14 Insane Stories of Cops Who Went Deep Undercover For Years At A Time

There are plenty of movies or TV shows about cops who had insane undercover operations to bust all sorts of criminals - and while these tales seem too crazy to be true, some are real. There are plenty of real-life examples of cops going deep undercover in the pursuit of justice.

Sometimes in order to crack the case, law enforcement officials have to put themselves in some serious danger and investigate from the inside. For undercover cops, revealing their true identity could not only cost them their job but possibly their life. Cops who went deep undercover have taken down drug lords, hate groups, and even busted animal fighting rings. These crazy stories from undercover cops are true and often had huge impacts for all those involved. Cops who had insane undercover operations were often left shattered, isolated, and alone, rather than rewarded.

After having already spent 24 years with the Orange County Sheriff's Office and other agencies, Robert Killian took on the challenge of his life when he accepted an assignment with the intelligence division to go undercover to investigate white supremacist bikers in central Florida. Killian, who calls himself "Doc," donned leathers and jewelry and rode his Harley to bars frequented by the Outlaws motorcycle gang and the 1st SS Kavallerie Brigade, the Aryan Nation's motorcycle gang.

Slowly, over the course of seven years, Killian ingratiated himself with the gangs and built relationships with August Kreis, the head of an Aryan Nations splinter faction called Christian Identity, who offered him membership. He was worried that his cover might not hold, but became extremely concerned when he learned the Aryan Nation's deputy director was a police officer.

Killian eventually amassed enough evidence to bring down six key members of the Outlaws and the 1st SS Kavallerie Brigade and force the resignation of the racist cop. Unfortunately, it wasn't easy to leave the biker life behind just because the job was done and Killian lost his wife, his family, and his career in law enforcement.

When the target of an undercover ATF operation started asking around for a hitman to take out the informant that helped put him behind bars, the agency realized they had no other option but to insert one of their own undercover agents into the overcrowded prison to pose as said hitman. "Lenny," an ATF agent with experience as an undercover operative, volunteered to do time in the prison as a convicted criminal in order to stop the convicted drug dealer from contacting someone else to pull of the hit.

Though the operation was "meticulously" planned, Lenny admitted he "didn't think this through" as he was being strip-searched for admittance to prison, where not even the guards would know he was secretly an ATF agent. And, despite things going wrong - a storm caused the surveillance system to black out making Lenny vulnerable - word got around to the drug dealer that Lenny was a hitman who made good on his promises and he received the contract to take out the informant.

News of the informant's (faked) death was inserted into a newspaper that was sent to the jail and Lenny got the admission of guilt he needed from the drug dealer, who said on tape: "I love you, man. I owe you my life." The drug dealer got a murder solicitation charge added to his drug charges and Lenny retired from undercover work.

Undercover operatives can't just look the part of an outlaw; they often have to engage in the practices of the criminal organizations they are trying to infiltrate in order to gain entry. Unfortunately, that holds true of both human operatives and, in some cases, animal operatives, as well.

In 2008, Missouri Highway State Patrol officers Terry Mills and Jeff Heath were working with the FBI to infiltrate dogfighting rings with ties to "domestic terror groups." The duo continued investigating the ring under their own agency, with the help of the Humane Society of Missouri. The realized to gain entry to that world, they would have to become active participants themselves. The pair bought, trained, and fought their own dogs, while wearing audio and video recording equipment, in order to gain admittance to the secretive, savage world of dogfighting.

Thanks to their lengthy - and bloody - investigation, a multi-agency task force raided dogfighting and breeding operations in eight states, resulting in the arrest of 26 dogfighters and the seizure of more than 500 pit bulls. The officers said putting dogs in fights was a decision that required "grave discussion," but they knew their mission was just when Tim Rickey, the head of the Humane Society of Missouri's animal cruelty task force, gave them his support. "For me, it was about doing the right thing," said Rickey.

For 14 years, Neil Woods haunted the alleyways of Northampton, England - hair bedraggled, stomach sunken in, shoulders slumped, face sweaty - looking to score heroin. He was great at his job because of his propensity to "sponge" up the mannerisms and language of junkies. Woods "loved the art of deception" and thrived on the danger and estimates that his work resulted in upwards of 1,000 years of jail time for the drug addicts and dealers he busted.

The job took a toll on Woods, however, and not just because he had to leave his wife and children behind for long stretches of time and live in the grimy underworld; he began to feel guilty about busting people who were vulnerable, hopeless drug addicts. He was diagnosed with a form of PTSD called "moral damage" brought on by memories of the pain and anguish of those he arrested. "It's about having done bad things. And I have done really bad things," Woods told The Guardian.

Woods left his job and now acts as an advocate for drug legalization as the UK chair of Law Enforcement Against Prohibition. Woods argues that “drug policy should be about reducing not drug use, but drug harm," a stance that has branded him as a traitor amongst his former brothers and sisters on the force.

Sitting behind a desk was not what William Queen wanted to do in law enforcement, so he accepted one undercover operation after another, infiltrating the Aryan Nation, the KKK, and other groups before landing the gig that made him famous: outlaw biker with the San Fernando Valley Mongols. For two years, he hung out in seedy bars, rode stolen motorcycles, and got into fights with competing biker gangs, eventually becoming a "full-patched" member and rising to the level of chapter vice president.

Queen claims to have abstained from doing drugs while pretending to be a Mongol and describes in his book Under and Alone: The True Story of the Undercover Agent Who Infiltrated America's Most Violent Outlaw Motorcycle Gang the various ways that he got away with not doing them, but he admits to reveling in being "as mean and as violent" as he wanted to be, "the baddest of the bad."

Queen's investigation resulted in the arrests of scores of bikers and the convictions of 53 gang members and earned him the Medal of Honor, as well as celebrity within law enforcement circles and a movie deal. But, if he had to do it all over again, Queen said he would pass because of the danger to his family and the fact that the Mongols are "bigger and ever" than ever thanks to his book.

Richard "The Iceman" Kuklinski was a meticulous, evasive hitman believed to have killed as many as 200 men, mostly for prominent Mafia crime families. Surprisingly, he earned his nickname not for his cold-blooded demeanor, but for his tendency to freeze his victims to obscure their time of death.

Despite knowing that Kuklinski was a hired killer with an insane body count, none of the federal agencies tracking his movements could gather any definitive evidence of his crimes until they inserted an undercover operative in his midst. Enter Dominick Polifrone, a New Jersey cop with as much ice in his veins as his target.

Over the course of 18 months, Polifrone posed as a hardened criminal to earn Kuklinski's trust. The pair met in out-of-the-way places to talk shop and Kuklinski eventually gave up enough information about his crimes - in particular, his use of a cyanide-laced hamburger to kill a gang member - for Prolifrone, the New Jersey attorney general and the Bureau of Alcohol, Tobacco and Firearms to take him down.

Some police offers are natural actors destined to work undercover, while others are "one-offs" that just happen to be the right fit for a particular assignment. Such was the case with "Lizzie James" (an alias), a policewoman for London's Metropolitan Police who went undercover as a murderer and sexual deviant to try to lure a murder suspect into exposing himself.

The full details of James's immersion into her undercover role have not been revealed. However, Paul Britton, the forensic psychologist who briefed her, said that it was essential to her cover story as a perverted murderer that she be able to describe "fantasies involving group sex and simulated rape."

The case against the intended target fell apart and was thrown out of court and James, suffering from psychological problems, weight gain, and loss of sex drive, quit the force. She later sued the Metro Police and received the equivalent of $250,000 in damages.

One of the biggest struggles for undercover police officers is keeping their real lives and their undercover lives separate. When drugs are added to the equation, the lines begin to blur, as they did for Robert Carroll, who went undercover for the secretive Sigma unit of the Greater Manchester Police force as a junkie named "Lee Taylor."

Unlike many undercover cops who manage to fake their drug use, Carroll partook of heroin to excess, smoking the drug every day while undercover, and became a junkie for real. A year after joining Sigma, Carroll reached out to the drugs charity Lifeline for help and tried to wean himself off of drugs and took time off from the force to deal with his depression.

Though he told his supervisors and his police officer wife that he was cured, his boss had him tailed and discovered that he was still meeting with one of the drug dealers he had been investigating while undercover to score. A raid of the drug dealer's home found police-issue items that Carroll had traded for drugs, including his own baton. Carroll was jailed for 14 months for misconduct in public office.

One of the most successful and prolific undercover FBI Special Agents of all time is Joaquin "Jack" Garcia. While other undercover operatives tend to lay low and draw as little attention to themselves as possible, Garcia used his massive 6-foot 4-inch, 300-pound frame to muscle his way into the ranks of several different crime families and into the circles of corrupt cops, often overlapping his investigations with numerous identities.

For more than two years, Garcia posed as "Jack Falcone," an associate to the Gambino crime family of La Cosa Nostra in New York City. His investigation resulted in the conviction of 32 gangsters, including several key members of the family. Concurrently, Garcia posed as a different New York-based mobster and concluded a three-year FBI sting in Florida that brought down four dirty cops.

During the same time frames as his New York and Florida operations, Garcia participated in two separate undercover operations in Atlantic City that targeted corrupt politicians and a Boston sting targeting corrupt cops. According to a veteran law enforcement official who worked with him, Garcia is "the best undercover agent the Bureau has ever had."

While undercover, Garcia posed as a jewel thief mobster who also sold drugs. He played his part so well members of the gamed Gambino crime family took him in and made him a top member in their administration. In 2008, he released an autobiography which was adapted into a film that as of April 2017 has not been released. 

To curb a wave of truck hijackings in New York City that averaged five a day, the FBI transferred Joseph D. Pistone to the city and set him up with a fake identity as a small-time jewel thief named "Donnie Brasco." For five years, Pistone hung around locations frequented by the Bonanno crime family believed to be behind the hijackings, making himself known but keeping a low profile so as to not raise suspicion.

Eventually, Pistone met Benjamin "Lefty" Ruggiero, a "foot soldier" for the family with 26 kills under his belt. The two became friends, with Ruggiero vouching for Pistone at risk of his own life. Ordered to commit murders himself, Pistone had to come up with scenarios to avoid killing anyone and even had the FBI stage a fake killing.

When the family fractured and Pistone was ordered to kill rival leader Anthony "Bruno" Indelicato, the FBI pulled the plug on the operation and attempted, unsuccessfully, to arrest Indelicato. Pistone's investigation resulted in the arrest and conviction of over 100 mobsters and effectively destroyed the Bonanno family, which responded by putting a $500,000 bounty on his head. Pistone is still in hiding with his family. His story was famously documented in the 1997 Mike Newell movie Donnie Brasco starring Johnny Depp and Al Pacino.