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 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 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 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.
http://www.cracked.com/article_18562_the-6-most-hilarious-undercover-operations-ever-pulled-off.html
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