David Letterman’s Bizarre Late-Night Love Triangle

The talk show host is shaken up after being shaken down

Drew Friedman's Letterman

What, Me Worry? (Drew Friedman)

You can’t be victimized by criminals, explained David Letterman on the Late Show Monday night. You have to push back.

Outside the fortified walls of the Ed Sullivan Theater, a full moon hung in the sky. Mr. Letterman must have been tired. For the past several weeks, not only had he been pushing back, he’d been putting his back into it, straining against an apparent outbreak of villainy. Along the way, he had helped concoct a secret sting operation against an alleged blackmailer. He had publicly confessed to having sexual relationships with several of his employees at The Late Show. He had apologized for indulging his own animal impulses, and had repeatedly shown a video clip of a monkey sneezing.

“It’s fall here in New York City,” said Mr. Letterman. “I spent the whole weekend, raking my hate mail.”

It was time to perform an earnest apology. “My wife, Regina, she has been horribly hurt by my behavior,” he said. “When something happens like that, if you hurt a person, and it’s your responsibility, you try and fix it.”

The audience applauded.

Life was cyclical, Mr. Letterman had learned. Decades earlier, he had moved to Los Angeles with his first wife, Michelle, to try and make it in comedy. His career took off, and his marriage fell apart. As it turned out, comedy clubs put Mr. Letterman in too close proximity with too many beach girls from San Diego State.

“It was embarrassing and superficial,” Mr. Letterman later said of his behavior, according to The Late Shift, by Bill Carter. “It was just me being a dork: Hey, young girls!”

And, now, here we were again. This time around, just to spice things up, life, that bitch, had given things a new twist—namely, the ominous arrival of a man named Joe Halderman with a big ego, a quick temper and a graying goatee, who came armed with photographs, emails and (in a retro plot twist Jane Austen would approve of) diary entries allegedly detailing Mr. Letterman’s furtive indulgences. “The whole thing is surreal,” said Mr. Letterman on the Late Show. “Normally when I’m shaken down for money, it’s my relatives.”

How had Mr. Letterman, our late-night daddy, gotten entangled with this bozo?

Men often meet each other through their hobbies. Play street hockey long enough, and eventually you’ll meet every would-be puck-head on the Lower East Side. David Letterman and Joe Halderman shared many things. They both rose from obscurity to the top of their fields. They both collected paychecks from CBS. They both spent weekends gorging on the fruits of Connecticut. But most importantly, they both shared a pastime—namely, the periodic bedding down of co-workers, colleagues and subordinates.

‘Network news divisions have a high tolerance for assholes,’ said one source. ‘They can be incredibly useful. But also creepy. And everyone knows exactly who they are.’

Mr. Halderman’s first wife was a coworker. According to sources at CBS, so was his second. He was known among current and former colleagues at CBS as a relentless flirt. “Ironically, given his blackmail threat to Letterman,” the Daily Beast recently reported, “Halderman carried on extramarital romances both in the office and on the road, colleagues say, and didn’t do much to hide them.”

Mr. Letterman, for his part, was no stranger to conspicuous interoffice affairs. For roughly a decade, ending in the 80s, Mr. Letterman dated Merrill Markoe, who was then head writer on his show. Earlier this year, Mr. Letterman married his longtime partner, Regina Lasko, a former staff member. On Friday afternoon, following Mr. Letterman’s initial revelations, Ms. Markoe wrote on her blog that “this is a very emotional moment for me because Dave promised me many times that I was the only woman he would ever cheat on.” Later, she responded to comments from her readers with a toast to them: “May none of you ever wake up one morning to find your name and photo included in a montage full of interns and personal assistants.”

There are currently no female writers on staff at The Late Show. But almost overnight, any woman who had ever worked for Mr. Letterman was cast into the game of did she or didn’t she. On Friday morning, one of Mr. Letterman’s former assistants promptly jumped on Facebook and updated her status: Jennifer “swears she only fetched coffee.”

The Late Show and 48 Hours Mystery, where Mr. Halderman worked as a producer, occupy separate and distinct worlds within CBS. What they have had in common over the years is a steady trickle of young, fresh bodies, interns and pages, who occasionally pass between the two TV shows, looking for a good place to start a career. Eventually, Mr. Letterman and Mr. Halderman’s devotion to water-cooler skirt-chasing led them to the same woman.

SEE ALSO: Andrew Cuomo Releases ‘Top Ten’ List for David Letterman

Mr. Letterman discovered Stephanie Birkitt first. He plucked her out of the post-collegiate hordes and put her on TV (a nice perk, which, in addition to the modicum of fame, comes with a paycheck for each appearance). An affair blossomed.

At some point, during her early career explorations, Ms. Birkitt also did a stint working with 48 Hours correspondent Erin Moriarty, who at the time regularly teamed up with Mr. Halderman. Introductions were made. And a second office romance eventually kindled.

Thus began a TV love triangle worthy of Melrose Place.

Within 24 hours of Mr. Letterman’s first, on-air confession, on Thursday, Oct. 1, the Internet was awash in YouTube clips of Ms. Birkitt performing bit routines on The Late Show. In the most memorable one, Mr. Letterman goads his lithe blond friend into making fun of the dancing style of her former boyfriend—some guy she had apparently dated for a couple years as an undergraduate at Wake Forest University. While Paul Shaffer and the CBS Orchestra played a Rod Stewart tune, Ms. Birkitt, wearing a powder blue shirt and jeans, performed a dippy-looking dance, and Mr. Letterman chortled. It was a recurring routine, which tickled Mr. Letterman every time. “I love thinking about the boyfriend being steamed,” said Mr. Letterman, smiling. The segment was called “Would You like to Eat a Sandwich in Dave’s office?”

People stand outside of the Ed Sullivan Theater during a taping of the Late Show with David Letterman on January 2, 2008 in New York City.  (Photo: Bryan Bedder/Getty Images)

People stand outside of the Ed Sullivan Theater during a taping of the Late Show with David Letterman on January 2, 2008 in New York City. (Photo: Bryan Bedder/Getty Images)

WHAT ELSE WAS Dave feasting on backstage in the hushed solitude of his private office?

If the question haunted Mr. Halderman in recent months, he could be forgiven. After ostensibly breaking it off with Mr. Letterman a few years ago, Ms. Birkitt had started dating Mr. Halderman, and they had eventually moved in together. Not long ago, however, the relationship had begun to dissolve. According to various press accounts, it was at this point that Mr. Halderman learned of Ms. Birkitt’s past affair with Mr. Letterman. Was it possible that Mr. Letterman and Ms. Birkitt were still romantically involved?

Such is the plight of a jealous lover. The imagination wanders, the stomach turns, the blood rises. And there, anytime the TV was on, was Mr. Letterman, laughing. “People commit crimes over sex, money and religion,” Jonathan Alpert, a New York–based psychotherapist, recently told The Observer. “A lot of the time, it’s irrational.”

Mr. Halderman, by all accounts, was facing money problems in addition to his romantic woes. He owed roughly $6,000 a month in child-support payments to his ex-wife, and held a series of mortgages. According to the Associated Press, he was making somewhere around $214,000 a year from the network—the same network that was enriching Mr. Letterman to the tune of tens of millions of dollars a year for telling jokes from the safety of a studio. What did that say about our society? Was that fair? Mr. Halderman had risked his own life in war zones for CBS countless times, and seen close colleagues injured. And for what?

He had won a bunch of Emmys. He had written and directed a critically acclaimed documentary for Showtime, called Three Days in September, about Chechen rebels occupying a school full of hostages. He’d earned the respect of his news division. And yet. Who had ever heard of Joe Halderman? One of the casual injustices of television news is that the people who do the most work on breaking stories often get the least amount of public credit. “I don’t think a lot of people go into foreign news producing to attract women,” Marisa Guthrie of Broadcasting & Cable recently observed on MSNBC’s Countdown.

And what about those who do?

“I think being the boy Friday to an anchor star can be kind of castrating,” she added.

The love triangle gone horribly awry is a reliable staple of 48 Hours Mystery, the show Mr. Halderman has worked on for the past several years. As any casual observer of the series would know, there are many things that can make a love triangle combust, that can set one male primate against another in an ugly battle for domination. Feelings of impotence, and a belief that your lover’s other lover is feeling superior to you, pretty much spell trouble.

At some point, Mr. Halderman must have taken measure of Mr. Letterman. Take away the camera, and who the hell was this guy, really? An overpaid dude who put too much value on his own privacy?

Things exploded.

IN THE AFTERMATH of Mr. Halderman’s arrest on Thursday, Oct. 1, on charges of attempted grand larceny, suddenly everyone at CBS News was a wannabe 48 Hours producer—sorting through the facts of the case, formulating possible motives, weighing conflicting evidence and marveling at the sheer madness of the human condition. Everyone had a theory about the alleged crime.

One popular belief was that the same sense of confidence and invincibility that made Mr. Halderman a great war producer had also allowed him to try and allegedly blackmail the late-night star of his own network, despite the seemingly horrendous odds of pulling off such a crime.

Here and there, people talked of the problematic archetypes of the business. One source who has worked at all three network news divisions said that the cocky, swashbuckling hard-news producer who is a genius out in the field and something of a menace back in the office is a common type in TV news. Daring bravado can be a huge asset in a war zone and a major headache when applied to a less volatile atmosphere. Like, say, an office Christmas party. The professional upside tends to justify whatever messes get created along the way.

American talk-show host and comedian David Letterman sits at his desk on the television series 'Late Night with David Letterman,' New York, New York, 1986. (Photo: NBC Television/Courtesy of Getty Images)

American talk-show host and comedian David Letterman sits at his desk on the television series ‘Late Night with David Letterman,’ New York, New York, 1986. (Photo: NBC Television/Courtesy of Getty Images)

“Network news divisions have a high tolerance for assholes,” said the source. “They can be incredibly useful. But also creepy. And everyone knows exactly who they are.”

In years past, the demand was particularly strong at the networks for gung-ho, fearless producers to work in the overseas bureaus. Who better to drop into a war zone on a moment’s notice? But as news budgets have diminished and overseas bureaus have atrophied, more and more of the cowboys have been coming home from the front. Give them too much downtime, goes the theory, and problems inevitably materialize. Golf, which Mr. Halderman enjoyed playing, is an imperfect sedative.

There was also a lot of chatter among the CBS diaspora about the fake check. On Sept. 30, a lawyer for Mr. Letterman, working in conjunction with the Manhattan district attorney’s office, met with Mr. Halderman and handed over a fake check for $2 million—a check that Mr. Halderman promptly deposited in his bank account. Afterward, he was arrested. Who ever heard of someone conducting blackmail by check?

The district attorney’s office was of little help in clearing up the mystery. Whose idea was the fake check? A spokesperson for the DA’s office declined to comment to The Observer. Had the DA’s office ever issued a fake check to a suspect in the past? Again, no comment.

Mr. Halderman’s lawyer was similarly opaque. On Monday morning, Gerald Shargel appeared on NBC’s Today, where he indicated their legal strategy would be to put Mr. Letterman’s behavior under the microscope. “It’s not only the motive, intent and conduct of Joe Halderman, it’s the motive, intent and conduct of David Letterman,” said Mr. Shargel. “I look forward to cross-examining David Letterman.

“David Letterman didn’t give his side of the story,” he added. “David Letterman gave what he wanted the public to know. … He’s a master at manipulating audiences. That’s what he does for a living.”

So what was Mr. Halderman’s version of the events? Was it possible that Mr. Letterman’s affair with Ms. Birkitt had continued through her relationship with Mr. Halderman (as the New York Post reported on the morning of Oct. 6)? Was it possible that Mr. Halderman had found out about the affair and confronted Mr. Letterman? Was it possible that Mr. Letterman had led Mr. Halderman to water? During his media blitz, Mr. Shargel, the lawyer, played coy. He offered few details. His protestations of innocence seemed foggy at best.

In the meantime, Mr. Halderman was out on bail, ducking the ravenous media. And likewise, Mr. Letterman was back in the Ed Sullivan Theater, defending his staff from the vulturous press. On Monday night’s show, Mr. Letterman said that it was the newspaper and radio and television reporters who were now “pounding his staff”—not him. Those days, he suggested, were behind him.

“Right now,” said Mr. Letterman, “I’d give anything to be hiking on the Appalachian Trail.”