At home in Westchester on Friday, the day after his confession, Letterman was already reconsidering his pledge not to talk about the matter again. He’d been on the phone with several members of his staff and learned what his confession was doing to people at the show. “We had tabloid media offering $1,500 bribes to our security guards for access to any floor in the building,” a Late Show source says. “We had reporters chasing staff members to their cars.” Female staffers were getting called by reporters and asked if they’d ever slept with Dave. The problem, he realized, was the open-ended way he’d confessed. Not naming names may have been the only way to play it on Thursday night. But it inevitably raised more questions. Which women? How many? And, in the case of Birkitt, was the relationship still going on?
When Letterman spoke to a staffer on Sunday night, he hadn’t decided what to do on Monday’s show. “We kind of chatted about, ‘Do we address this on Monday’s show, do we not?’ ” says the staffer. “Dave said that he thought that he might want to say something about it.” No one who talked to him Sunday remembers him specifically saying he also wanted to apologize to his wife. By the time he spoke to his contact at Rubenstein, his mind was made up. He would talk about it again. The question then was what, exactly, to say. Would Dave be funny about it, or serious? “We kind of thought, Do we do jokes, do we not do jokes?” the staffer says. “And then we thought, I think we’ve got to do jokes about it.”
Letterman arrived at work Monday morning with a stack of jokes waiting for him—each one about him being in the doghouse. His car’s navigation lady wasn’t talking to him; he’d give anything right now to be hiking on the Appalachian Trail; he spent the weekend raking his hate mail. The question then became how many jokes to use, and whether to let this subject take over the whole show. “I think he really wanted them to be the right kind of jokes,” says a staffer (a Top Ten list about it had already been nixed). At the regular daily monologue meeting in Dave’s office, the writers presented the jokes, as well as others about other topics. But as the writers and Dave mapped out the monologue, “transitioning onto other subjects seemed impossible,” a source says. “The other jokes just didn’t seem to belong.” The head writers, Justin and Eric Stangel, showed him some pretaped bits to use at the end of the monologue, as they do most nights, “but nothing seemed to fit,” a source says. Dave decided to go straight to a commercial after the last joke. Eventually, the entire fifteen-joke monologue (not counting a quick cutaway to a sneezing monkey) would be about his personal mess, starting with that brilliant, seemingly off-the-cuff intro: “Did your weekend just fly by?”
What Halderman hadn’t counted on was that the self-loathing side of Letterman won out. It always does.
But Dave wasn’t satisfied with just the jokes. In his dressing room before the Monday taping, a source says, Dave told a handful of writers and producers that once again, he’d be talking about the alleged blackmailing at his desk after the first commercial break. The producers and writers cleared out, and Dave sat in his dressing room with a pad of paper, handwriting his notes.
On the air, after the first break, Dave said that his sexual relationships with staffers were in the past, and apologized to the people who worked on the show. “I’m terribly sorry that I put the staff in that position,” he said. “Inadvertently, I just wasn’t thinking ahead.” Then, with rare earnestness, he talked about Regina. “She has been horribly hurt by my behavior, and when something happens like that, if you hurt a person and it’s your responsibility, you try to fix it. And at that point, there’s only two things that can happen: Either you’re going to make some progress and get it fixed, or you’re going to fall short and perhaps not get it fixed. So let me tell you, folks—I got my work cut out for me.” For the first time in the whole sordid business, Dave didn’t get a laugh.
Even before Monday’s show aired, Joe Halderman and his attorney had begun mobilizing. By Friday, Halderman, a 51-year-old producer for CBS News’ 48 Hours, had been identified as the alleged extortionist. Halderman, who had lived with Birkitt for several years, was said to be jilted, desperate for money, or both. At Halderman’s arraignment on Friday, his attorney, Gerald Shargel, told reporters that the story Dave told on television the night before wasn’t the whole story. He didn’t give specifics but suggested there would be more revelations to come.