David Letterman took his mistress on vacation with his family


The lawyer for Robert “Joe” Halderman promised that we’d soon learn that David Letterman was not as innocent or as nice a guy as we all thought. He said this in a way that implied it would excuse or explain Halderman for attempting to extort $2 million from Letterman over his long affair with Stephanie Birkitt, Halerman’s ex-girlfriend. Thanks to the National Enquirer, we do have a lot of the details. Unfortunately nothing short of David Letterman committing criminal acts would explain or excuse Halderman’s extortion, so while it’s interesting to read, it doesn’t get Halderman off the hook in the slightest. It’s tawdry but not illegal, so I’m not sure why his lawyer thought it would help.

But, like I said, it’s tawdry. Meaning pretty damn interesting. According to the Enquirer, Dave was having an affair with Stephanie since she started working for him in 1996. It wasn’t a brief or even medium-length indiscretion. It was a long-term relationship. The Enquirer also says Stefanie started seeing Halderman when Letterman’s then-girlfriend/now wife Regina Lasko got pregnant six years ago. She was devastated, because she believed if she got pregnant first Dave would leave Regina and marry her instead. Since that didn’t work out, she started dating Halderman, but never really ended things with Letterman.

Here are some more of the Enquirer’s other bits:

The shameless 62-year-old talk-show host put his girlfriend [Birkitt] in charge of his Indy race car team, brazenly took her on trips with his family, and even had her re-enact his favorite “Stupid Pet Tricks” – with her as the pet, sources say… Insiders says Stephanie has competed with Regina – mother of Letterman’s 5-year-ol son Harry – for the “Late Show” host’s affections since she started working for him in 1996.

“It was like Stephanie was in a secret war with Regina that Regina knew nothing about. Stephanie once boasted, ‘Dave may go home to her, but I’m the one he fantasizes about!’” an insider told The Enquirer… Letterman soon hired Stephanie as a personal assistant and put her in charge of his charity work and his Indy race car team, said the source. “Stephanie knew next to nothing about race cars, but it gave her and Dave an excuse to go away together on so-called ‘official business,’” said the source.

“They’d book separate rooms in five-star hotels as a cover, but they would end up staying together.” …Their affair was nearly exposed when a race car owner caught them acting affectionate at the Indianapolis 500 one year. “Dave was stroking Stephanie’s hair and nuzzling her. Someone told the guy she was Dave’s granddaughter – much to Dave’s chagrin,” the source divulged.

“Stephanie has earned more than $2 million from Dave. He paid her a salary of $200,000 a year, and when she said she wanted to go to law school, he paid her tuition…”

… “Stephanie lied to Halderman and insisted she and Dave were ‘just friends’ – even after she flew with Dave to his Montana ranch last fall to go ‘hiking,’” said the source “And when Dave took Regina and Harry to his villa on the Caribbean island of St. Barts, he invited some staffers including Stephanie, so the two could sneak away together.”

[From the National Enquirer, Oct. 26, 2009, print ed.]

According to the Enquirer, Halderman found Stefanie’s journal last December, and had had it after he found her making out with Dave in his car in their driveway. The two were in the breakup process when Halderman learned Dave was buying Stefanie a house. The Enquirer says that’s what set him off and made him decide to extort Dave for $2 million.

After all, why should Stefanie get a $300,000 home and all Halderman gets is a broken heart? The least the guy is owed is $2 million, just like Stefanie, right? Ridiculousness. This doesn’t change my opinion that Halderman is guilty, and I’m sure it won’t change the New York City D.A.’s either. Or the public’s. BUT… yeah, Letterman comes off as not-so-great now. Taking the mistress on vacation with your wife and little son is just awful. It’s sleazy and terrible and whatever other negative adjectives you want to throw in there. Letterman and Birkitt were together so long I can’t help but wonder who he spent more time with: Stefanie or Regina. And why not just break up with Regina if he cared so much about Stefanie? I understand once he had a son, but before that? Why not just end it and not lead such a sleazy lifestyle? Something tells me Dave gets off on the sneaking around, or he would have.

I still think Letterman’s handled this situation as well as he could. But he should have behaved better from the beginning.

Images thanks to Fame Pictures .

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40 Responses to “David Letterman took his mistress on vacation with his family”

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  1. Teri says:

    Oh, he’s a real prince. Nice guy. Yeah.

  2. Firestarter says:

    Nice example he is to his son of what a man should be-NOT!

  3. Xx says:

    Halderman was stupid and wrong to try to extort, true. Bud DL is a disgusting arrogant prick

  4. BitterBetty says:

    God he sucks. I know two-timing your partner isn’t a novel offence, but that doesn’t make it any less despicable and hurtful. abusing someone’s love and trust is a horrible thing to do. and the worst part is he’s not even sorry. just sorry he got caught.

  5. Jeri says:

    I don’t think any of us know what Dave is feeling, he certainly is not going to announce it and start crying on his show like some politican. I’d be really pi—-d if I were Regina and who knows what has gone on in private with Dave & Regina since this came out. but some things need to be handled in private.

  6. Sudini says:

    Disgusting behavior rules the day. David Letterman has been proven to be a first class ass. I hope Regina leaves him and gets at least half. What a horrible, deceitful thing to do to someone. You’re basically f*cking with someone’s life decisions when you lie on this level.

    I wish the best for Regina and their son.

  7. cowbell says:

    Meh. I still don’t care that he had an affair.

  8. Gigohead says:

    I agree, Halderman was better off selling his story to the tabloids and not resort to extorting the guy. Yes, he would only make a few bucks but at least he would keep his job and not end up in jail!! Duh!!

  9. Jules says:

    How is this news???? A single, unmarried man is cheating on his girlfriend by having an affair with a co-worker? Wow, shocking! For all those with their heads in the sand, this is happening in countless homes across this country right this very minute! Who cares? Move on already…

  10. Feebee says:

    I’m not interested (okay maybe a little) in Dave’s bad behaviour. It’s now between him and his wife. It’s the defence’s tried and true strategy of putting the victim on trial. While Dave’s not a victim in the sense of a rape victim (where victims are heinously and regularly put on trial), he’s still technically the victim of a crime. He hasn’t committed a criminal act that this Joe bloke exposed. This is just another way of saying Letterman drove him to it… it hardly qualifies as a crime of passion.

  11. Bethany says:

    With all the lying, why do we assume it’s extortion? That’s DL’s spin. Halderman would have to be super stupid to take a check. Perhaps Dave was getting the extortion concept out first to claim victimhood.

  12. ccoop says:

    “After all, why should Stefanie get a $300,000 home…”

    Is THAT all he was going to spend on a house for her? Cheap pr1ck.

  13. Delilah says:

    I stopped at he made her re-enact animal skits from “Stupid Pet Tricks”? I guess he really made her his b*tch??? What kind of person actually agrees to that? SICK all around!

  14. fizXgirl314 says:

    Damn, how can someone do that? How can you look at your partner and your mistress in the same instance and not somehow give away that you’re sleeping with both… I mean, it’s one thing to cheat on someone, but to bring the two together and do it right under your partner’s nose? that’s gotta take a man of incredible questionable morals and very little remorse… :/

  15. daniel says:

    Sounds to me like everyone weaved a tangled web of deceit and now everyone is reaping what they had sown. Good, I don’t feel sorry for any of them. You put yourself exactly where you want to be by your actions! remember the days when people used to take responsibility for their actions? Now everyone just makes excuses or blames someone else, how lame! Every bad decision I’ve ever made as a human has come back to bite me in the ass so why not David letterman and all his ilk? Karma is a bitch! lol!

  16. PJ says:

    This is all according to Halderman, the ex-boyfriend and extortionist who has convinced himself that Letterman ought to fork over millions of dollars. He has shown no remorse whatsoever.

    Why should we believe him? Maybe some of it is true, maybe none of it is. Even if Halderman is telling the truth as he knows it, he’s getting all of his information from his former girlfriend, who might not exactly be the best source either.

    The bottom line is, if Letterman wanted Stephanie, he would be with her. Instead he chose to marry Regina and raise their son together. He was very generous to Stephanie, though.

    Maybe it’s Stephanie who’s angry!

  17. TwinkleToes says:

    …And I still don’t give a rat’s taint about this story or David or his busted looking biatches.

  18. Bobby the K says:


    If you ever saw letterman on nbc, you wouldn’t use the word ‘nice’ to describe him. Maybe this is some sort of karmic balancing.

    And this kind of thing would hurt him a lot because he is so private and you can tell how much he loves his son.

    And it has been reported that his mother is devastated, and i would believe that.

    I think we as a society have to accept the fact that what we consider a sacred, meaningful bond or whatever, isn’t really held that sacred after all.

    Some people, i expect a majority of them are men, cannot remain faithful within the confines of a marriage.
    Now what?

  19. TwinkleToes says:

    Bobby, we continue to not give a rat’s ‘taint, johnson, peen or bush about DL and his unglamorous life. That’s what.

  20. minx says:

    Well, this thing is getting better and better. I just can’t figure out why he was continuing his relationship with Regina while having a young, new thing on the side. He was not married at the time, she was not yet pregnant with his child. I guess out of habit, convenience, not being able to choose.. whatever, all of it just stinks.

  21. Lantana says:

    I’m with cowbell. Who cares? I think this is a situation of consenting adults and we still don’t know if Regina was on board. It’s entirely possible that she was aware of the situation and OK with it. Men can be such a pain in the ass. Maybe he’s so ADHD that she was glad to have someone else take him off her hands and give her time to spend more of his money. We just aren’t in their world and can’t possibly know what transpired.

  22. Jazz says:

    Is anyone really that shocked? It’s David Letterman, not a politician. His whole show is based on smut.

  23. Firestarter says:

    He made plenty of jokes about Clinton and his infidelities, acting so superior, so it is fitting that he is outted as the hyprocrite that he is.

    However, I do agree, in the end, who cares? Watch him, don’t watch him, love him, hate him.

  24. Tess says:

    Agreed, Jaybird.

    He’s a sneak, and he gets off hiding behind the “Golly, gosh” unsophisticated guy from Indiana shtick.

    What a schmuck.

  25. Goddess711 says:

    Crash! Boom! Bang! rattlerattlerattle…Oh, is that the sound of David Letterman’s career bottoming out? Cool!

  26. bella mama says:

    i’m on the “who really cares” bandwagon. he wasnt married, i dont really care.

  27. Howie says:

    Newsflash- it’s still cheating when you’re not married, but in a committed relationship.

  28. wow says:

    I think it’s called “having your cake and eating it to”. As long as there are women who are okay with being a “side dish”, there will be DL’s of the world. Its very common. And it works in the opposite scenario having men being okay with being second choice.

    For the most part, I think people are only as faithful as their options. And let’s be even more honest. Even the people who think they are in commited relationships, probably more so than not, their partner is already stepping out on them.

  29. la chica says:

    i wonder who is behind the release of all this dirt? i wonder who stands to benefit from making Letterman look as awful as possible? take a guess.

  30. CIdee says:

    Oh, big deal. Aside from the extortion attempt this is a non-story. I still love David Letterman the celebrity and will watch his show. Good boyfriend? No. But what happens behind closed doors between consenting adults is a pretty boring topic. NEXT!

  31. thedomesticgoddess says:

    Big deal … just another hypocrite who thinks he’s above us regular folk. never cared for him at the best of times … now it’s just all the time.

  32. blind item reader says:

    I can only imagine how the conversation with his mother went…

  33. Kelly says:

    i remember seeing her on the show once as his assistant, and i totally thought……..ya they are fucking
    his wife is blind

  34. Rosanna says:

    Halderman is a criminal. DL is a self-entitled holier-than-thou comedian who used to act superior despite living dirty side stories… you call it a nice man? I do not.

  35. I feel sorry for David Letterman’s wife. She is the real victim here – but if she divorces David, then she’ll certainly have the last laugh.

  36. Raleigh says:

    There are so many assumptions made in all these comments. What no one knows is the real story of Regina and Dave. Why did he marry her just this year? Maybe Regina has known about Stephanie all along. Most seem to assume Regina knew nothing. That’s very hard to believe, especially if Stephanie was around on family trips! Maybe the whole thing was consensual all around. Remember John Lennon, Yoko and the other woman — they were a consensual trio. No one knows.
    For that matter, Regina is this totally hidden figure, it’s virtually impossible to even find a photo of her, let alone her and Dave. And Regina USED to be on Dave’s staff too. She was a writer on his show. (And so was his previous girlfriend.)
    To assume Regina is some victim is out of line.
    Only these 3 know what really went on. In some circles, women allow, consent to such arrangements.
    These comments are judgmental and puritanical.
    Hey, if Mackenzie Phillips was having an affair with her father for years — you know, we never know. And we don’t need to.

  37. NFLer says:

    Wow he’s a sneaky sob. I would have never guessed. I hope Conan isn’t pulling stuff like this too.

  38. Lisa says:

    Clearly there is so much more than what DL admitted to on the air. That is a classic preemptive move – sheepishly admit to the tip of the ice berg and hope you look noble and remorseful after doing so. I hope every little slimy thing he ever did comes out in technicolor. He deserves to be taken down many notches – he is a smirking, soon-to-be-has-been, dirt bag. He should only feel twice the pain and embarrassment that his wife must feel but I doubt he ever will.