David Letterman knew his life would never be the same after his 2009 scandal — comparing
it to “having killed your family in a car crash.”
Many think that the host did not do enough atoning to those he affected with the toxic
environment he created at his workplace.
In today’s video, we’re diving into the story headfirst!
On October 1, 2009, David Letterman returned 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 in the morning and
found a mysterious package sitting in the backseat.
The package contained a note that told David that his secrets were no longer that.
“It says that, ‘I know that you do some terrible, terrible things.
And I can prove that you do these terrible things,’” Letterman said.
“And sure enough, contained in the package was stuff to prove that I do terrible things.”
The audience chuckled uncomfortably.
At first, David carefully omitted the “terrible things”, chronicling what happened next
and leaving out the most crucial information.
Letterman told the audience that he immediately called his lawyer.
Whoever had left him the package wanted $2 million to keep quiet.
He and his lawyer contacted the Manhattan District Attorney’s Office, which informed
them that the threat constituted blackmail.
It was the work of Robert “Joe” Halderman . The producer had been dating Stephanie Birkitt
a woman who worked as Letterman’s assistant on his late-night talk show.
Apparently, Halderman had stumbled upon a diary of Birkitt’s, and the woman had written
down all the details concerning her affair with her boss.
He was furious at first.
However, Stephanie convinced him she would end things with David.
She didn’t.
Having uncovered proof that Letterman was getting sexually involved with women he had
worked with on his show, Halderman made a decision he has come to regret.
Robert had been swimming in alimony debts from three marriages, so he decided he would
extort Letterman.
His method was … quite something.
He threatened to write a screenplay centered on Letterman’s workplace infidelity and
how it determined who progressed and who didn’t.
Of course, the idea of it scared the living crap out of the TV host.
The lawyer met with Letterman’s extortionist a few times, including at least one rendezvous
which, unknown to Robert, was recorded.
Ultimately, the man was given a fake 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 sprayed
with jokes and descriptions of how “terrified” he was about the ordeal.
The whole thing must’ve felt a little like a stand-up routine.
In the end, having sufficiently positioned himself as the victim, Letterman finally revealed
what “terrible, terrible things” his blackmailer knew about him.
He stated that he had been sexually involved with women who worked for him on the show.
He paused.
The studio was silent.
After the reveal, he joked about how it would be “perhaps” more embarrassing for the
women than it was for him.
It’s possible he didn’t view himself as a catch, but who knows exactly what he meant
by that.
That’s about all Letterman said on the matter.
He cut to commercial break moments later and brought out Woody Harrelson when he returned.
Following his revelation, news of his many extramarital affairs surfaced on the internet.
His preemptive move, though, countered most of the effects.
Some even praised him for coming clean rather than doing all he could to sweep things under
the rug.
His wife, Regina Lasko , was not as forgiving.
The two met when she was a production staffer on Late Night with David Letterman.
It’s worth noting that when they started dating, he was already in a relationship with
Merrill Markoe , his former head writer.
Regina and David had only been married six months when news of the scandal broke, and
though they shared a kid and had been together for decades before the wedding, he feared
she would pack her bags and leave.
She did not, but her forgiveness did not come easily.
Along with Letterman’s family, some of his staffers were largely unaware that the host
had a series of affairs with his employees.
“Some suspected as much, and a few said they knew what Letterman was doing,” wrote
Jason Zinoman , a New York Times reporter.
“There had been rumors among some on staff about Letterman’s flirtations for years.”
The Monday after he confessed, Letterman spoke again about his infidelities on-air, apologizing
to his staff and 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.
“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 confessing, Letterman held a meeting with his staffers to “cope with and avoid
his personal life,” according to Zinoman.
“I was looking for a refuge.
Whether they knew it or not, my staffers were being used to support me,” David said.
“The show was endlessly helpful.”
The TV host later opened up about spiraling into a depression.
Letterman was frank about getting through the scandal as he and writer Steve Young reviewed
the monologue that would address the affairs on air.
“I’m in hell.
I will always be in hell until the day after, when I will go to hell,” the Late Show host
told Young at the time.
The response to Letterman’s confession was a big, collective shrug.
On The View, Barbara Walters praised 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.
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.”
Stephanie Birkitt’s star rose quickly at The Late Show.
After being promoted to his assistant, she became a regular on-air talent, making over
250 appearances on camera.
According to an article in New York Magazine that cited staffers who worked on the show
during Birkitt’s tenure, her 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?
The host never explicitly revealed sex as a means for promotion, at least not that we
know of.
But that doesn’t mean that — in showing special attention to an employee he had a
relationship with — he 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, that’s exactly what
he did.
Writing for Vanity Fair in 2009, she said Letterman’s affairs 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.”
Even though Scovell’s piece ran just weeks after Letterman’s on-air admission, it never
really gained traction.
At the time, the National Organization for Women was 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 was wrong.
“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 in an awkward, confusing, and demoralizing
situation.”
Why wasn’t that a more significant part of the conversation?
How did so many commentators fail to see the problem with a powerful boss sleeping with
his subordinates, who — according to another employee — then enjoyed professional privileges?
As Scovell said, that behavior was harmful; it was demeaning.
Perhaps, in 2009, people just didn’t think it was a big deal.
There’s a concerning trend regarding 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.
The era in which he admitted to sleeping with women who worked for him, allegedly creating
a hostile workplace, happened long enough ago that people have mostly forgotten about
it.
While confusing and demoralizing for some of the women who worked for him, his affairs
appeared to be entirely consensual.
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, where — intentionally or not — he signaled that having sex with
the bosses was a way to get ahead.
Letterman may not have ever pressured staffers into having sex with him, but that doesn’t
necessarily mean his behavior deserves the kind of “all-is-forgiven” it received.
And he agrees.
The host previously admitted to Rolling Stone that the scandal was the lowest point in his
life.
In 2015, he told the New York Times that it should’ve cost him his job.
“At the time, I was largely ignorant as to what, really, I had done.
It just seemed like, OK, 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.”
As Letterman himself said back in 2009, “if you hurt a person and it’s your responsibility,
you try to fix it.”
Thirteen years later, it’s worth asking whether he ever really tried hard enough.