10 More Crazy Extortion Plots

The attempted extortion of David Letterman has been all over the news since he announced the plot — and his sexual relationships with employees — last week.  

See the 10 craziest plots of all time>>

Extortion is of course nothing new. In theory, there is no easier way to make a buck than threatening to tell the world someone’s most embarrassing secret and then demanding they pay to stop you. 

Unfortunately, that method often ends up with the would-be extortionist in jail or on the wrong end of civil suit.  

Extortion schemes can involve a simple demand of money or favours, or they can play a small part in a huge criminal conspiracy and cover-up.  Sometimes the victim has a lot to hide and sometimes, such as with the attempted extortion of John Travolta following the death of his son, the cases involve people trying to take advantage of someone at their most vulnerable.

No matter the fact, they usually make for fascinating stories of deceit, betrayal and intrigue. From the mob to Bill Cosby, here’s our top 10.  

Click here for 10 seedy stories of extortion >

Bill Cosby

Sex scandals still had some sting when Autumn Jackson and two others were convicted in 1997 for trying to extort $40 million from Bill Cosby. She threatened to tell tabloids that she is his illegitimate daughter unless he paid up.

During the trial, Cosby confessed that he had had an affair with Jackson's mother. After the affair, he gave her mother $10,000 to keep mum. Jackson, however, is not his daughter.

Jackson received a 26-month sentence, and the drama continued. Her conviction was overturned and then reinstated.

Cameron Diaz

A photographer was charged with trying to extort $3.3 million from Cameron Diaz in 2003. Diaz said he threatened to release 'private' modelling photos taken of Diaz before she hit it big.

The photographer, John Rutter, claimed he had just offered Diaz a first right of refusal. That defence did not work and he was sentenced to more than three years in jail in 2005.

Diaz also sued Rutter and won undisclosed damages in a civil suit. Diaz's aggressive tactics paid off -- though some sources say the photos included topless shots, no one besides the parties can say for sure. They never hit the press and the civil court judge issued a permanent injunction prohibiting the sale of the photos.

The Mob

In 1999, three mobsters from New York's Genovese and Bonanno crime families pleaded guilty to extortion and a host of other crimes in connection with a massive mob scheme to illegally inflate stock prices of small companies.

The mob used boiler room tactics and paid brokers at Meyers Pollack to overstate assets and hype the stock of HealthTech, an Arizona health club firm. When the stock peaked, they sold at a profit of $1.3 million.

When HealthTech owner Gordon Hall balked, a mobster allegedly held a knife to his throat.

Rod Blagojevich

In 2006, former Illinois governor Rod Blagojevich allegedly hatched a plot to extort favours from then-Congressman Rahm Emanuel, who is now the White House Chief of Staff.

A federal indictment filed in April of this year says 'Congressman A' -- confirmed as Emanuel -- was the target of extortion after he asked why a $2 million Illinois state grant for a school in his district had not been released.

Blagojevich allegedly told an aide to block the grant and then offered to release the money if Emanuel's unnamed brother -- assumed to be big-shot Hollywood agent Ari Emanuel -- would host a fundraiser for Blagojevich. The plot apparently did not get too far, as it's unclear if the demand ever even reached Rahm Emanuel.

Tom Cruise

Celebrity photo broker David Hans Schmidt contacted Tom Cruise and Katie Holmes in 2007 and threatened to release stolen photos of the couple's wedding in Italy. He demanded $1.2 to $1.3 million for the photos. Cruise immediately contacted the authorities.

Schmidt (a.k.a. 'the Sultan of Sleaze' whose main business was the sex life of celebrities) was arrested by the feds and plead guilty on trial. Schmidt reportedly told the actor's representatives that, 'It would not look good for anyone if the photographs become public' and that he would 'hunt down to hell and back anyone who crossed him.'

He was under house arrest facing up to two years in federal prison when he committed suicide in 2007.

The man who originally gave the photos to Schmidt had no criminal record and received probation.

San Antonio Lawyers

The amount extorted was only about $100,000, but the plot raised a lot of eyebrows.

San Antonio lawyer, the now-suspended Ted H. Roberts, discovered his wife had had affairs with four different men, some of whom she met on an adult dating site. He sent the men legal complaints, telling them they had possibly committed a crime and demanded money. If legal actions were initiated, he said, their families would be alerted.

Sometimes his wife, also an attorney, would deliver the documents herself.

Though Roberts told the men the money would go to charity, it actually helped purchase the couple a new home and finance their law firm. In 2007, husband and wife were convicted for various fraud and extortion-related crimes.

BMW Heiress

The man the European press nicknamed the 'Swiss Gigolo' filmed himself having sex with German's richest woman, BMW heiress Susanne Klatten. The man, Helg Sgarbi, then threatened to make the tape public if Klatten, who is married with three children, didn't pay him the equivalent of about $17.5 million.

It seems that extortion was Sgarbi's day job and Klatten was only one of many wealthy women he'd conned by pretending to be a special Swiss representative in crisis zones. Prior to the sex tape, Klatten had already given him $8.8 million. He fessed up to his crimes and was sentenced earlier this year to six years in prison for extorting a total of $12.5 million from Klatten and three other women.

Ronaldo

Brazilian soccer star Ronaldo broke down and cried when the police interviewed him about a sex scandal.

Ronaldo picked up up three prostitutes in Rio in 2008. Once at the motel, it became clear that the prostitutes were men. One of the men was a 21-year old transvestite named Andre Luiz Ribeiro Albertino who goes by Andreia Albertine. Albertino and Co. allegedly tried to extort $30,000 from Ronaldo to keep the motel visit quiet.

A police officer in Rio explained the incident this way: 'Ronaldo admits the facts. He said he just wanted to amuse himself. That's not a crime.' Prostitution is legal in Brazil.

Ronaldo testified at Albertino's trial last September.

Rick Pitino

A woman was indicted this summer for allegedly trying to extort up to $10 million from former NBA and current Louisville basketball coach Rick Pitino in return for keeping her silence about a tryst the two had.

Pitino, after a long night of drinking, had sex with Karen Cunagin Sypher at a Louisville restaurant in 2003. She later claimed she was pregnant and Pitino supposedly gave her $3,000 for an abortion. (Pitino's lawyer says the money was for 'medical coverage,' not specifically an abortion.)

Pitino says the sex was consensual, though Sypher claimed after she was indicted that Pitino had raped her. Police declined to charge Pitino.

John Travolta

A paramedic allegedly tried to extort John Travolta out of $25 million with a medical document relating to the tragic death of his 16-year-old son in January.

The document was a 'refusal to transport' form that Travolta signed after his autistic son suffered a seizure during a family vacation in the Bahamas. Travolta was asked to sign the form because he originally said he wanted his son flown to a U.S. hospital, but he changed his mind and his son was transported to a local hospital.

The paramedic, Tarino Lightbourne, and his lawyer, Pleasant Bridgewater, thought the form made it look like Travolta was refusing help, and would embarrass the family. It is unclear why the pair allegedly thought Travolta would pay not to have the form released.

The trial is ongoing in the Bahamas. Travolta testified earlier this month. Travolta's lawyer also testified, telling the court the paramedic's lawyer said they would accept $15 million.

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