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David Letterman Admitted Cheating When $2m Extortion Plot Was Exposed Months after He Wed Partner of 23 Years

Bettina Dizon
Dec 31, 2021
11:20 P.M.

David Letterman revealed to have had several sexual relationships with staff on his show after he was extorted a whopping $2 million under threats that the information of his affairs would be published.

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Over a decade ago, David Letterman told his late-night viewers about his infidelities, making them all laugh, thinking it was a joke. However, the punchline they waited for never came.

He may have been the comedic host of "Late Night with David Letterman," but the television personality couldn't be more serious at that time. It turned out that his revelation came following a man's blackmail and extortion scheme that never saw success.

David Letterman with his wife, Regina Lasko, during a red carpet event. | Source: Getty Images

David Letterman with his wife, Regina Lasko, during a red carpet event. | Source: Getty Images

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LETTERMAN ADMITS TO CHEATING

Three weeks before his admission on public television, Letterman found a package inside his car with a note that read, "I know that you do terrible, terrible things and that I can prove that you do some terrible things." With it was proof of the terrible acts he did and an ask for $2 million in exchange for silence.

As Letterman recalled, the moment was scary because he did not know what to expect next and felt he was in danger. He feared not only for his life but also for his family. During his segment, as told by CBS News, Letterman said:

"I was worried for myself. I was worried for my family. I felt menaced by this, and I had to tell them all of the creepy things that I had done."

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David Letterman at the 92nd Street Y presents Senator Al Franken in conversation with David Letterman at 92nd Street Y on May 30, 2017 in New York City. | Source: Getty Images

David Letterman at the 92nd Street Y presents Senator Al Franken in conversation with David Letterman at 92nd Street Y on May 30, 2017 in New York City. | Source: Getty Images

Instead of giving in, Letterman outed himself on national television and told his audience that he had sexual encounters with several women who worked for him in the entertainment industry. Perhaps thinking a punchline would soon follow, the audience laughed. However, Letterman was not joking.

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It was quite a serious topic, yet Letterman's audience was humored. One of the show's viewers said, "Only Dave could get laughs while admitting to cheating on his wife."

The host met with his lawyer and the blackmailer, who threatened to write a screenplay and a book about Letterman's affairs. However, should Letterman pay the $2 million, the man would forgo the idea. In cooperation with the police, Letterman handed the man a fake $2 million check.

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LETTERMAN'S FAMILY

Authorities were able to arrest the extortionist while Letterman testified before a grand jury. Following the arrest, Letterman thanked the Special Prosecution Bureau of the Manhattan District Attorney's office for the help they had given.

Previously, the television personality revealed that his son became a target for kidnapping by one of Letterman's employees.

Although his image had suffered from the scandal, Letterman's family became the center of attention. He was married to Regina Lasko and had a son, Harry, Letterman's first child. Lasko and Letterman began dating in 1986, following his first marriage and other relationships.

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David Letterman hosts a Special Evening with Former First Lady Michelle Obama at The Streicker Center on October 25, 2017 in New York City. | Source: Getty Images

David Letterman hosts a Special Evening with Former First Lady Michelle Obama at The Streicker Center on October 25, 2017 in New York City. | Source: Getty Images

In 1968, Letterman married his first wife and high school sweetheart, Michelle Cook. Unfortunately, their marriage only lasted nine years before they divorced. In 1982, he started dating Merrill Markoe and stayed in love until the '80s.

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When he started to date Lasko, Letterman did not cut off ties with Markoe, with whom he was cohabitating. Even after their breakup in 1988, they had to work together.

According to columnist Ted Casablanca, Lasko likely knew about her husband's affairs at work. "You don't get in bed with Letterman in any sense, romantically or professionally, without knowing it's going to be a different set of rules," he said.

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LETTERMAN'S RELATIONSHIP WITH LASKO

Like Letterman, Lasko also works in the entertainment industry as a production manager. She first worked with the late-night host in 1987, a year after they met.

In 2003, the couple welcomed their son. At that time, she was 43, while Letterman was 56. Although already with a child and growing older each day, the pair did not feel any pressure to tie the knot until 23 years after their relationship began.

Their intimate 2009 wedding ceremony took place in Choteau, Montana, with a few of their closest friends and family members. The scandal would surface a few months later.

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LIFE AFTER THE SCANDAL

Understandably, Lasko was upset when her husband's scandal broke. Letterman also admitted that becoming a victim of blackmail was "not a happy memory." However, it changed their lives for the better as he worked towards fixing everything for his family.

Letterman is well aware of his mistakes and has no one to blame but himself. Fortunately, his wife chose to forgive him instead of leaving. The past events have since made him want to become a better person for his family, and in the end, it paved the way for him to have a great relationship with Lasko.

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It turns out that the cheating scandal was not the only challenge Letterman and Lasko faced as a couple. Previously, the television personality revealed that his son became a target for kidnapping by one of Letterman's employees, Kelly A. Frank.

Frank revealed that he planned to kidnap Harry and demand a ransom worth $5 million in a statement to the authorities. He also planned to take the boy's nanny so that someone could care for him while held hostage.

Fortunately, the scheme was discovered after Frank shared the details with an acquaintance, who immediately contacted the police. Letterman has since worried about his son's safety, but now he knows Harry can take care of himself at a much older age.

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