Across 33 years as a late night talk show host, David Letterman was no stranger to putting famous figures—from actors to politicians—on blast for their bad behavior. Like many comedians of his era, he took particular relish joking about former President Bill Clinton’s affairs, including his romantic liaison with Monica Lewinsky—jabs he felt bad enough about that, in 2014, he named them among the biggest regrets of his career.
Perhaps the celebrated host gained some perspective after going through his own scandal involving workplace infidelities. In 2009, Letterman came clean about his sexual relationships with women who worked for him on The Late Show with David Letterman—but only after a blackmailer threatened to reveal it all for him. Read on to find out more.
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Letterman confessed on the air to inappropriate behavior.
Members of the studio audience for The Late Show airing Oct. 1, 2009 didn’t know quite what they were in for when the host opened with a rather unusual monologue.
Letterman began by admitting that he had had sexual relationships with women on his staff. Though he offered no explicit details of the affairs or who was involved, he explained that he had a good reason for making the confession publicly: Someone was trying to blackmail him over the incendiary information and had demanded $2 million to keep quiet.
His public statement also included an apology to his wife, Regina Lasko, who had been his partner since 1986 before they wed in March of 2009. The couple remain married.
He received a threat in the mail.
Dimitrios Kambouris/Getty Images"This morning, I did something I've never done in my life," Letterman said on his show, according to a contemporary ABC News report. "I had to go downtown and testify before a grand jury."
As Letterman recounted to the audience, around three weeks earlier, he’d received a package in the mail threatening to reveal his affairs with staffers. The package included proof of those relationships.
"'I know that you do some terrible, terrible things and I can prove that you do these terrible things,'” Letterman said, quoting the extortion letter. “And sure enough what was contained in the package was proof that I do terrible, terrible things.”
He went on to say that the “terrible things” included “[having] sex with women who work for [him] on [The Late Show].”
The letter also announced the accuser’s plans to publicly humiliate the comedian—including by writing a screenplay and a book about his exploits—if Letterman didn't pay up, according to The Guardian.
The host went on to describe how he had played along with the blackmailer’s request while working with the police, even writing a phony $2 million check to lure him out.
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The extortionist was a former CBS News employee.
Andy Kropa/Getty ImagesThe identity of the blackmailer became public after he was arrested for depositing the fake $2 million check. It was Robert "Joe" Halderman, a former CBS news producer who worked on the show 48 Hours, who had attempted to extort Letterman.
Halderman admitted to this, describing how he had given the packaged containing the extortion letter and his screenplay draft to Letterman’s driver. He also said that he later met with Letterman’s lawyer on several occasions to discuss a payoff in exchange for his silence, according to CNN.
After his arrest, Halderman apologized to Letterman and his family, including Lasko and their young son Harry, who was then five. He also apologized to one of the women mentioned in the blackmail documents—a 27-year-old with whom Halderman had previously been romantically involved.
The former producer accepted a plea deal that included a six-month jail sentence, probation, and 1,000 hours of community service in order to avoid going to trial.
The star had been targeted by blackmailers before.
Gary Gershoff/Getty Images for PeabodyThe incident marked the second time Letterman was the victim of an extortion attempt. In 2005, Kelly Frank, a man who had worked as a handyman for the TV personality at his ranch in Montana, was arrested for an alleged plot to kidnap Letterman’s son Harry, then a year old.
Though he was not convicted of that crime, Frank was handed a 10-year prison sentence for overcharging Letterman for work done at his ranch. He was paroled in 2018—around a decade after he briefly escaped from prison and was recaptured.
