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Tiger Woods, Letterman, More Celebrity Hush Money Payoffs: Photos

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Tiger Woods’ ex Rachel Uchitel reportedly had to return the $10M he paid her to stay mum. See photos.

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AP Photos
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Tiger Woods’ former mistress Rachel Uchitel reportedly was forced to return the $10 million he allegedly gave her to stay mum about their affair. See photos of more rumored deals.

AP Photo (4)
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The Celebrity Rehab star was the alleged principal mistress in Tiger Woods’ long line of affairs, and she eventually gave the Daily Mail a tell-all interview. Unfortunately, the interview violated the confidentiality clause of her $10 million settlement with Woods, according to TMZ, and Uchitel was forced to return the generous gift. Now the reality star is said to be fuming that her lawyer, Gloria Allred, struck a deal with Woods’ attorney in order to avoid a damages suit, and Uchitel has hired a malpractice lawyer.

AP Photos
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Celine Dion and her longtime manager-husband are one of those rare long-running celebrity couples, but the two allegedly paid a whopping $2 million to a woman who claimed she had been groped by Angelil in a hotel elevator. While Angelil never admitted guilt in the matter, their lawyer says they made the payment for “personal reasons.” Three years later a grand jury indicted the woman, Yun Kyeong Sung, on extortion charges. 

Jennifer Graylock / AP Photo
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The soccer star may be smooth on the field, but his personal life has been much rockier. Ronaldo had a love child a year ago following a one-night stand with a British student, and reportedly paid her a healthy $10 million to give up her rights to the baby. According to the Daily Mail, the 20-year-old now regrets the decision and wants the baby back.

Gregg DeGuire, PictureGroup / AP Photo
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In the precursor to Weinergate, then–New York Jets quarterback Brett Favre reportedly sent crotch shots to Jets game-day employee Jenn Sterger. The photos were published by Deadspin.com, and Sterger immediately hired attorney Gloria Allred, who represented Tiger Woods’ mistress Rachel Uchitel. Before Favre could fess up to sending the photos, Allred noted that Sterger could still take money from Favre if he offered. “Parties often agree to confidential settlements rather than have one party pursue litigation,” Allred said. Although Favre came forward at a press conference and the NFL fined him $50,000 for failing to cooperate with their investigation, Favre was later sued by two former massage therapists for the team who accused him of sexual harassment.

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Kanye West and model Amber Rose dated for two years before breaking up. While Rose was spotted almost immediately making out with NFL star Reggie Bush in the Hamptons, a source said the couple always was “on-again,off-again” and predicted they would be back together soon enough. While the breakup was pretty quiet, whatever happened between them was bad enough that West allegedly paid Rose $1 million to not discuss their private life in public. But it looks like Rose talking wasn’t the problem: While performing at Coachella a year later, West changed the lyrics of his hit “Stronger” to include “I did anything for a blonde dyke, but she’ll do anything for the limelight.”

Zak Brian, Sipa / AP Photo
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At the end of his life, Michael Jackson was some $500 million in debt, and surely some of it came from all the people he paid off. In 2004, Jackson acknowledged that he paid $2 million in 1990 to a boy who accused the singer of molesting him. Jackson insisted the charges were false, but he said he gave the money to the boy because he was “concerned about my family and the media scrutiny that would have ensued had I fought the matter.” Jackson paid between $15 million and $20 million in a court settlement in 1993 to another boy who had accused the singer of molesting him. Jackson also was said to have paid the mother of two of his children, Debbie Rowe, $900,000 in hush money, although he reportedly stopped paying her after he said she broke the confidentiality agreement. As a stipulation of their divorce, Rowe received a lump sum of $4 million and a mansion in Beverly Hills.

Michael A. Mariant / AP Photo
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Shouldn’t the first rule of hush money be to keep quiet—at least until all the money is paid? Architect Peter Cook and supermodel Christie Brinkley’s divorce made the front pages of the tabloids in 2006, when 19-year-old Diana Bianchi stepped forward and testified that she and Cook had an affair when she was just 18. The hits kept coming for Cook, though, as it later came out that he paid Bianchi some $300,000 to stay quiet about their affair—and the money was taxable. Cook later refused to pay the last third of the funds, though, after Bianchi gave a TV interview and discussed the pair’s sex tape.

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Comedian Louie Anderson learned the hard way that paying someone off doesn’t always stop the story. In 1993, the comedian allegedly propositioned a man, Richard John Gordon, at a Las Vegas casino, and Gordon then tried to blackmail Anderson. Fearing his family-friendly image would be damaged, Anderson paid $100,000, but Gordon wanted more money. When he came back to Anderson for $250,000 in 2000, Anderson went to the authorities, and Gordon ended up being arrested after a high-speed chase with the LAPD. He went to prison for the extortion attempt.

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It’s hard to imagine Oprah paying anyone hush money, given how much she talks about her personal life. But Kitty Kelley’s 2010 biography, Oprah: A Biography, claimed the billionaire talk show queen paid $50,000 to disc jockey Tim Watts to stay quiet about an alleged affair—while he was still married. The book claims that Watts contacted Winfrey in 1989—she has long spoken publicly of an affair she had for years with a married man—and said he had been paid to talk about their affair, and Winfrey then allegedly sent best friend Gayle King to his house with the money. Then, in October 2010, a flight attendant claimed that Winfrey passed out on prescription drugs during a flight, that King slept with a male flight attendant during the same flight, and that the talk-show host went on a racist rant. The flight attendant, Corrine Gehrls, later filed a suit that claimed she was wrongfully fired from Winfrey’s private plane, and she sought $75,000 in damages. The suit was settled out of court, and Winfrey’s lawyer refused to comment.

George Burns, Harpo Productions / AP Photo
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David Letterman has earned praise for his handling of his blackmail plot, although probably not from blackmailer Robert “Joe” Halderman. The Emmy-winning CBS News producer dropped a letter off on the morning of Sept. 9, 2009, at Letterman’s Connecticut address, titled “Privileged and Confidential,” that contained a “screenplay” based on Letterman’s alleged sexual affairs with his staffers. He then asked for $2 million in hush money to keep the screenplay confidential. Halderman had read his girlfriend’s diary, which detailed her alleged affair with the late-night talk-show host. But Letterman refused to pay and went directly to the authorities—and came clean about the affair to his wife, Regina Lasko, and to the public. After apologizing for the affair, Letterman made plenty of jokes at his own expense, and Halderman later pleaded guilty to blackmail. Halderman served four months in jail, and although Letterman became tabloid fodder, Halderman agreed as part of the plea deal not to go public with any of the information he learned about Letterman.

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R. Kelly is no stranger to scandal—anybody remember his trial for videotaping sex with a minor?—but a former staffer alleged the singer did want to keep some things private. In June 2011, Kelly’s former manager Jeff Kwatinetz alleged in a lawsuit that the singer refused to pay him $1 million and instead used that money to pay off people who accused him of sexual crimes. Kawtinetz said he singlehandedly resurrected Kelly’s career after the trial and that Kelly said he couldn’t be paid because “the monies were needed for payments to avoid lawsuits and adverse publicity resulting from Kelly’s alleged [sexual misconduct].” Kelly denied the claims, saying the lawsuit was from a “disgruntled former employee” and was a collection of “half-truths, distortions, and outright fabrications.”

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Is it a hush-money scandal if both parties stay quiet? A lawsuit filed in May 2011 claimed an “A-list celebrity of substantial fame internationally” knowingly exposed a star partner to herpes—but the lawsuit didn’t name either celebrity. In the suit, the plaintiff said he met the defendant in Las Vegas and that the defendant claimed he had no sexually transmitted diseases, although he apparently had herpes, which the plaintiff then contracted. But within a month, the defendant settled for a reported $5 million—and the names have yet to come out.

Don Ganem, U.C.S.F. / AP Photo