Sometimes, going in disguise is a smart way to bring down the toughest bad guys (like the guys who perpetrated these 8 Awesome Robberies With Even More Amazing Getaways). It’s the cool life, hanging out with the seediest of society’s underbelly, knowing that at any minute your cover could be blown. You’ve got to watch your every move and keep your eye on the bust.
Going undercover is awesome, unless you’re an idiot. Then you make this list, which is for people who totally botched undercover operations. They completely blew them. They would have had a better chance donning a clown wig and saying, “Hi, my name’s Bozo, and I’d love to join your motorcycle gang! Got any meth for sale?” Check out these 15 Worst Attempts At Going Undercover. These 10 Coolest TV Cops would never be caught dead in a tu-tu.
15. Operation Speakeasy
So, you’re in the F.B.I., but you always dreamed of owning your own bar. Awesome, why not act like these guys, and do it all on taxpayer money? The premise was to create a bar that would become a hip hangout for mafia gangsters.
It gets worse. For some unbelievably predictable reason, G-men suck at running a bar, much less one with a “secret theme.” So they hired an outside consultant to join in on the partnership. After a year, the bar wasn’t attracting mafia clients, in fact it wasn’t attracting any clients. So the F.B.I. canceled the operation and left, leaving the outside consultant in debt for over $100,000.
14. DEA Plants Coke On Plane, Forgets To Tell Customs
Suspected drug lords were waiting in Miami for a plane from Belize, that was supposed to be loaded with cocaine. Hoping to trap them, the D.E.A. covertly placed 45 kilos of snowflakes on board the plane, expecting to nab the dealers in Miami.
However, things took a turn for the worse when the plane made an unexpected detour into Honduras. Unassuming passengers were roughed up by customs officials, who sure as Hell weren’t going to tolerate people bringing cocaine through South America. The D.E.A. was ordered to pay $1 million in damages.
13. Cops Try To Start Riot
Here’s a pretty hilarious video of cops caught in the act. During a protest. Canadian police show up dressed as masked protesters, attempting to incite riots by wielding rocks. When demonstrators, themselves, ask the undercover police to put down the rocks and they refuse, everyone flips out and call them narcs.
12. Jenna Bush Caught Using Fake I.D.
It doesn’t get much more depressing than this. You’re the daughter of the most powerful man in the free world, and your best ruse to get alcohol is a fake I.D? You couldn’t kidnap a foreign dignitary, holding him hostage for a four-pack of wine coolers?
11. Operation Corkscrew
Another colossal screw-up by the effa bee eye. Hoping to crack down on a growing problem of judges being bribed, the F.B.I. posed as car thieves. After bribing a judge to hook them up with other judges, the undercover agents start a huge network of bribery. Only, nearly all of the men that were “judges” weren’t really judges, or even involved with the judicial system. In fact, the man who hooked them up with these supposed “judges” was pocketing most of the cash, anyway.
10. Police Woman Dates Lonely Man For Half A Year
Hoping to lure a reclusive man into a murder confession, a police woman pretended to have a romantic relationship with him for seven whole months. During this time, she learned that he had never been intimate with another human being.
Now, it’s okay to sexually toy with a murderer for a long time, but it turns out he wasn’t even the murderer. The operation failed to net any charges, even when the police officer offered him sex in exchange for a confession.
9. British Police Lose Data Stick
The MI6 agency is the U.K.’s non-wacky version of the F.B.I. One thing they forgot to take seriously was a 2006 multi-million dollar undercover drug operation. The operation involved many agents taking on roles as covert operatives with secret identities. It worked great, until one operative left a memory stick on a train containing the names and secret identities of the whole party. The entire operation had to be scrapped.
8. I.R.S. Goes Undercover… Badly
In 1984, the Internal Revenue Service wanted a way to catch tax evaders and implicate the mafia in illegal betting. So they opened a fake bookmaking service that took real bets. The only problem? Real bookies are freaking hardcore. I.R.S. accountants are not. Real bookies collect their debts with threats of illegal force. Unable to break anyone’s legs, the I.R.S. began hemorrhaging money as no one would pay when they lost a bet. By the time the operation was canceled, over half a million dollars had been squandered.
7. Principal Arranges Illegal Sting
Finally fed up with the marijuana epidemic plaguing his otherwise-upstanding school, the principal of Porter Middle School in California decided to take matters into his own hands. The operation went remarkably smoothly. The principal asked a 12-year-old to buy some pot from a dealer, the deal went down, the principal called the police. Police were quick to step to the scene, as it is a felony to ask a minor to buy drugs. But at least the obviously-bored principal got to live the exciting life of a pre-teen drug-buster.
6. Cop Posing As Crackhead Wouldn’t Take A Hit
This bust seemed pretty simple. Cop poses as crackhead, buys some crack, profits. But the crack dealers suspected something was going down, and locked the undercover cop in the crack house. The deal was simple, take a hit of rock and they wouldn’t shoot him. Keep in mind, according to police law, he is legally allowed to hit crack if a gun is pointed at his head. Instead, the officer alerted backup, who raided the house.
5. C.I.A. Plane Crash Blows Open Iran-Contra Affair
In 1986, somebody (but not Ronald Reagan) was authorizing the sale of arms in exchange for hostages, covertly of course. The “covertness” was blown up when a C.I.A. plane was shot down in Honduras, and it’s previously-undercover passengers revealed themselves to be C.I.A. agents. Way to go, somebody (who is totally not Ronald Reagan).
4. The Matrix-Churchill Affair
Matrix-Churchill masqueraded as a wee machine tool company in the green hills of Coventry, England. However, the ish hit the fan when it was revealed in 1991 that the company was not only owned by Iraq, but had been creating tool machines that doubled as producers of weapons parts. Then, when the good citizens of England tried to bust Matrix-Churchill, the whole thing fell apart when it was revealed that the British government was in on the plans.
3. Officer Dresses In Drag
The Florida officers’ trick of dressing up to trick speeders had been working great. Over the past few months the officers had dressed as a repair worker, a homeless man, and a construction worker, while netting a huge number of speeders. However, one officer made the horrible choice of dressing up as a drag queen on a slow news day.
2. Police Officer Too Big of A Method Actor
Here’s another simple sting gone so so wrong by inept undercover operators. The sting was set up to bust prostitutes for prostituting. However, one cop decided he didn’t have enough “physical evidence” and began having a lot of sex with the prostitutes he was supposed to bust. Odd, he must not have known about the plentiful variety of prostitutes available on social networking sites.
1. It’s Miley With A Wig
The plot to the hit Disney show, “Hannah Montana” involves Miley Cyrus dressing in costume to lead a secret life as a regular schoolgirl. Hoping to recreate the experience, Miley planned a real-life foray while wearing a “normal person” disguise. However, this undercover operation backfired before it even began. Deciding her “normal person” wig was far too ugly, Miley took a curling iron to it, setting her hair on fire. Miley then stupidly concluded, “It doesn’t work in real life.”
For more failed detective work, watch as this car is stolen during a police interview. Or check out the 7 Most Inept Police Officers on Television. Our favorite, however, is still the guy who Calls 911 When Burger King runs out of lemonade.
Evan Hoovler co-wrote the National Lampoon book “Pimp It Yourself.” He is executive producer of the sketch comedy troupe Drunk Nerds.
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