10 Blackmail Attempts That Totally Backfired

by Marcus Ribeiro

Blackmail is about as old as secrets. The idea of someone using secret information to coerce another into doing what they want exists in all cultures throughout all time. It’s typically frowned upon and certainly considered a crime, but the blackmailer does need to get caught and, often, the victim wants to keep everything on the down low too, which is what makes it so attractive. The thing to remember is that blackmail only works if no one finds out. Sometimes it can backfire spectacularly.

10. The KGB Tried to Blackmail the President of Indonesia with a Sex Tape

One of the most popular sources of blackmail is a person’s sexual history. Individuals and even governments have weaponized sex against enemies for ages. In the case of Indonesian President Sukarno, the KGB thought they had the man over a barrel when they arranged for him to meet up with flight attendants during a visit to Moscow in the 1960s. They had his room bugged and apparently filmed his liaisons.

Sukarno was the first President of the country after it left Dutch control. But it offered a lot of strategic advantages to countries like the Soviet Union and America in the region. The Soviets thought filming him with a flight attendant and releasing it would discredit him and cause him to lose his position unless he bowed to their will. Legend has it he was quite tickled to find out they’d filmed him and asked for a copy of the tape

The CIA tried to do something similar, incidentally. They sought a lookalike to make some pornographic films and, when they failed, they had a mask created in his likeness for someone else to wear. The movie was apparently called “Happy Days” though no one knows what happened to it.

9. Soviets Attempted to Out a Reporter as Gay

Joseph Alsop was one of the most famous reporters in the country during the height of the Cold War. He was a man in the know and he had the ear of major politicians, including even the President. He worked with the CIA to gather intelligence using his job as cover, and his columns were read by millions.

The Soviet government was not a fan of Alsop, and as a covert agent of the CIA, you can imagine why. They seized on an opportunity for blackmail when he came to Moscow, thanks to rumors of Alsop’s sexuality. 

At a time when being gay could end a career, Alsop kept his own sexuality under wraps. The KGB set up the reporter with a man in a Moscow hotel room and then secretly photographed them together. Their intent was to blackmail him into becoming a spy for them. Things didn’t go as planned.

Rather than doing what they demanded, Alsop asked if he could get copies of the photos. He then provided a detailed sexual history to the CIA, which included the Moscow encounter, robbing the Soviets of any ammunition they may have thought they had. Word of the incident made it to J. Edgar Hoover and then the President. But even as those in certain circles came into the know, no one weaponized the knowledge and Alsop’s career was not damaged. In fact, years later, someone would release the photos, but the media sources they sent them to refused to publish them.

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8. Scientology Tried to Blackmail Trey Parker and Matt Stone 

The Church of Scientology has been steeped in controversy for decades. Things in the present aren’t much better and the church finds itself the butt of numerous jokes, with few more brutal than those made on the show South Park.

In 2005, South Park aired an episode entitled Trapped in the Closet that took serious digs at Scientology and its beliefs. The church, notoriously protective, aggressive and litigious, did not take this well. They hired investigators to look into South Park creators Trey Parker and Matt Stone in the hopes of finding dirt on the two men that could be used for blackmail. This included doing records checks and even sorting through their trash

The church denied ever engaging in such behavior, but a leaked memo stated otherwise. However, it seemed as though there was no information to turn up and all they determined were useless details like what catering service they used and the kinds of cars they drove.

7. The FBI Tried to Blackmail MLK into Killing Himself 

The FBI devoted years to trying to bring down Martin Luther King Jr. FBI Director J. Edgar Hoover was apparently deathly afraid that MLK would join up with the Communist party, so they wanted to strike first and bring the man down through any means necessary. That included trying to make him kill himself. 

King was put under surveillance and while no ties to Communism were found, they did find evidence that he had been having extramarital affairs. Hoover decided to use that information, along with tapes, to try to blackmail King a year after his famous “I Have a Dream” speech.

An anonymous letter was sent to King along with the tapes. The letter repeatedly insults him, calling him a fraud and abnormal and an animal. The writer threatened to give the tapes to the churches and the public at large. They went on to say, “there is only one thing left for you to do. You know what it is.” King took it to mean they wanted him to take his own life. 

King quickly deduced that the FBI was behind the letter and, obviously, he didn’t fall for the ploy. Instead, he went on to secure his legacy as one of the greatest civil rights leaders of all time. 

6. The Nestle Pigeon Blackmailer

Tampering with food is an insidious crime that can cause mass panic. We expect the things we eat to be safe, and there’s no rhyme or reason to someone poisoning food at random on store shelves, so it can leave even the best of us shaken. In 1999, a man tried to blackmail Nestle after lacing products like mayonnaise and mustard with cyanide. He threatened to do more unless the company paid him off with $14 million US worth of diamonds. 

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The plan was for Nestle to put the diamonds in little bags around the necks of homing pigeons that would return the loot to him. Instead, police just put a tracking device on the pigeon and followed it to the man’s home, where he was arrested. He got 11 years in prison for his troubles.

5. Jaromir Jagr’s Model Blackmail

The one thing necessary for any blackmail plot to work is the victim giving a damn. That just wasn’t the case with the model who tried to blackmail hockey player Jaromir Jagr after taking a selfie in bed with him.

Jagr, who was 43 at the time, was asleep when the 18-year-old model he was in bed with snapped the pic. It’s unclear whether the model herself or someone else tried to use the photo to extort $2,000 from Jagr. The problem was that Jagr was a single man sleeping with an adult woman. He didn’t care if anyone saw the picture. He told the blackmailer to do whatever they wanted. The photo was released and no one, Jagr included, cared at all.

The only consequence of the whole debacle seemed to be that the model, who was dating a junior hockey player at the time, got dumped by her boyfriend. Apparently Jagr was one of his hockey idols and he was less than amused. 

4. The Staged Illicit Photo of George Ratterman To Get Him Out of An Election

Former pro football player George Ratterman was running for Sheriff of Campbell County, Kentucky, back in 1961. The local mob was not amused by this and didn’t want him in the position which, historically, had been tied to corruption. A new, law-abiding sheriff would be bad news. 

Ratterman’s family was getting threatening phone calls and then, in May 1961, he was kidnapped and drugged. Once unconscious, he was photographed in bed with a stripper named April Flowers. The plan was to blackmail him into dropping out. Instead, the entire plot was exposed and rather than causing him to lose support, it skyrocketed him to the head of the race and won him the election

3. The Failed John Stamos Blackmail 

Next to politicians, celebrities are the likeliest targets of blackmail. They are often wealthy and they have a public persona they typically want to preserve. Someone like John Stamos, for instance, would want to maintain his image of a charming, handsome, but mostly harmless man. In 2010, a couple threatened to blackmail him with photos showing Stamos naked with an underage girl and doing drugs. That would have surely ruined his career.

Rather than pay the $680,000 they demanded, Stamos went to the police. He said there were no photos, and it was all lies. The FBI raided the home of the blackmailers and, wouldn’t you know it, there were no pictures. The couple claimed they did exist and implied the FBI stole them for some reason. In any event, the couple were sentenced to four years in jail. 

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2. A Merchant tried to Blackmail Constance Kopp, Which Led to Her Becoming the First Female Sheriff in America

Constance Kopp was not a woman with whom to trifle. In July 1914, silk merchant Henry Kaufman ran his car into Kopp’s buggy. He caused damage to it but refused to pay, and Kopp was not about to let that happen. She sued him and then began to receive threatening letters. Cronies of Kaufman demanded money from her and threatened to kidnap her teenage sister and sell her into white slavery. Another letter demanded $1,000 or their house would be burned down. 

With the help of the local Sheriff, Kopp was able to implicate Kaufman and his underlings. The Sheriff was so impressed with her resolve, he appointed her Under Sheriff, a job no woman had held previously. 

1. Chevalier D’Eon Tried to Blackmail the King of France and Was Exiled

Few figures in history lived a life anywhere near as interesting as the Chevalier d’Eon. For 49 years, the Chevalier lived as a man and worked in service of the King of France as a diplomat and a spy. Then, for the next 33 years, she lived as a woman. If that sounds a little confusing, it’s because it is.

D’Eon was sent to the British court after the Seven Years War under the guise of being an ambassador but really to spy for King Louis XV. Unfortunately, d’Eon was living large and ended up getting fired for wasting money. Fearing the Bastille, he threatened to spill all the secrets he’d learned in his time as a French spy. 

The British embraced d’Eon openly and the French King paid him off to stay quiet. But he was exiled and could never return home. Years passed and when the King died, his son wanted all documents d’Eon had in return for him being allowed to return home. And d’Eon would then be recognized as a woman. The story was that d’Eon was born a woman and forced to live as a man and soon it was embraced by all. D’Eon went on to become a celebrated member of French society until the American Revolution, when she wanted to work as a soldier again. The idea was not received well for women were not soldiers. She was told to join a convent. Any political influence she’d once had was all but gone entirely. Eventually, they tossed her in jail. The switch had backfired on her this time. 

D’Eon returned to England and eventually lost her pension. She died poor at the age of 81, sharing an apartment with another elderly lady.

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