When Letterman Could Have Lost His Job—and Why

“Looking at it now, yes, I think they would have had good reason to fire me. But at the time, I was largely ignorant as to what, really, I had done. It just seemed like, O.K., well, here’s somebody who had an intimate relationship with somebody he shouldn’t have had an intimate relationship with. And I always said, ‘Well, who hasn’t?’ to myself. But then, when I was able to see from the epicenter, the ripples, I thought, yeah, they could have fired me. But they didn’t. So I owe them that.”—David Letterman, on his revelation of an extortion attempt against him arising from an affair with a staffer, quoted in Dave Itzkoff, “Calling It a Night,” The New York Times, May 3, 2015

With audience applause and pundits’ plaudits ringing in his ears, David Letterman took his final “Late Show” bows the other night. Viewers and readers have been reminded of how much he contributed these last three decades to his narrow but venerable entertainment genre: his mentoring of young comics, his boosts to roots music, the wildly popular and imitated Top 10 lists, his deconstruction of so many of the conventions of the talk-show format.

Largely forgotten, however, is the sex scandal that rocked his career in October 2009, when he disclosed to his audience at the Ed Sullivan Theater that he had reported to the police a $2 million blackmail attempt by a jealous boyfriend of a staffer with whom the talk-show host had had an affair.

From the tone of the many retrospectives published these last few weeks, one would have thought that it was a momentary, inconsequential glitch in an otherwise stellar career. The one person who acknowledges it was far more serious was Letterman himself.

In his recent cover profile in Rolling Stone, Letterman admitted the obvious: that, as a recent retired politician who had appeared on his show said two decades ago, he had caused pain in his marriage, to the point where he feared he had "blown up my family." But in the above quote from The New York Times, he acknowledged that the damage extended from the personal to the professional. For all the sharp jabs he delivered to CBS (and, before that, of course, even more so, to NBC) in the last two decades, he admitted, the network would have been well within its rights to terminate his contract.

That might have been one reason why Letterman said on his finale that CBS President Leslie Moonves had been “more than patient” with him.

It has been heartening to read in these interviews about the talk-show host’s love for his wife Regina, and the realization of his mistake in jeopardizing their relationship. Even now, though, it doesn’t appear that he really understands what his transgression was.

To start with, he did not simply have “an intimate relationship with somebody he shouldn’t have.” As he disclosed to the audience at the time, he had affairs, plural. In other words, it wasn’t a one-night stand, or an affair of the heart, but a pattern of misbehavior over multiple years, with multiple staffers, that created an environment of gossip, favoritism, and unwillingness to tell the boss he was making a big mistake. (Were it a businessman plunged into such a fiasco, Letterman would surely have made great sport of the name of his production company: Worldwide Pants.)

In addition, the on-air appearances by his lover leave the viewer with a queasy feeling in the stomach. What are we to make of this exchange, for instance? HE: "Why are you dressed as Little Bo Peep?" SHE: "Because you made me."

When he broke the news, he began by asking the audience at the Ed Sullivan Theater, “Do you feel like a story?” He then admitted the relationships that opened him up to the blackmail attempt, which he said was “scary.” As to whether this all might have been embarrassing, he said it might—for the female staffers involved. It would not be for another five days before he apologized to his wife and son for the damage this had caused them.

The manner of the disclosure didn’t sit well with Terry O'Neill, president of The National Organization for Women, who criticized the “clueless” Letterman for joking about the matter and casting himself as the victim. She assailed him for infecting the work culture "with uncertainty, gossip, and in some cases, hostility."

“Hostility”—that word lies at the heart of the legal definition of sexual harassment. O’Neill’s statement might sound like so much rhetoric, except it was put in a concrete, situational context by Nell Scovell, a longtime TV industry writer and “showrunner.” (Her substantial credits include writing for Murphy Brown, Monk, The Simpsons, Newhart, and N.C.I.S.; creating Sabrina, the Teenage Witch; and co-authoring Sheryl Sandberg’s Lean In.) In 1988, she walked away from her “dream job” of writing for Late Night after less than half a year, because she doubted that she could “thrive professionally in that workplace.”

In an article for Vanity Fair not long after the scandal broke, Scovell made clear what working in “that workplace” involved:

 “Did Dave hit on me? No. Did he pay me enough extra attention that it was noted by another writer? Yes. Was I aware of rumors that Dave was having sexual relationships with female staffers? Yes. Was I aware that other high-level male employees were having sexual relationships with female staffers? Yes. Did these female staffers have access to information and wield power disproportionate to their job titles? Yes. Did that create a hostile work environment? Yes. Did I believe these female staffers were benefiting professionally from their personal relationships? Yes. Did that make me feel demeaned? Completely. Did I say anything at the time? Sadly, no.”

This was not the type of quid pro quo example of sexual harassment that is the easiest to understand and condemn. But Letterman and his male managers felt that they were operating not a workplace but a happy hunting ground for female playthings, creating an atmosphere unhealthy for business operations and relationships.

Scovell had no interest in lawsuits, nor even in seeing her onetime employer (who, she wrote, told her in her exit interview that she was welcome to return) lose his job. But what bothered her, two decades later, was the continuing underrepresentation of women not just on Letterman’s writing staff, but also on Jay Leno's and Conan O’Brien's: “Out of the 50 or so comedy writers working on these programs, exactly zero are women. It would be funny if it weren’t true.”

It would be interesting to see now whether that stark disparity exists five years later. But then again, everything about the scandal has faded like an old newspaper. Letterman, of course, survived and even thrived (including Kennedy Center honors two years ago), due in no small part to the following factors:

*The extortionist took a plea deal rather than risk a trial that might have embarrassed Letterman further. Had he elected to go to trial, Robert "Joe" Halderman, a long-time producer on the CBS show "48 Hours,” might have produced a continuing round of daily revelations, so specific and rich in detail as to make Letterman and CBS a running joke. The deal worked out between his lawyer and the prosecution assured that no new details would emerge.

*Letterman confessed to the whole thing early on. There was no repeated denial, such as others caught in such scandals (politicians such as Bill Clinton and John Edwards, for instance) engaged in. There was, thankfully, no “I did not have sex with that woman” to land him in Bartlett’s Familiar Quotations.

*An obvious on-air lecher, Letterman could not be accused of hypocrisy. The talk-show host’s winks and banter with the likes of Julia Roberts and Drew Barrymore might have been the most obvious of his on-air flirtations, but they were by no means the only ones. (For example, see this post from the Village Voice.) Any young starlet could expect similar treatment. Hence, there was not the slightest shock that he had been randy.

*This was show biz—what else do you expect? Politicians, generals and corporate heads have lost their jobs over this type of behavior. Letterman survived, in no small part because national security was not breached nor news credibility damaged. Moreover, affairs by entertainers are a dime a dozen these days—unlike during the studio era of film, when stars were guarded by a welter of lawyers and private detectives who ensured that nothing would sully a reputation.

*Confidentiality agreements provided protection not generally seen or understood by the public. Also called non-disclosure agreements, these assist companies, in one context, from taking proprietary information about products to competitors. In the entertainment world, they shield celebrities from tell-air memoirs by close aides, servants, nannies, and the like. Time was when they would groan at the likes of That Girl and Phil (1990), a now all-but-forgotten blabfest by Desmond Atholl that described what it was like to be major domo to spoiled-rotten Marlo Thomas and husband Phil Donahue, or Suzanne Hansen’s You'll Never Nanny in This Town Again, a catalogue of horror stories about working for agent Michael Ovitz and wife Judy. You don’t see that happening quite as much these days. What happens when such pacts are not in place occurred several years ago after Tiger Woods’ wife erupted over his infidelity. It turned out to be more than a single unfortunate incident in which the golf star and his estranged spouse might have united to keep their children from reading about it in the newspapers. The problem was that the women with whom Tiger had affairs were not employees, but instead professional consultants and the like he might have met during business but were not under contract to him, who now were more than ready to line up in front of microphones and proclaim that they had Tiger in their tanks. The chances for embarrassment have risen exponentially with social media as well. In the face of these challenges, even B and C list entertainers have confidential agreements for the help, according to a 2007 Los Angeles Times article.

*Letterman’s audience was too jaded to care. Jay Leno might have won the long-term war for late-night audiences because he appealed to a broader Middle America audience, but Letterman’s core viewership—urban and liberal enough to prize his ironic sensibility—provided him with superior defenses. Priding themselves on their edgy, seen-it-all attitude, how could they be shocked at what he copped to? Many were also New Yorkers, a tribe that not only had given wide latitude to mayors with shaky allegiance to their marriage vows (Jimmy Walker, Rudy Guiliani), but were also deeply grateful to him for bringing the talk-show format and its jobs back to Gotham, 20 years after Johnny Carson had departed for the West Coast.

*Letterman made so much money for CBS that only the prospect of a steeper financial loss stemming from his behavior could have made a difference. Companies are prepared to overlook a lot of problems created by someone who makes them fistfuls of money, even when those problems result from behavior that among ordinary mortals might be deemed spoiled, arrogant, offensive, psychotic, even criminal. It is one reason why Bill O’Reilly continues to survive at Fox News after revelations of off-camera actions that were misleading, piggish, and even violent, not to mention on-camera behavior that is undeniably and irredeemably intemperate and rude. Ultimately, in thinking about the Letterman scandal, the operative number is not 260—the approximate number of times, by 2008, that Letterman’s intern-turned-assistant-turned-lover, Stephanie Birkitt, had appeared on camera to sass her besotted boss—but $271 million, the advertising revenues generated in 2009 by The Late Show. (If you’re keeping score, that’s almost $100 million more than Jay Leno's Tonight Show was making at the time.)

Had any of the above factors not been operational, Letterman could very easily have been fired by CBS, in which case he would not have enjoyed a prolonged, joyful swan song but would have been remembered for a messy end to an achievement-packed career, the way that journalists Dan Rather and Helen Thomas are.

So let Letterman depart, then, older, wiser and chastened by his professional near-death experience. But in doing so, viewers should not forget either why he got into trouble or the continuing dangers posed to American business in general and the entertainment world in particular by the environment in his and all too many other offices in the U.S.

The Letterman scandal occurred not just because of a privileged but aging and insecure star but also because of an old boys’ club, in which he felt comfortable in mixing business and pleasure. The paucity of females among his writers meant that when women won any of the few other coveted staff openings, they would be reluctant to say or do anything to risk their positions.

That closed world continues to operate in Hollywood at large, even as the moving van has aleady taken away from the Ed Sullivan Theater all reminders of Letterman and his staff. Women continue to be so underrepresented among Hollywood directors that, as recounted in this Huffington Post article, the American Civil Liberties Union requested an investigation into the hiring practices behind these stats (women only represent 7 percent of directors, 11 percent of writers, and 18 percent of editors on the most successful films over the past 17 years). 

Progress has actually slowed for women in Hollywood over the past 20 years—a state of affairs that could happen only when people prefer to forget, as they have done with a certain talk-show host chuckling his way into the sunset.