On February 11th, 2011, at Sarasota County Jail, Deputy Makowiecki was conducting a routine search of the inmates in cellblock 204WW.

However, he noticed something shifty about prisoner Neil Lansing. Makowiecki ordered a strip search where they discovered Lansing had over thirty items hidden in nature’s back pocket. There were 17 pills, one cigarette, 6 matches, a flint, an empty syringe, a ChapStick container, a CVS receipt, and a coupon.

Okay, there are a few things to dig into there. Six matches and a flint for one cigarette?! Secondly, the CVS receipt is crazy. What’s he hoping to do, return some of those items once he’s released? You'd doubt he’s getting out within the 30-day returns policy and even if he did go free, there are more than minor signs of wear.

The old exit hole trick is shockingly common though in released X-ray scans, prison guards have shown loads of convicts conceal phones up there. That's probably why they call it a butt dial, you’d need nerves of steel to walk through security with a phone stashed in the chute. One surprise sneeze and it’s game over.

Bible Hiding Phones

Inmates at the New Bilibid Prison in Manilla, The Philippines, had their bibles confiscated for taking the good Lord’s words out of context, quite literally. Prisoners had cut pages out of their bibles to stash cell phones, chargers, signal boosters, and other computer parts. And here’s another example where a prisoner has used a hymn book to conceal their phone. No one suspects the person with a bible under their arm other than God of course. It's unsure he’d approve of any of that.

Smuggler Birds

You know that old saying - birds of a feather flock together. Well, that’s true for prisoners and even truer for the ones using real birds to ferry their ill-gotten gains. Prison guards in Franco da Rocha, Brazil became suspicious when they spotted inmates frantically chasing a bird in a suspicious vest. Unfortunately for the prisoners, the guards managed to catch the bird first and discovered a secret cell phone and battery strapped to its back. And that’s one of the more innocent ones.

In 2015, another bird wearing a backpack containing 28 grams of naughty stuff was spotted outside La Reforma prison, in San Rafael de Alajuela, Costa Rica, and apprehended. And over in Kuwait, guards nabbed a homing pigeon ferrying a whopping 178 pills to its destination.

The really wild thing about that is, homing pigeons only work by flying back to where they’ve been trained is home they can’t just fly to any old destination. So, someone on the inside of those prisons must’ve spent months training the pigeons undetected, then sent them off to collect their packages and return “home” with them.

Drones

Birds, they’re a little old-fashioned. One gang in Birmingham, England, used far more modern tech to control the skies. Inmate Lee Anslow was incarcerated at HMP Hewell in Redditch, yet he was still able to orchestrate a complex series of drops from behind bars all using drones.

In around a year, Anslow made a minimum of 55 drops to prisons across the country, providing inmates with phones, SIM cards, and memory sticks along with other illicit goods. But how when he was stuck in prison himself? Well, he didn’t do it alone. He’d communicate with drone pilots on the outside using an illegal phone. They’d then get in touch with prisoners on the inside, who’d use their own secret cell phones to guide the drone pilots to drop zones before unhooking the bagged goods with a stick.

But the whole empire collapsed after Police intercepted eleven drones that either crashed or were recovered loaded with contraband. All the evidence pointed back to Anslow, and when they raided his cell they found $25,000 worth of contraband, cell phones, earphones, and a list of contacts. And in the bottom of a Nesquik tub, there was a set of scales.

Strippers Posing As Paralegals

Prison can be lonely. But back in 2011, some prisoners at a maximum-security facility in Miami found a way to get themselves a little extra loving. Attorneys visiting high-profile clients at Miami’s Federal Detention Center were accompanied by some rather alluring paralegal aids. We know better than to objectify women in the workplace. But those paralegals were more like para-illegals.

When a guard was checking out the “discovery room” where attorneys and prisoners could discuss elements of their trial, they burst in on one of the legal assistants and a prisoner! And that’s not all. CCTV footage captured another paralegal giving a prisoner a little private dance.

Other times they fed prisoners alcohol by slipping straws through the grates, snuck them money, and even brought in naughty magazines. So, how the heck was all that being allowed to happen? Essentially, all attorneys need to do to designate a legal assistant is sign a form.

So, at the behest of their criminal clients, they’d been choosing rather untraditional aids. Ones that normally wouldn’t be allowed near a maximum-security facility. But thanks to being classed as legal assistants, the fake aids could walk straight in, along with any contraband they felt like it’s one of the boldest smuggling swindles imaginable! And it’s super difficult to prove, so the scam has been allowed to continue.

Okay, you can sneak someone into prison, but what about sneaking someone out? When Antonieta Robles Saouda visited her lover Ibrain at Jose Antonio Anzoategui, prison officers were suspicious because she’d taken a large, pink suitcase in with her. Weirder still was watching her struggle to carry it out again. The guards found Ibrain squished inside the case! He was promptly escorted back to his cell and Antonia was arrested.

If you were amazed at these bizarre cases of prison smuggling you might want to read about why prisons ban everyday items. Thanks for reading!