Ray William Johnson: True Story Podcast - David Letterman is in BIG Trouble // The Robert Halderman Scandal

Episode Date: August 29, 2026

In 2009, CBS News producer Robert "Joe" Halderman attempted to extort $2 million from late-night talk show host David Letterman by threatening to expose Letterman’s extramarital affairs with female staff members, information Halderman discovered in the diary of his live-in girlfriend (and Letterman's assistant), Stephanie Birkitt.

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Terms apply. Do you remember when David Letterman, the famous late-night host, got extorted for millions of dollars? So there's this guy Joe, and Joe's around 46 living in Norwalk, Connecticut, and he's a TV producer working for CBS News. And he's produced a lot of TV shows, including 48 hours mystery. He's also won a bunch of Emmys, and so he has a bit of a resume. But Joe also has a problem. He recently went through a divorce, and his youngest kid, now lives really far away in Colorado. So he has to pay a bunch of alimony and child support to

his ex and he can't afford to travel to see his son. So financially and emotionally, he's in a bad place. But then one day in 2004, he meets someone who's going to change his life forever. He starts dating this woman, Stephanie. And Stephanie is around 29 and she works as a personal assistant to David Letterman on the late show. And Stephanie isn't just working behind the scenes. She sometimes appears on the show too, in like some of the skits. You can see her here. So this ends up being a really good gig for her. Now pretty quickly, the relationship between Joe and Stephanie becomes serious. And within a year, she moves into his house and their relationship, it's been going great. And a few more months go by. So it's now 2006. And this is where

things start to get complicated. So the last few years, Stephanie has been secretly smashing with her boss, David Letterman. They started out flirting at work, and then they started seeing each other privately, sometimes late at night in Letterman's office, sometimes at hotels or at one of their apartments, and they would even go on work trips with other staff members, and they would end up smashing secretly. And Joe, he has no idea that she's been sleeping around. And Letterman, he has a long term serious girlfriend, and this girlfriend has no idea he's been hooking up with his coworker. And then, one day, in 2008, Joe is at home, and I don't know if he's snooping around or what, but he finds Stephanie's diary, and he reads it. And in the diary, he finds entries

about the David Letterman affair, and he finds love letters that she had written to him. He also finds out that Letterman had been having affairs with other staff members of his before Stephanie, And I'm not sure if he found that out from this diary or if he found that out just through the grapevine, through rumors. Regardless, Joe gets super pissed off. I mean, his girlfriend has been having an affair with her famous boss for years while she's been living with him? Oh, hell no.

So he goes and he confronts her, and he tells her to pack her shit and get out. But Stephanie convinces him that the situation isn't really what it seems, and she begs him to forgive her and promises to distance her, from Letterman, and ultimately Joe agrees to let her stay. But on one condition, she has to quit her job at the late show. But see, Stephanie, she doesn't want to quit her job, and it's a good job for her. So, for whatever reason, Joe agrees. Stephanie won't quit her job, and they'll stay together

and continue their relationship. And about eight months go by. So it's now 2009, and it's night time and Joe is at home and he looks outside and he sees this $100,000 Tesla pull up. And it's David Letterman dropping Stephanie off at home. And here Joe either sees Stephanie hug Letterman in a romantic way or he sees them kiss. There are actually two different versions of this story floating around. Either way, he doesn't like what he sees. And to him, this proves that Stephanie and Letterman are still hooking up. And worse, he feels like she's been lying to him this whole time. And so eventually, Joe and Stephanie end the relationship, and Stephanie moves out. Now, at this point, that should be the end of things. But Joe, he isn't about to let Letterman

off that easily. He wants revenge. Plus, he wants to make a little money from this revenge. So he comes up with this whole scheme to blackmail letterman. Now, remember how I said he recently went through a divorce and his son lives far away in Colorado? Well, he feels like he can use some of this money from this scheme to travel a bunch and see his son on the regular. So he gets to work on this plan. He starts gathering evidence. He had secretly copied pages from Stephanie's diary, so he gets those copies. He also gets access to her emails.

And he uses all of this material and he writes it into like a screenplay treatment, which is like if you were going to pitch a screenplay to any Hollywood studio, you would first write up a one-page treatment that like summarizes the screenplay. That's what this is. It's just a one-page treatment. And this one-page screenplay treatment is about Letterman sleeping with young women who work on his show in exchange for helping advance their careers. Once the treatment is ready, he takes some photo copies of entries from Stephanie's diary, some photos of Stephanie and Letterman together, and some copies of emails that Stephanie sent Letterman, and he packages it all together with a demand letter. And the demand letter basically says, if you don't want this to be published, you need to pay me a shi load of money. Then he hands the letter over to Letterman's personal driver, who puts it in the backseat of Letterman's car for him. Later, Letterman finds the package in. in his back seat and he reads the demand letter and everything and he's like, holy shit, my reputation. So he calls up his lawyer and his lawyer hits up Joe and arranges a meeting between himself and Joe at a hotel in Manhattan.

And so Letterman's lawyer meets up with Joe and Joe makes his demand. He'll sell Letterman the rights to the screenplay for $2 million. And if Letterman pays him the money, he'll keep his mouth shut about the fact that he sleeps with his staff members. And no actual deal is made at this meeting, so I guess Letterman's lawyer says that they'll think about it, and he leaves. Now, Letterman has no intention of paying this guy $2 million. He's not about to be blackmailed. So he and his lawyer, they go to the Manhattan District Attorney's Office, and they report this whole extortion plot. And so the DA's office starts investigating, and they come up with a little sting operation. They instruct Letterman's lawyer to set up another meeting with Joe, and he does, and they make him wear a wire.

So Letterman's lawyer meets up with Joe, and he hands him a check for $2 million. But the check is actually fake. It'll eventually bounce. Regardless, Joe doesn't know that. He feels like he came out on top in this situation, and he's now $2 million richer. Until Until He goes to the bank

and tries to cash the fake check And later that day Bam, police arrest him And I don't have his mug shot But here is a picture of him In court Now while this case is making its way Through the court system

Letterman still has a problem There's a chance that this whole story Could get leaked to the tabloids And become public and be really embarrassing for him, and maybe his career could take a hit. So Letterman decides to get out ahead of it, and he goes on his show,

and he tells his audience about the whole blackmail attempt. Two and five Canadians will hear the words, you have cancer. That's why every step and dollar raised matters. On September 19th, join thousands in Toronto for the Princess Margaret Cancer Foundation Walk. Challenge yourself, friends, and family to walk 21 colloquy.

in support of life-saving research. Together, we can carry the fire and help create a world free from the fear of cancer. Register today at pmcf walk.ca.ca. Real Canadian Superstore has everything you need this back-to-school season. Save on lunchbox savers like Ziggy's sliced deli-meat products for always 375. And get life brand pure Vita shampoo or conditioner for $8 each. At Real Canadian Superstore, when you're ready, we're ready, with a whole world and more.

And it turns out, yes, in fact, he wants a large sum of money, or he's going to produce this screenplay of all the terrible things that I do. And he admits that the scandal is true and that he did, in fact, have sexual relations with multiple women who worked for him, which is extremely embarrassing for him, and it does become tabloid headlines, but just for a short while. And no, it doesn't, in fact, ruin his career. While eventually Joe ends up taking a plea deal and he pleads guilty to grand larceny and he gets sentenced to six months. Two and five Canadians will hear the words you have cancer.

That's why every step and dollar raised matters. On September 19th, join thousands in Toronto for the Princess Margaret Cancer Foundation walk. Challenge yourself, friends, and family to walk 21 kilometers in support of life-saving research. Together, we can carry the fire and help create a world free from the fear of cancer. Register today at pmcfwalk.ca.ca.ca. In prison.