Undercover operatives have one of the toughest jobs in law enforcement, and their activities can help bring down even the most bulletproof of criminal enterprises. Sometimes, however, as with all human endeavors, there are problems. The following operations were in the best of cases spectacularly ill-conceived and in the worst accomplished the exact opposite of their intended purpose. Some of the names of these operations were made up. Some, amazingly, were not.

10 Operation Wheelchair

Vancouver Police sergeant Mark Horsley had a simple but brilliant plan to put a dent in a gang of thieves that had been conducting a string of robberies on the east side of town in 2015. These cowardly bandits had been robbing disabled citizens in wheelchairs, and Horsley planned to catch them in the act by posing as a wheelchair-bound man himself. For five days, he tooled around the city’s most crime-ridden areas with money hanging out of an open fanny pack. The ploy attracted plenty of attention—just not the kind he had been expecting.

Despite over 300 contacts with citizens, nobody robbed him. They gave him money instead, although he was doing nothing resembling panhandling. Many people just stopped to chat and see if they could help, and two separate people brought him pizza. Only one man reached for Horsley’s fanny pack . . . to zip it shut for him and tell him that he should be more careful with his things. Horsley even recognized crooks he had busted in the past, approaching him to see if he needed assistance. It would appear that either the reports of roving bands of wheelchair robbers were highly overstated, or the Vancouver PD undercover unit has a serious leak.

9 Operation Have It Your Way

In 2016, Officer Nicole Fair had only joined the Thurmont, Maryland, police department about a month prior to her first big assignment. The tiny town of about 6,000 was having a bit of a problem with drugs, and citizens had reported dealing taking place out of the local Burger King. As Fair was not well-known in town yet, she was inserted into the fast food joint to go undercover as an employee and catch the dealers.

For two months, Fair flipped burgers—twice as long as she had actually worn a police uniform at that time—and befriended fellow workers. Finally, she hit pay dirt when she got employees Tommy Lee Miller and Jonathan Moser to sell her the goods. Speaking to the local paper, Fair said: “I was hired to help and protect the community of Thurmont, and that was what I was doing. You hear about all the drug problems [ . . . ] we’re really feeling the effects of it. To be able to do something to directly address that, especially being a new officer, was extremely rewarding.”

The drug haul? 5 grams of marijuana (roughly $50 worth) and two pills. Thurmont, you can sleep easy.

8 Operation Autistic Kid

Burger restaurants are one thing, but everyone agrees that drug dealing in schools is serious business. Since the 1970s, police have used youthful-looking cops to go undercover at high schools and ferret out the dealers, but one such operation at Chaparral High in Southern California in 2012 took a wrong turn on the first day. The undercover cop, “Dan” to his high school friends, immediately befriended young Jesse Snodgrass, an autistic student with bipolar disorder who had extreme difficulty keeping up with conversations.

“Dan” asked Jesse if he could score some weed, and Jesse said he could, barely cognizant of what that meant and ecstatic to have made a friend. After coming up with $20 worth of pot that he’d purchased from a guy outside a legal dispensary, Jesse was arrested and charged with drug dealing.

A judge, recognizing that there’s no way this crime would have ever taken place without the officer’s involvement, threw out the charges. A subsequent lawsuit filed by Jesse’s family against the school district was also, unfortunately, dismissed.

7 Operation Backfire

In 2012, a new store called Fearless Distributing opened in downtown Milwaukee. It was, to put it plainly, a front. Those staffing the store were agents of the Bureau of Alcohol, Tobacco, Firearms and Explosives (ATF), and they were determined to take some illegal guns off the streets by buying them from felons through their storefront. It didn’t work out quite how they intended, but perhaps you’re asking for problems when you name your sting Operation Backfire.

Pretty much everything that could go wrong did. For one, the sting failed to net a single gunrunning operation. Many arrests were made, but the ATF was found to have targeted mentally disabled people almost exclusively, and only a few low-level charges were filed. The store was broken into and robbed of $35,000 worth of merchandise. Agents caused $15,000 worth of damage to the property, resulting in a lawsuit by the landlord. Bungled handling of guns resulted in a military-style machine gun hitting the streets.

After the Milwaukee Journal Sentinel broke the story, they took a look at a few other ATF operations—and discovered that they had employed similar tactics, with about as much to show for it, in at least six storefront stings across the US.

6 Operation Helping Hand

From 2010 to 2012, Florida’s Tri-County Task Force, which strangely consisted of only two agencies, attempted to stem the flow of laundered money from the state’s drug trade by going undercover as money launderers. Operatives from the Bal Harbour Police Department and Glades County Sheriff’s Office would pass tips and information on to federal agencies, which would move in to make the bust when they had enough to do so. The operation was a success, resulting in the seizure of $30 million in dirty money.

Except that the $30 million wasn’t all of the money laundered by the undercover task force. In all, over $70 million was laundered for drug cartels by the task force, more than twice what was seized. The agents involved took a nominal fee for their services, skimming $2.4 million for themselves, which went to various operating expenses like stays at resort hotels and meals at expensive restaurants. After the Miami Herald exposed these shenanigans, the heads of the departments involved in the sting were terminated, and the operation itself was dismantled.

5 Operation Illegal Business

You may recall that in 2015, several states moved to defund Planned Parenthood after a series of undercover videos shot by the “Center for Medical Progress” (CMP) purported to show illegal activity within several of the clinic’s locations, including the sale of aborted fetuses. A grand jury was convened, and it was determined that multiple felony charges were in order—for the people who produced the videos.

The grand jury found that Planned Parenthood was not engaged in any kind of illegal activity and that the videos were edited deceptively to imply that the opposite was the case. Because of this, CMP founders David Daleiden and Sandra Merritt, the creators of the videos, were charged with felony counts of tampering with a governmental record. On top of that, Daleiden was charged with prohibition of the purchase and sale of human organs, because he offered—in a video that he shot—to buy human tissue, which is illegal. Although these charges were eventually dropped in July 2016, a lawsuit filed by Planned Parenthood against the pair is moving forward.

4 Project Gunrunner

In the mid-2000s, before they’d moved on to busting confused, mentally impaired people in Milwaukee and across the nation, the ATF was busy trying to keep guns from crossing the border into Mexico and getting into the hands of the drug cartels. The nationwide project, centered in Arizona and Texas, did indeed result in a good number of seizures, but the unfortunately named Project Gunrunner proved to be even better at doing what its name implied: running guns.

The project’s strategy was to facilitate “straw purchases” of firearms (which is the illegal purchase of legally obtained guns) and then trace their path into the depths of the cartel, exposing the supply chain. The second part didn’t work out so well, but the operation did result in about 2,500 fresh guns crossing the border and plopping into the cartels’ laps, as estimated by an actual ATF agent. Since the bungled operation has come under fire, it has even been suggested that the ATF was attempting to boost the number of US guns being supplied to the cartels to justify their budget or even for political reasons.

Amazingly, this was not the only time that this incredibly flawed strategy came back to bite the ATF.

3 Operation Fast And Furious

In 2009, an undercover operation began targeting several Phoenix residents thought to be moving guns. For years, undercover agents watched as guns flowed freely through safe houses, resisting every bit of their training to seize them as their superiors repeatedly told them to let the sales go through. By the end of what would become known as Operation Fast and Furious (because one of the suspects belonged to an underground car club) the ATF had let over 2,000 firearms cross into Mexico unimpeded.

The whole sorry saga of the “ATF Gunwalking Scandal” came to light after US Border Patrol agent Brian Terry was killed with a gun that the ATF had declined to remove from the streets. Many more firearms set free by the ATF have been found at crime scenes on both sides of the border. According to former Mexican attorney general Humberto Trevino, at least 150 Mexican civilians have been injured or killed as a result.

2 Operation What Private Property?

Early one morning in 2012, Craig Patty got the weirdest phone call of his life. The owner of a small North Texas trucking company with only two trucks, Patty found himself being informed by a business partner that one of his drivers, hired only five weeks before, had been shot dead inside one of the trucks, which had been loaded up with with enough marijuana to, well, fill a truck. Stunned, Patty tried to figure out how he could have fallen in with drug dealers—but he hadn’t. He had fallen in with an undercover DEA agent, who had been using the truck to try to bust smugglers.

The operation had gone spectacularly awry when said smugglers attempted to hijack the truck and its shipment, killing the undercover operative in a hail of bullets in full view of a dozen federal agents and local police. The officers involved, not all of whom knew each other, even ended up shooting at each other in the confusion, with one Houston cop wounding a sheriff’s deputy.

A lawsuit brought by Patty against the DEA for more than $1.3 million was dismissed in 2015, finding that the DEA was not even liable for his bullet-riddled truck. The decision is currently being appealed.

1 Operation Never Mind

In 2013, Worcester, Massachusetts, police were conducting an online sting operation aimed at snaring child predators. Posing as a 14-year-old girl, an undercover agent began a conversation with a user going by the name Latenightcop171. Soon after the user began making sex talk, officers discovered his identity: Neil Shea, an officer in their department.

So, did they reel him in? Not exactly. The undercover agent was told to terminate the conversation, ostensibly because “no line had been crossed” and there was “insufficient evidence to pursue a criminal complaint.” That is, despite this exchange:

Undercover — What can you teach me
Latenightcop171 — Lot of things
Latenightcop171 — We’d have sex

Also, after the conversation was terminated, Shea left a friend request for who he thought was his underage sexual prospect. While this may seem to indeed be sufficient evidence of the officer’s intent to pursue sex with a minor, the Worcester PD disagreed. Shea was allowed to resign and is free to collect his retirement benefits.

They walk among us! No, not aliens. Royals have a long and illustrious history of shrugging off their robes and crowns and getting stuck in with the general public. Sometimes, they did so because they had no choice or because they wanted to suss out what the “real” people thought of their rule. Other times, they just wanted to let loose and have a bit of fun.

Royalty today like the Dutch royal family live quite like the rest of us, and others like the British royals still live in castles. Find out how they used to rub shoulders with the great unwashed and why!

10 The French Royal Family

In the summer of 1791, the French royal family were forced to flee the revolt of the peasants and lower classes.^[1] They were aided by Swedish count Axel Fersen in planning their escape, disguising themselves as a group of German nobility. On June 21, 1791, Fersen came to the Tuileries disguised as a coachman to pick up the royal children and their governess, with Prince Louis dressed as a girl to further avoid suspicion. The king and the queen, Louis XVI and Marie Antoinette, left on foot separately and slipped away to meet Fersen later on. They were nearly caught by a night watchman as they left but managed to join their children and Fersen and take a coach to Varennes.

They might have made it and escaped the guillotine had they taken a faster coach, but Marie Antoinette insisted on a large, yellow coach that would be big enough to take the whole family. Traveling at only 11 kilometers per hour (7 mph) and experiencing a wreck on a bridge meant that they were severely delayed. A postmaster recognized the king and rode ahead of the party to Varennes, where they were arrested on their arrival.

9 Mary, Queen Of Scots

Mary was imprisoned at Loch Leven castle after being denounced as an adulteress and murderer and was forced to abdicate to her son.^[2] She had two escape attempts there, the second being considerably more successful than the first. She tried at first to flee as a washerwoman but was caught when the boatman saw her white hands under the rags. During this attempt, a set of keys to the castle were dropped in the lake and were not found again for 300 years.

She managed to escape on May 2, 1568, when her accomplices drugged half the island with wine and had “pegged” the boats to the shore, preventing them from following her. It was during the May Day festival when Mary walked out of the castle gates in full view. Her accomplice, a young boy called Willie Douglas who had dressed as the “Abbot of Unreason” for the festival, had dropped a handkerchief over the castle keys belonging to Sir William Douglas. Sir William noticed nothing, as he had indulged in a little too much wine at this point. Mary escaped that day but could not escape her fate, as she met the executioner at Fotheringhay Castle in 1586.

8 King Abdullah II Of Jordan

In 1999, King Abdullah of Jordan was reported to have gone undercover as a journalist, a practice his father had also often undertaken during his reign.^[3] On this occasion, his identity was revealed. The king had arrived in Zarqa with an accomplice, the head of the palace press center, who was masquerading as another journalist.

The king wanted to hear from businessmen and traders without fearing that they were not telling him the truth about the kingdom’s duty-free zone. The disguise was a shaggy white beard, a white robe, and a red headdress and held up only until the zone’s officials began asking for the TV crew’s license. The king had to unmask himself at that point but has continued to visit hospitals, border crossings, and public services to find out what people really think, without his royal status getting in the way.

7 Princess Elizabeth

On V.E. (Victory in Europe) Day, May 8, 1945, Princesses Elizabeth and Margaret were permitted by King George VI to leave Buckingham Palace and join in the celebrations when Nazi Germany surrendered to the Allied forces.^[4] Sixteen members of the royal household were to accompany them in the biggest party in history. They left from one of the palace’s back entrances and walked down the Mall with everybody cheering and shouting, this time to mark the end of war instead of at the sight of royalty.

Princess Elizabeth wore the uniform of the Auxiliary Territorial Service, as she had been serving with them during the war, but Princess Margaret did not disguise herself, instead wearing glamorous clothes befitting her royalty. Their cousin, Margaret Rhodes, remembers them all entering the famous Ritz Hotel and joining a conga line to many raised eyebrows from the older ladies there. The party didn’t return to the palace until 6:00 AM the next day. The queen remembers it as being “one of the most memorable nights of [her] life.”

6 King Charles II

In September 1651, Charles II had lost to Oliver Cromwell’s army, and a £1,000 reward was issued for Charles’s capture.^[5] Charles had to cross the country from Worcester to Shoreham on the coast and sail to France to escape the Roundheads, a feat he managed in a little over five weeks. The king was a tall man, over 183 centimeters (6′), with a dark complexion and a voice and manner that naturally made him stand out from a crowd.

Brothers George and Richard Pendrell helped the king to adopt a local accent and to walk like a laborer. Charles disguised himself as a manservant to a woman named Jane Lane, who had a pass permitting her to travel 161 kilometers (100 mi) to Bristol. He evaded capture so many times that the journey became known as the Royal Miracle. His trek included 965 kilometers (600 mi) of travel by any means necessary and can be followed today on the Monarch’s Way footpath. Afterward, from the safety of France, Charles spoke of his journey as one that allowed him to understand his subjects in a way no other king possibly could.

5 Roman Emperor Nero

Nero, who was not much more than a teenager when he became emperor of Rome, would put on a cap or wig and gallivant around the city with his friends.^[6] Sometimes, they just played pranks on people, but oftentimes, they would beat and accost men in the streets, stabbing those who resisted them and throwing them into the sewers. Nero would break into and steal from shops and sell his loot at the market in the palace, divide the proceeds among his group, take his earnings, and carry on carousing.

Nero caused so much trouble that he nearly lost his eyes on one occasion, and he was almost beaten to death by a man of the Senate whose wife Nero had maltreated. After this, Nero would travel with tribunes behind him at a distance, ready to intervene at any sign of trouble.

4 King Charles XI Of Sweden

Charles XI (reigned 1660–1697) is said to have traveled throughout the land wearing a grey cloak to conceal his royal uniform in order to speak with local officials, who he would test for corruption, and to local people, who could reveal any perceived oppression to him.^[7]

The king may have taken inspiration for this disguise from the Old Norse legend of Odin, who would speak to mortals in disguise in a similar fashion. Charles’s disguise became legendary, and he came to be referred to as the Greycoat (or Grakappan).

3 King Matthias Corvinus Of Hungary

King Matthias Corvinus was crowned in 1464 and was a very popular ruler.^[8] His justice reformations and advocacy of talented people regardless of social standing made him a celebrated ruler of the people. He was a patron of science and art with a good military career, and although taxes had to be raised in lieu of being at war (mainly with Turkey), he remained well-liked.

One legend of King Matthias concerns a disguised visit to one of the Turkish camps. Dressed as a food seller, he remained all day outside the Turkish general’s tent. The next day, he sent a message to the general, describing his camp and the food that was to be found there as proof. Completely unnerved that the king had been in the camp, the general fled right away back to Turkey.

On another occasion, at the Siege of Shabacz, Matthias, disguised as a soldier, rowed with one other soldier along the fortress to discover where best to launch an assault. The Turks opened fire, and his companion was killed, but the king calmly continued to search the walls for the best point of attack.

2 Sultan Alauddin Riayat Shah Of Malacca

Malacca is a state in Malaysia that was ruled by Sultan Alauddin from 1477 to 1488.^[9] He regularly checked on his people’s opinion toward his ruling decisions by walking among them in disguise and is said to have been a fair and good sultan. He would walk about at night to reduce the chances of being discovered, and on one occasion, he came upon a thief and ran after him, feeling appalled that this should happen in his kingdom.

Alauddin ultimately died under mysterious circumstances, and his family members were fighting each other for supremacy even in his lifetime. His two wives were fighting as to which child should become heir after his death, his brother was envious of his position on the throne, and his court was full of possible enemies from surrounding Malaysian nobles.

1 Princess Diana

Comedian Cleo Rocos wrote an account of when Princess Diana went to a London pub with her and Freddie Mercury in her book The Power of Positive Drinking, published in 2013.^[10] In the late 1980s, Princess Diana, Freddie Mercury, and Rocos went for a night out in South London at the Royal Vauxhall Tavern.

They gave Diana a disguise of an army jacket, sunglasses, and a cap. She was mistaken for a gay young man, and nobody recognized her, so much so that she was the only one out of her famous group to be able to order their drinks at the bar unmolested by the crowd in the pub.

Alexa is a psychology, sociology, and anthropology researcher in Ireland.