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.


#6. The FBI Pulls a Reverse Scarface

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.

"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.

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 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.

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.

#5. A Black Guy Goes Undercover in the KKK

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.

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:

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.

#4. William Queen Plays it Stupid

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.

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."

"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.

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.

Recommended For Your Pleasure

To turn on reply notifications, click here


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!