The 6 Most Hilarious Undercover Operations Ever Pulled Off

#3.
Whack Dalia

The Case:

For a lot of newlyweds, after the honeymoon is over, the sex loses its allure and you suddenly realize the guy you're sleeping next to farts a lot and sometimes wears yesterday's underwear backwards, marriage gets to be a bit of a drag. You might say it can be murder. Pun absolutely intended!

At least, that's how things were for Dalia Dippolito, who, after marrying her husband Michael, suddenly realized that her new alliterative name made her sound like a character from a comic book, and decided to rectify the situation by taking her husband out old-school.

Taking a few lessons from the Rocky and Bullwinkle school of villainy, Dalia tried poisoning her husband a few times and even tried to frame him as a drug dealer. After failing so many times to inflict harm on him that shot right past the role of femme fatale into the realm of the tragically incompetent, Dalia's final master plan was to hire a hitman to do the job she couldn't.

The Stupidity:

About 30 seconds of research on the Internet would have taught Dalia the valuable lesson that hitmen are always undercover cops. Sure, there are probably real assassins out there under the employ of the Mafia and Apple, but the idea that a regular private citizen can just call up a gun for hire and draw up a contract kill is a classic example of the "real life is not movies" fallacy.

The worst part, for Dalia, is that the officer who posed as her assassin spent the entire negotiation trying to talk her out of it, doing the undercover police version of the "wink wink, nudge nudge" routine, informing her that a shitload of hard questions were going to come her way and she probably wouldn't be able to take the heat. We imagine that if he'd "accidentally" dropped his badge right in front of her, she probably still wouldn't have caught on.

Dalia assured him that she wanted the job done, and that she was "like, five thousand percent sure" of it. Cracked's Certainty Department has determined that Like Five Thousand Percent is as sure of anything that anyone can be, ever.

After Dalia hired the hitman, the police faked Michael's death, and Dalia completely bought it, doing her best to sell the performance of the distraught widow. Even after the police showed her that her husband was alive and well, and that the guy she'd tried to hire was a police officer, and that everything they had discussed had been recorded and videotaped, she still somehow figured she'd get away with it. After being hauled away to prison, she called her husband to assure him she was innocent, even though the only plausible denial at this point would be through some kind of alien conspiracy.


"This sucks so hard, def gonna be today's Facebook status, I'm so bummed."

#2.
Neo-Nazis Just Don't Try Very Hard

The Case:

The Neo-Nazis need all the good press they can get. Championing the works and deeds of the only man in history to completely destroy a particular style of facial hair for everyone until the end of time, they aren't exactly the most popular kids on the block.


"If you don't look like this, get out of my face."

So, when they were approached by Ron Furey, an individual who claimed to be an Australian journalist for the white supremacist publication The Right Way, they jumped at the chance to tell the world that, aside from Edward Norton occasionally face-stomping some dudes into a curb, they weren't all that bad.

The "journalist" would go on to meet several high-ranking Neo-Nazis who embraced this new member with great enthusiasm. Furey maintained these relationships for months, enjoying such pleasurable experiences as a white supremacist movie night, which involves masturbating to films about Hitler and rape. Furey often felt mighty uncomfortable during these festivities, and we can't really blame him, because...

The Stupidity:

...he's Jewish. And we're not talking "my dad is Jewish so I get gifts for Hanukkah and Christmas" Jewish, we're talking "my parents survived the Holocaust and I used to be an Israeli police officer" Jewish.

His real name is Yaron Svoray, and in the early 90s he agreed to go undercover to help the Simon Wiesenthal Center acquire a lot of firsthand information about the Neo-Nazi movement. This assignment was more difficult than shaving his head, practicing his cold beady-eyed glare and making sure never to shout "oy vey" when startled; the success of his infiltration relied upon the group he was investigating being unable to do even the most rudimentary of homework assignments.


Luckily, Nazis are dumb.

The Neo-Nazi magazine that Svoray claimed to write for didn't actually exist, had never existed and although he had a bunch of fake stationery mocked up to give the illusion of legitimacy, his cover would presumably be blown the moment anyone thought to type the words into Google (or, since this is the 90s, AltaVista). Honestly, guys. Would Hitler have approved of this kind of sloppiness?

#1.
Kindergarten Cop

The Case:

The Triads, or the Chinese Mafia, is such a problem in Hong Kong that the police force has a division which exists specifically to take them down. Not that they have much to worry about though, seeing as the crimes associated with the Triads appear to revolve around counterfeiting 50c pieces and petty copyright violations. Hey, it's a different culture.


Nerd crime!

Like any major gang, the Triads are always looking to recruit young members, and recently, this practice caused some serious problems for them. By identifying Triads who were attempting to lure students into their way of life, an anonymous undercover cop helped the Hong Kong police arrest a whopping 117 individuals.

How did he do it, you ask? Hilariously, we answer.

The Stupidity:

The cop posed as a 15-year-old boy.


Please tell us he dressed like this. Please.

As a young officer, he was able to successfully infiltrate the gang by pretending to be a high school student for several months. He befriended several Triads and witnessed a variety of criminal activities around the school. And the best part? He got the idea from a movie.


This movie.

Fight Back to School is not a realistic portrayal of undercover life. It's not even a badass kung-fu movie. It is a Hong Kong comedy movie about a cop who disguises himself as a high school student, gets made fun of and falls for the guidance counselor. That's right, the Asian version of Never Been Kissed brought down over a hundred members of one of the world's most elite criminal organizations.

Do you have an idea in mind that would make a great article? Then sign up for our writers workshop! Know way too much about a random topic? Create a topic page and you could be on the front page of Cracked.com tomorrow!

For more unfortunate criminals, check out The 7 Most Baffling Criminal Defenses (That Sort of Worked). Or compare these guys to the Hollywood versions, in 6 Baffling Mistakes Every Movie Criminal Makes.

And stop by our Top Picks (Updated 06.07.10) to meet the intern that brought down the nefarious Cracked neutical cartel.

And don't forget to follow us on Facebook and Twitter to get dick jokes sent straight to your news feed.

Recommended For Your Pleasure

To turn on reply notifications, click here

349 Comments

The Cracked Podcast

Choosing to "Like" Cracked has no side effects, so what's the worst that could happen?

The Weekly Hit List

Sit back... Relax... We'll do all the work.
Get a weekly update on the best at Cracked. Subscribe now!