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Inside David Letterman's Cheating Scandal and Its Impact on His Long-Lasting Marriage

Oyin Balogun
Apr 09, 2021
09:20 A.M.

David Letterman was at the top of the world in 2009 when he had to reveal his infidelity to his fans. Find out how it happened and the effects it had on his marriage.


David Letterman got drawn into an explosive love triangle in 2009 when a CBS News producer named Robert "Joe" Halderman made attempts to blackmail him with his infidelity.

Unexpectedly, Letterman came clean and was forgiven by the world; however his wife Regina Lasko gave him hell. Years after the scandal, he was still making amends for his wrongs.

David Letterman and his wife, Regina Lasko, arrive to the 2017 Mark Twain Prize for American Humor at The Kennedy Center on October 22, 2017 | Photo: Getty Images

David Letterman and his wife, Regina Lasko, arrive to the 2017 Mark Twain Prize for American Humor at The Kennedy Center on October 22, 2017 | Photo: Getty Images


David Letterman was shocked in 2009 when he found a parcel addressed to him in his car. The parcel contained a note that told the showman that his secrets were no longer that, all with infallible proof.

This was the work of Halderman. The producer had been dating Stephanie Birkitt, a woman who worked as Letterman's assistant on his late-night talk show "The Late Show."


Apparently, Halderman had stumbled upon a diary of Birkitt's, and the ambitious woman had penned down all the details concerning her affair with her boss— a man her boyfriend was envious of. He was furious at first; however, Birkitt convinced him she would end things with Letterman. She didn't.



Having uncovered proof that Letterman was getting sexually involved with women he had worked with on his show, Halderman made a decision he has come to regret.

He had been swimming in alimony debts from three ruined marriages, so he decided he would extort Letterman for his shortcomings.

His method was brilliant— he threatened to write a screenplay centered on Letterman's workplace infidelity and how it determined who progressed and who didn't. The idea of it scared the famous TV host to the bones.


Halderman requested $2 million to keep his mouth shut; however, Letterman had other ideas. He got the law involved discreetly and was assured it was blackmail.

Jay-Z revealed that he was lucky to have a wife who knew that he was not the worst of what he had done.

His attorney met with the producer a couple of times but unknown to Halderman, the meetings were recorded. Letterman ultimately issued the producer a fake check of $2 million, and shortly after, he was arrested for grand larceny.



On the same day of the arrest, Letterman decided to blow his own trumpet. It was October 1, 2009, and the famous host had just returned from a commercial break when he offered to tell the audience a story.

He intimated his fans with all that had been happening to him, leaving out the most crucial information until the end of the telling. As he made his revelation, the crafty man added self-effacing asides and jokes that made it all seem like a stand-up comedy show.


At the end, Letterman revealed the dirt the thwarted blackmailer had on him. He stated categorically that he had been sexually involved with women who worked for him on the show.

After the reveal, he made a joke about how it would be "perhaps" more embarrassing for the women than it was for him. The audience could not stop laughing, and that was all Letterman said about it.



In the days following his revelation, news of his many extramarital affairs surfaced on the internet; however, Letterman's preemptive move countered most of the effects.

Some even praised him for coming clean rather than doing all he could to sweep things under the rug. His wife Regina Lasko was another matter entirely— she was not as forgiving.


They had only been married six months when news of the scandal broke, and though they shared a kid and had been dating for decades before the wedding, he feared she would pack her bags and leave.

She did not, but her forgiveness did not come easily. In an interview with Oprah Winfrey, Letterman revealed that he has slept in various places since the scandal— punishment for his extramarital activities.



Sometime after the scandal, Letterman announced his retirement. He returned to the entertainment world and started a Netflix venture titled "My Next Guest Needs No Introduction."

On one episode of the show, he hosted Jay-Z— someone who, like him, had been unfaithful in his marriage. They discussed the subject of infidelity, and Jay-Z revealed that he was lucky to have a wife who knew that he was not the worst of what he had done.

The two seem to have learned their lesson; however, there are many who think that Letterman did not do enough atoning to those he affected with the toxic environment his sexual favoritism created at his workplace years ago.

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