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Letterman’s sex-extortion sting
What David Letterman gained by going public with his 'Late Show' affairs rather than paying $2 million
 

“Boom!” said Lane Brown in New York Magazine. “As if David Letterman weren’t already beating Conan badly enough,” his show Thursday night is sure to be a ratings bonanza. Letterman told his Late Show audience how he was the target of a $2 million extortion plot in which the blackmailer—now arrested, thanks to a sting operation—threatened to reveal Letterman’s affairs with multiple female Late Show staffers (watch Letterman’s confession).

The “arrestee,” said Jen Chung in Gothamist, is 51-year-old CBS 48 Hours producer (or ex-producer) Robert "Joe" Halderman, according to TMZ and Radar Online, who lived with one of the women Letterman slept with. The affairs were over before he married Regina Lasko—with whom he has a son—last March, but happened during their long relationship.

David Letterman doesn't seem to be at any "immediate risk of losing either his family or his job,” said Belinda Luscombe in Time, but having sex with employees is a lawsuit waiting to happen. He’s also given a “truckload of material to other comedians—or even his own writers” (his company, after all, is called Worldwide Pants). Still, he’s lucky that “as a blackmailing scheme, it was almost comically bad”—Robert Halderman was threatening to write a tell-all screenplay.

Letterman’s account of his “bizarre experience” was “permeated with jokes,” said Roger Catlin in the Hartford Courant, but it easily “could have been the most uncomfortable 10 minutes” in the show’s history. The audience didn’t know when, or if, to laugh, and he made his on-air confession after a monologue filled with jokes about “Roman Polanski, Mark Sanford, and Sarah Palin, who took him to task for making sexual jokes about her daughter.”

 

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