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The Devil in David Letterman


No one knows what’s going on between Dave and Regina. It remains unclear when she knew about Stephanie or any of Dave’s affairs. Regina had left Letterman’s show long before Stephanie worked for him, but she knew her well; Stephanie reportedly accompanied the family on vacations. One source says Regina had every reason to believe that Dave and Stephanie had always been just friends. Stephanie would talk at length with her Late Show friends about Joe Halderman. “She was really into him,” the source says. “She was very much in love with Joe.” She was blending into Halderman’s complicated family, his two children from a past marriage. That attachment, a source says, made her less threatening to Regina. “Stephanie was someone she trusted,” the source continues. “I’m sure Dave’s wife felt some comfort because Stephanie lived with her boyfriend that she was clearly over the moon for. I think Regina let down her guard. You have to know Stephanie. She just doesn’t seem like the kind of person who’d be sneaking around with your husband behind your back.”

Before going on a one-week production break last week, Letterman was apparently doing his best to keep to a normal routine. One source says he has told producers that whatever happens, he’s confident he did the right thing by not giving in to Halderman. All he can do now is hope that Shargel is bluffing and that the worst is behind him. The most likely outcome of the legal proceedings is that Letterman will allow the D.A. to drop or reduce the charges to avoid a trial and the fresh publicity explosion it would trigger.

Letterman also has his legacy to worry about. Dave has always been both a mammoth talent and a force of self-destruction. For most of his professional life, his darker nature helped create his beloved public image. But if self-loathing was his tragic flaw, then his affairs with assistants on the show may prove to be his denouement. Back in 1982, when Late Night started, Dave told profile writer Bill Zehme his theory of late-night talk-show success: “The reason The Tonight Show succeeds is because people like him,” Letterman said. “They turn on the show to see Johnny. Hopefully that will happen here.”

In that same story, a comedian and close friend of Dave’s agreed. “There’s no hypocrisy in what he does,” Jay Leno said about Dave. “I think he tends to lead his life exactly the same way he behaves on television.”


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