David Letterman's Sex Scandal Still Feels Unresolved 10 Years Later

On October 1, 2009, David Letterman came back from a commercial break on The Late Show and asked his audience if he could tell them a story. A few weeks earlier, he explained, he'd gotten into his car early one morning and found a mysterious package sitting in the backseat. Inside the package was a letter.

"It says that, 'I know that you do some terrible, terrible things. And I can prove that you do these terrible things,'" Letterman said on the air. "And sure enough, contained in the package was stuff to prove that I do terrible things."

The audience chuckled uncomfortably. At first, he wouldn't say what those "terrible things" were. He carefully omitted them, chronicling what happened next while leaving that critical piece of information unexplained.

Letterman told the audience that he immediately called his lawyer. Whoever had left him the package wanted $2 million to keep quiet about what they knew. He and his lawyer contacted the Manhattan District Attorney's Office, which informed them that the threat constituted blackmail. The lawyer met with Letterman's extortionist a few times, including at least one rendezvous which, unbeknownst to the criminal, was secretly recorded. Ultimately, the man was given a phony check for $2 million. On the afternoon of October 1, a few hours before that day's Late Show taping, the blackmailer was arrested.

The audience laughed and applauded throughout Letterman's monologue, which he peppered with jokes, self-effacing asides, and descriptions of how "terrified" he was about the ordeal. The whole thing felt a little like a stand-up routine. About seven minutes into the segment—having sufficiently positioned himself as the victim—Letterman finally revealed what "terrible, terrible things" his blackmailer knew about him.

"The creepy stuff was," Letterman said, "that I have had sex with women who work for me on this show."

He paused. The studio was silent.

"Now, my response to that is: Yes, I have. Would it be embarrassing if it were made public? Perhaps it would. Perhaps it would," Letterman said. "Especially for the women."

The crowd erupted in laughter and applause.

That's about all Letterman said on the matter. He cut to commercial break moments later, and brought out Woody Harrelson when he came back.

Over the next few days, details of Letterman's affairs came to light in the press. He had apparently been sleeping with Stephanie Birkitt, a 34-year-old who had gone from being an intern on The Late Show to Letterman's personal assistant and had appeared in countless segments, including as a correspondent at the Olympics. The blackmailer, Joe Halderman, was her boyfriend. Another woman, Holly Hester, told TMZ she dated Letterman when she was an intern on the Late Show and a student at NYU.

Letterman was married when he confessed to having sex with women who worked for him. He still is, to Regina Lasko. The two met when she was a production staffer on Late Night with David Letterman; at the time they started dating, he was already in a relationship with Merrill Markoe, his former head writer.

The Monday after he made his confession, Letterman spoke about his infidelities on-air again, apologizing to his staff and his wife.

“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," Letterman said. "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.”

After that, he never brought the incident up on The Late Show again.

The response to Letterman's confession was, essentially, a big, collective shrug. On The View, Barbara Walters lauded him for coming clean and getting out in front of the story, called him "a very attractive man," and emphasized that he hadn't been accused of sexual harassment. “Where do you meet people? In the workplace," she said. "It isn’t sexual harassment."

Writing for the New York Times, Maureen Dowd dismissed the notion that Letterman's behavior constituted anything too untoward, explaining that "the women who got involved with Letterman were not pressured."

"Sexual harassment entails pressuring or penalizing a staffer or making the office atmosphere hostile," she wrote. "There’s no evidence yet that Letterman was guilty of that."

Letterman may not have ever pressured staffers into having sex with him. But that doesn't necessarily mean his behavior deserves the kind of sweeping, all-is-forgiven pass it received.

Birkitt's star rose quickly at The Late Show. After being promoted to his assistant, she became a regular on-air talent, making more than 250 appearances on camera. According to an article in New York Magazine, which cited staffers who worked on the show during Birkitt's tenure, her personal relationship with Letterman was, essentially, an open secret.

How might other female staffers, who weren't sleeping with Letterman, have felt seeing Birkitt's career take off so successfully? Letterman never explicitly dangled sex as a means for promotion at The Late Show, at least not that we know of. But that doesn't mean that—in showing special attention to an employee he had a sexual relationship with—Letterman didn't create an uncomfortable, toxic environment for other women who worked for him.

According to Nell Scovell, who wrote for Late Night in the 1990s, the host did just that. Writing for Vanity Fair in 2009, she said Letterman's trysts with female staffers—which, apparently, weren't limited to just Hester and Birkitt—made working for him uncomfortable. So uncomfortable, in fact, that she ultimately "walked away from her dream job."

"There’s a subset of sexual harassment called sexual favoritism that, according to the Equal Employment Opportunity Commission, can lead to a 'hostile work environment,' often 'creating an atmosphere that is demeaning to women,'" Scovell wrote. "And that pretty much sums up my experience at Late Night with David Letterman."

She continued:

Despite the fact that Scovell's piece ran just weeks after Letterman's on-air admission, it never seemed to gain much traction. At the time, virtually the only entity to back her up—to agree that having sex with some staffers and then showing them preferential treatment in the workplace is wrong—was the National Organization for Women.

"As 'the boss,' [Letterman] is responsible for setting the tone for his entire workplace—and he did that with sex," NOW wrote in a statement. "In any work environment, this places all employees—including employees who happen to be women—in an awkward, confusing, and demoralizing situation."

Why wasn't that a bigger part of the conversation? How did so many commentators, from an immensely popular talk show host to a Pulitzer-winning New York Times columnist, fail to see the problem with a powerful boss sleeping with his subordinates, who—according to another employee—then enjoyed professional privileges? And why—ten years later, at a time when Letterman has a new, big-budget talk show on Netflix—have we still not reckoned with those questions?

Let's imagine if Letterman had made the same confession today. In the post-#MeToo era, we might have reacted differently. So many stories that have come out about sexual misconduct, in Hollywood and beyond, involve fostering a "toxic workplace" for employees. Perhaps we didn't have the tools, in 2009—the collective vocabulary—to identify why Letterman's behavior might have been harmful and demeaning to his employees. As Scovell tells it, that behavior was harmful; it was demeaning. Perhaps, in 2009, we just didn't think it was a big deal.

There's a disturbing trend, when it comes to sexual misconduct, whereby if a celebrity committed some impropriety long enough before the Harvey Weinstein revelations came to light, they seem to escape judgment—at least for a time. Years after Woody Allen was accused of molesting Dylan Farrow as a child, he continues to make movies with major studios and A-list stars. Even though we've known about the infamous footage of R. Kelly having sex with an underage girl since 2002, he wasn't widely condemned until recently. By no means can we compare what they've done to Letterman's affairs; but we could argue that Letterman benefits from the same circumstances. The era in which he admitted to sleeping with women who worked for him, allegedly creating a hostile workplace for his female staffers, happened long enough ago that we've all but forgotten about it. And, in the process, we've tacitly forgiven him.

This isn't to say that Letterman should be cast out of Hollywood, or that he deserves to lose his deal with Netflix. His affairs, while confusing and demoralizing for some of the women who worked under him, appeared to be entirely consensual. But in 2019, it just seems strange, and perhaps unfair, that we've never taken a full accounting of what went on behind the scenes at The Late Show—and, at least publicly, neither has he.

Letterman admitted that he had sex with his employees. He apologized to his wife. But he never apologized to women like Scovell. He never engaged with the idea that he might have made his show an unfair and difficult place for women to work, a place where—intentionally or not—he signaled that having sex with the bosses was a way to get ahead.

As Letterman himself said back in 2009, "if you hurt a person and it’s your responsibility, you try to fix it." Ten years later, it’s worth asking whether he ever really tried hard enough.

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