The 6 Most Hilarious Undercover Operations Ever Pulled Off


When you watched The Departed, you might have had a difficult time suspending your disbelief that Leonardo DiCaprio was capable of stealing a pack of Juicy Fruit, let alone becoming a trusted comrade of lifelong gangsters. Surely, real criminals just aren't that stupid.


The FBI Pulls a Reverse Scarface

The 6 Most Hilarious Undercover Operations Ever Pulled Off

The Case:

The Gambino crime family is a Mafia legend. As one of the notorious "Five Families," the organization has been a major criminal empire since 1957, and as a result, they've been a high priority FBI target for decades. In 2002, the Bureau took a major leap forward when they got one of their own to successfully go undercover among the Gambinos.

Posing as Jack Falcone, a 390-pound jewel thief with a shining personality, a love of great food, a collection of expensive suits and an obligatory diamond pinky-ring, the agent fit right in among a bunch of hardened Italian mobsters.

The 6 Most Hilarious Undercover Operations Ever Pulled Off

"Say, that Snooki is a one spicy meat-a-ball. Amiright, my fellow pisans?"

The primary target of the operation was Greg DePalma, an aging family capo so terrifyingly batshit that he once took "a power tool to someone's head" because he suspected that the guy might be stealing from him. This did not deter Jack, who probably gets 90 percent of his 390 pounds from lugging around an utterly titanic set of balls.

Armed with a blank check from the FBI, Jack lavished DePalma with expensive gifts, from bootleg cigarettes to iPods, most of which were packed full of satellite tracing technology. The appeal to his apparent love of Apple products made DePalma swoon for his new best friend, to the point that he suggested making a "made man" out of the guy.

The 6 Most Hilarious Undercover Operations Ever Pulled Off

Becoming a made man is the Mafia's highest honor, reserved for its most trusted and loyal members. Due to the exclusive nature of the mob, it is almost always reserved for those who are of total Italian descent, although some exceptions are made for those who are half Italian. That's awesome, considering...

The Stupidity:

Jack Falcone's actual name is Joaquin "Jack" Garcia, and he was approximately as Italian as Zinedine Zidane.

In order to infiltrate the Mafia, the Cuban Jack Garcia had to literally adopt a new racial profile, and pull off the act in a room full of dudes who can supposedly guess what part of Italy you come from by smelling your marinara sauce from one hundred yards while blindfolded. How did he attain such an astounding mastery of Italian-American culture? Among other things, by watching hours upon hours of cooking shows.

The 6 Most Hilarious Undercover Operations Ever Pulled Off

The charade worked like a charm. From 2002 to 2005, Garcia successfully fooled every single Mafioso he came into contact with. Even when his cover was eventually blown, it wasn't because he was trying to pull a racial switcheroo that caused Al Pacino to talk like he had an overactive, and anti-Semitic salivary gland.

The 6 Most Hilarious Undercover Operations Ever Pulled Off

Pacino in Scarface, adding the syllable "JOO" in places it doesn't belong.

Garcia, still playing the role of Falcone, refused to partake in the beating of another cop, a decision which may have blown his cover. Fearing that their agent may be in danger, the FBI pulled the plug on the operation, but by that time, Garcia had gathered enough evidence to send DePalma and several other key Gambino family members away for years.

To add insult to injury, Jack Garcia would have been called out instantly had anyone ever bothered to pat him down. He was wearing a wire the entire time.

Honestly, in an organization where heritage is everything, this is like, we don't know, a black guy going undercover in the KKK.

A Black Guy Goes Undercover in the KKK

The 6 Most Hilarious Undercover Operations Ever Pulled Off

The Case:

With a whopping 6.56 percent African-American population, Colorado Springs, Colorado, is whiter than a John Mayer concert. However, that didn't stop the KKK from placing an ad in the newspaper back in the late 1970s (when the percentage was probably even lower) looking for people in the area to start a local chapter.


We at Cracked aren't exactly criminal masterminds, but at least when we're thinking of starting up an illegal underground crime organization, we have the presence of mind not to announce it in the Denver Post. In a twist that should have surprised nobody, the Klan got a call from undercover cop Ron Stallworth.

The KKK isn't exactly known for its hospitality, so Stallworth knew he would have to put on a good show if he was going to gain entry into their club. In his conversations with other members, he made a point of throwing a bunch of racial slurs into his speech, and complained that his sister had recently begun dating a black man.

Seeing as guys in the Klan are already sensitive to the issue of losing dates with their sisters to other dudes, they were sympathetic to Stallworth's story and got along with him immediately. In fact, he became one of their most valued new members, often conversing with David Duke, former Grand Wizard Klan who later ran for President. Not President of the Klan, President of the United States.

The 6 Most Hilarious Undercover Operations Ever Pulled Off

Yes, they refer to their leader as "Grand Wizard."

As things started getting organized in Colorado Springs, the chapter needed a leader, and they turned to their good friend, Ron Stallworth, to take on the role. However, the group faced one big, black problem.

The Stupidity:

This is Ron Stallworth:

The 6 Most Hilarious Undercover Operations Ever Pulled Off

Stallworth, looking like a cross between Isaac Hayes and Shaft, successfully posed as a "pure Aryan, white man" who had a serious grudge against anyone with skin darker than that of Edgar Winter. Because the vast majority of his conversations with the Klan occurred via telephone, they never caught on to the act. On occasion, Stallworth's presence was requested, in which case he would send a white officer in his place. They never figured it out.

During his talks with David Duke, Stallworth would ask him if he was ever afraid of being infiltrated by a minority. Duke reassured him, stating that he always knew when he was talking to an African-American because black men "pronounce words and letters a certain way," unlike Stallworth, whose creamy vanilla voice could belong only to a pure member of the master race.

William Queen Plays it Stupid

The 6 Most Hilarious Undercover Operations Ever Pulled Off

The Case:

Armed with a legion of creepy Santa Claus beards and fueled by enough cheap beer and Jack Daniels to send Lynyrd Skynyrd on two world tours, outlaw motorcycle gangs have a reputation not to be sneered at. Seriously, don't sneer at them. You'll get a boot to the kidneys.

The Mongols are one such organization, having been rowdy and murdery enough to bring themselves to the attention of the U.S. Bureau of Alcohol, Tobacco, Firearms and Explosives. As an aside, it's very telling that these four things go together so often that they're handled by a single bureau.

The 6 Most Hilarious Undercover Operations Ever Pulled Off

In an attempt to explore the inner workings of the Mongols and bring them to justice, ATF agent William Queen was sent undercover to infiltrate the gang under the alias of Billy St. John. After more than two years as a trusted member, during which time he had to convince his fellow Mongols that he would be willing to kill anyone that stood in their way, Queen was able to provide information to the authorities which led to the arrest of 54 individuals, leading the ATF to say with a straight face the operation was their "most successful penetration."

The 6 Most Hilarious Undercover Operations Ever Pulled Off

"When Agent Queen's long, hard work came to a climax, we were all immensely satisfied."

The Stupidity:

How do you convince a bunch of criminals that you're not spearheading a deep-cover sting operation? You play dumb. Queen played it convincingly--he earned the reputation of the biker gang equivalent of the village idiot, the bikers giving him the nick-name "Billy the Slow-Brained." On a side note, the Mongols absolutely suck at creating nicknames.

The 6 Most Hilarious Undercover Operations Ever Pulled Off

From left: Johnny the Sissy, Brian the Bald, Andrew the I Totally Saw His Dick Once and It Was Like, So Tiny.

You might think that would have made the investigation harder, since most well-run organizations keep the office idiot away from the important stuff. Hell, forget about the cops; if you feed details of your drug smuggling/racketeering/murdering operation to the gang dimwit he may go blabbing about it to the cable repair guy.

Apparently things worked differently in the Mongrels. Billy the Slow-Brained found himself being promoted through the ranks as chapter treasurer, and even became full-on vice president. Hell, the guy turning out to be a cop was probably the best case scenario there.

Whack Dalia

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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.

The 6 Most Hilarious Undercover Operations Ever Pulled Off

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.

The 6 Most Hilarious Undercover Operations Ever Pulled Off

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

Neo-Nazis Just Don't Try Very Hard

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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.

The 6 Most Hilarious Undercover Operations Ever Pulled Off

"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.

The 6 Most Hilarious Undercover Operations Ever Pulled Off

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?

Kindergarten Cop

The 6 Most Hilarious Undercover Operations Ever Pulled Off

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.

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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.

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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.

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