The 5 Craziest Undercover Stories In Police History

Real life will always have Hollywood beat.
The 5 Craziest Undercover Stories In Police History

Being an undercover police officer isn't always as ridiculous as Donnie Brasco, Reservoir Dogs, and Kindergarten Cop make it seem. Sometimes it's even more ridiculous. Time and time again, reality steps up to the plate and shows Hollywood that no matter how hackneyed, absurd, or unbelievable their plots may be, real life will always have them beat. For example ...

The Police Set Up A Fake Rap Label To Snare Real Criminals

As everyone's grandmother will tell you, rap music is all about shooting drugs and doing guns. And the Washington, D.C. police department has at least one of those bases covered, so they decided to start their own rap label, Manic Enterprises, and put the word out that they were also in the market for some crime happenings.

The 5 Craziest Undercover Stories In Police History
In fairness to the cops, these were the Billboard charts at the time.

This wasn't just one guy in a bar bragging about having his own label. They actually set up a fancy studio, complete with high-tech recording equipment, flat-screen TVs, and a soundproof booth. The studio was staffed entirely by undercover cops, including Sergeant Dale Sutherland playing fictional rapper "Ritchie Valdez," who supposedly owned the label. Other officers posed as his girlfriends and bodyguards while Sutherland entertained unsuspecting targets with the studio's stockpile of expensive tequila.

At some point, this all starts to sound less like an undercover operation and more like an excuse for a bunch of cops to party, but it worked. Major drug dealers were soon visiting the studio to sell guns and narcotics, although sadly none of the deals were made in rap format. The police didn't even have to hide their surveillance gear, since it's normal for recording equipment to be lying around a studio.

The 5 Craziest Undercover Stories In Police History
junce11/Adobe Stock
"Why do the speakers and mics say DCPD?"
"We stole them ... during our criming."

They soon snared some serious offenders, including members of Mexico's "La Familia" drug cartel, who really should have checked to see if Valdez had released any tracks. One local crew was so impressed by the plush studio that they decided to rob it, but they accidentally butt-dialed one of the undercover cops, who heard them discussing the whole thing. Let's recap: The studio you were going to rob was an undercover police operation, and you accidentally called the police you were about to rob, and it was while you were actively discussing robbing them. Life really doesn't want you guys to be criminals.

Bob Mazur Spent Years Befriending The Leaders Of Two Crime Empires Before Luring Them All To A Fake Bachelor Party

In the 1980s, Robert Mazur was a U.S. Customs agent tasked with infiltrating the Medellin Cartel, aka Pablo Escobar's Cartel, aka Jesus Christ, That Sounds Like A Really Bad Idea. While most of us would have responded to that assignment by going deep undercover as a guy who just quit the CBP, Mazur adopted the persona of a money launderer and caught a flight to Colombia.

Mazur's work led him to the Bank of Credit and Commerce International (BCCI), a major front for a vast array of criminal enterprises, including the largest money laundering operation in history, arms trafficking, kidnapping, and assassinations for hire. It also organized corporate retreats for terrorists in which Shining Path guerrillas took bomb-making tips from a radical Fatah splinter group, then made friendship bracelets and participated in a wacky obstacle course. During his years undercover, Mazur became a personal friend to many senior BCCI and Medellin figures. Yes, he managed to infiltrate two of the most terrifying criminal organizations in history at the same time.

Once he had enough evidence, Mazur then needed to lure this international group of villains to the States so the American government could arrest them. Fortunately, the criminals were already acquainted with fellow undercover agent Kathy Ertz, who had been posing as Mazur's girlfriend. Mazur and Ertz announced that they were getting hitched, and invited everyone to Tampa for the wedding. Since many of their targets arrived with their wives and children, Mazur quietly let the guys know they were invited to a wild bachelor party the night before the ceremony.

So everyone slipped into limos and headed to a nearby restaurant. Of course, all the staff had been replaced by U.S. agents, and one BCCI exec was so confused by the sudden turn of events that he asked the people handcuffing him why so many of the strippers were dudes. For his exemplary efforts, Mazur was rewarded with a forgettable Bryan Cranston adaptation of his story. And probably a lot of personal pride, we guess.

Cops Used The Most Popular Dude Around To Befriend A Serial Killer In Prison

Jimmy Keene was the sort of teenager you can't help but hate. He was a stereotypically cocky, handsome jock with a pretty girlfriend and a politically connected family in his small Illinois hometown. He was the sort of guy who would challenge you to a tennis match for the fate of the failing rec center. But Keene's life took a downward turn, presumably right after he lost that tennis match to a plucky nerd who believed in himself. Dealing significant amounts of drugs landed him in federal prison for a minimum of ten years.

It looked like the remainder of Keene's youth would be spent behind bars, but his inherent popularity presented authorities with an unusual opportunity. They gave Keene a chance to shorten his stay if he would agree to do something most of us go through our lives trying to avoid: become pals with a serial killer.

Federal Bureau of Prisons
"You'll know who he is. Look for the guy with the clearly serial killer facial hair."

Larry Hall was already in prison for one murder, but the feds suspected that he was responsible for a lot more. That's where Keene came in. If Jimmy could somehow befriend Hall and get him to engage in some fun burial site small talk, Keene would earn himself an early release.

Eventually, through a combination of wits and risk-taking, Keene earned Hall's trust, and the man began to share details of his crimes. After securing some vital evidence, Keene left a message for his FBI contact, and expected to be freed the next day. Unfortunately, his contact didn't get the message in time, and a fed up Keene impulsively started insulting Hall, calling him every prison-appropriate synonym for scumbag that he could think of. This led to a wacky series of mishaps which ended with Keene being sent to solitary confinement, presumably while protesting "But I'm not even supposed to be here today!"

St. Martin's Press
You think they'd have gotten the hint when his book publisher sent in the crew for author photos, but no.

But eventually the authorities intervened, Hall faced justice, and Keene received his freedom. Everything worked out in the end. Well, except for the fact that Brad Pitt has reportedly secured film rights to the story.

The 5 Craziest Undercover Stories In Police History
The Chicago Sun-Times
"One that disappointed millions of fans but performed adequately at the box office."

A Police Officer Exposed A High-Ranking Nazi ... In Another Police Department

This may be hard to believe, but America used to have a problem with neo-Nazis. Crazy, right? Back in the ancient year of 2003, Robert Killian of the Orange County Sheriff's Office was monitoring local white supremacist groups. Armed with a Harley, a leather vest, a bitchin' goatee, and what we can only assume were some very creative racial epithets, Killian hung out at local biker bars and worked the Nazi crowd until he finally snagged an invite to more "exclusive" venues. Killian became especially good buds with August Kreis, the head of a splinter group of the Aryan Nations.

At Kreis' encouragement, Killian applied for Aryan Nations membership, and soon began receiving calls from leaders of the group, often during family time with his kids. He'd run into these guys in public and have to revert to his racist persona even if he was with his wife, which sounds like a terrible premise for a sitcom.

P 2004 ARYAN or Z 7 L WORLD NATIONS ios aii So apis . CONGRESS -OS
Jerome Pollos/Getty Images
"Wait, if this package came here, where did her Valentine's Day gift go ...? Oh no!" *laugh track*

One night, Kreis told Killian that he would receive a call from the Aryan Nations deputy director. This man would have a police radio on in the background, but Killian was told not to worry -- he was a cop. That cop turned out to be James Elkins, an officer in the Fruitland Park department. Killian ended up having to fake a cancer diagnosis to distance himself from the Nazis, but his seven years of soul-crushing work stopped a planned terrorist attack and toppled the leadership of two Florida white supremacist groups. By the time they were arrested, Killian's identity had been revealed, and he's had to look over his shoulder ever since. Oh, and his wife left him because of the strain his undercover work put on their marriage. But at least he put that Nazi cop away! Oh wait, the Nazi cop resigned in 2009? And was caught leaving racist pamphlets on people's stoops? Goddammit, Florida.

An ATF Agent Went Undercover As A Hitman ... Inside A Prison

Drug dealer James Richard Hackley decided to hire a hitman to take out Dave Jackson, the ATF informant who helped put him behind bars, because Hackley had never heard of the sunk cost fallacy. After word reached the ATF that Hackley was asking around for a killer, they sent an agent, "Lenny," to pose as a hitman in the same jail. The plan was to trick Hackley into hiring Lenny, fake Jackson's death, then slap Hackley with the charges. Not even the guards knew that the new inmate was an undercover agent. If you just heard a chime, that's the shenanigans alarm. Shenanigans are inbound.

Word soon spread about Lenny's "reputation" as a hitman. Hackley came knocking on his door and said, "I need this guy taken out. I need him gone forever; I need him, you know, eliminated." For this grim duty, Hackley was ready to pay the princely sum of ... one motorcycle. The fact that Lenny agreed to such stupid terms should have tipped Hackley off, but we're not dealing with criminal masterminds here.

The 5 Craziest Undercover Stories In Police History
Federal Bureau of Prisons
"I pay for every thing in motorcycles. Murders, drugs, cable bills -- everything."

The ATF then got Lenny out of jail so he could perform the "hit," which was lucky, since it's much harder to kill civilians from inside a prison. Lenny went to Hackley's apartment and got the key to the motorcycle from Hackley's girlfriend as a down payment, and then the ATF got to work on faking Jackson's death. They took photos that made Jackson look as if he'd been gunned down in a drive-by, then wrote a fake newspaper article about the "hit." They even put it on the front page of a real newspaper and sent Hackley a copy. Hackley was absolutely ecstatic, and declared, "I love you, man. I owe you my life. I really do." Then he was charged with solicitation of murder for hire, and had another 25 years added to his sentence. He is now presumably plotting to murder everyone responsible for that, prompting the need for yet another undercover operation.

Michael Battaglino is a new contributor to Be sure to check out some of his other work if you enjoyed this article.

Man, these were all such much better than just carrying around a fake badge.

Support your favorite Cracked writers with a visit to our Contribution Page. Please and thank you.

For more, check out Genius Police Work That Caught Criminals Red-Handed and The 6 Most Hilarious Undercover Operations Ever Pulled Off.

You have the right to follow us on Facebook.

Scroll down for the next article
Forgot Password?