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Lawyer of the Day Stephanie Birkitt: An Update on the Ex-Letterman Lover

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On the media website Mediaite, we are erroneously listed as having an affiliation with the Late Show with David Letterman. We wish! If that were the case, then maybe we’d have inside dirt on one of the juiciest media scandals to come along in a while.
And it’s a media scandal with a legal angle — several, in fact. Last Friday, we named the woman at the eye of the storm, Stephanie Birkitt, our Lawyer of the Day. Birkitt — the former Letterman paramour whose ex-boyfriend, Robert “Joe” Halderman, stands accused of trying to extort David Letterman — is a lawyer. The blonde hottie is a graduate of Cardozo Law School, and she passed the bar exam twice — in New York and Connecticut. Very impressive, Ms. Birkitt!
Alas, Stephanie Birkitt may be a two-timer in more than one sense of the word. We previously stated, relying on other sources, that Birkitt’s sexual relationship with her former boss ended in 2003. Now we’re hearing otherwise, from the New York Post:

Pretty former “Late Show” staffer Stephanie Birkitt revealed in her diary that she continued having sex with boss David Letterman even after moving in with her CBS-producer boyfriend, who later allegedly tried to extort him over the affair, sources told The Post yesterday.

Letterman and Birkitt enjoyed romantic hikes last fall at his sprawling ranch in eastern Montana — where he was married in March — while her boyfriend, “48 Hours Mystery” producer Robert “Joe” Halderman, stayed home in Connecticut, the sources said.

At the time, Birkitt, 34, insisted to Halderman that she and the 62-year-old Letterman had just “a platonic relationship,” a source said.

“I’m his best friend,” Birkitt told the worried 51-year-old Halderman, the source said.

A friend with benefits? Like free law school tuition? Speaking of which, according to our reader poll, almost two-thirds of ATL readers would sleep with David Letterman in exchange for free law school tuition.
UPDATE: According to Maureen Dowd (gavel bang: commenter), Letterman’s company loaned Birkitt the money for law school, which she paid back. If true, this is disappointing. What’s the point of sleeping with the boss if you can’t get paid for it?
More law-related Letterman links, after the jump.


The Post article goes on to note that Letterman, who apparently funded Birkitt through law school, was eager to keep her on his staff (pun intended):

The multimillionaire comic even did his best to keep Birkitt, a graduate of Benjamin Cardozo Law School, on his payroll. After she graduated in June 2008, he offered her a job as his personal lawyer, the sources said.

Birkitt later tried to use the generous offer to persuade Halderman to have children with her, saying she would bring in the bucks in her new job and he could stay home as a Mr. Mom, the sources said.

Talk about a bizarre love triangle! (Also, we’re not sure why Birkitt would be so eager to have babies with Halderman, who’s kinda gross — but to each her own.)
Birkitt came to know Letterman while working at CBS and then The Late Show. She eventually started appearing on air, where she would banter with Letterman, who called her goofy nicknames. Here’s a bit more detail on the Letterman-Birkitt relationship, from People:

Birkitt’s duties [at the Late Show] initially included working with Letterman’s charities and his Indy car racing team, but she got a big on-air break when the show chose her to answer the office phone when Letterman would call on-air.

“We developed some sort of a phone rapport, just like we get along in real life,” Birkitt told the Union Leader. “He teases me and gives me a hard time and I’ll give it back, but overall, he’s super nice.”

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And perhaps he gives her a hard something else, too.

“He’s the best boss I’ve ever had,” Birkitt told Entertainment Weekly in 2002.

And perhaps the best something else, too.
Okay, that’s enough innuendo for one post; there are serious legal issues here too. Check out these links:

  • Over at the National Law Journal, Tresa Baldas interviews employment lawyers about L’Affaire Letterman (and they predictably warn that sleeping with subordinates is fraught with peril).
  • Over at the WSJ Law Blog, Ashby Jones chats with law professor Paul Secunda, of the Workplace Prof Blog, about the elements of a sexual harassment claim.
  • Over at Am Law Daily, Brian Baxter reports on how CBS will be handling its investigation of Joe Halderman, the CBS employee charged with attempted extortion.

Speaking of Halderman, the man accused of trying to extort $2 million from Letterman, an ATL tipster tells us this information (via a friend who knows Halderman from CBS):

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Joe was apparently a pretty high-strung fellow who spent a lot of time covering news stories in Iraq and around the world. This [news about the alleged extortion plot] was not a shock to those who knew Joe. My CBS friend thought of sending Halderman a Hallmark card saying something like: “Better luck next time with your extortion plans.”

(Obviously joking, as we both think Joe’s no different than someone who holds up people at gunpoint….)

Well, that’s assuming the charges are true. And even though the evidence looks compelling, Halderman has pleaded “not guilty” and retained Gerald Shargel, one of the best criminal defense lawyers in the business.
Regardless of what a jury decides — assuming this ever reaches Twelve Angry Old Ladies, which we see as highly unlikely (but wouldn’t that be fun?) — at least one old lady is not a Halderman fan:

“Late Show” staffer Stephanie Birkitt “was stupid” to ever go out with CBS News producer Robert “Joe” Halderman — who is now charged with shaking down David Letterman for $2 million by revealing the talk-show host’s affair with Birkitt, the staffer’s granny told The Post today.

“People make mistakes and that was one of hers,” Irene Boyle said of her granddaughter Birkitt’s long-term romantic relationship with the 51-year-old Halderman. “Joe was a mistake.”

Boyle, who turns 91 on Oct. 25, said, “I think she was stupid to go out with him.”

…. “They were just good friends,” Boyle said, speaking at the assisted living facility in Newport, NH, where she resides.

Granny Irene, please don’t read the newspapers or watch TV for a while. You don’t want to give your 91-year-old ticker any unnecessary stress.
As for Stephanie Birkitt, she has gone into hiding and hired a lawyer of her own. She must be going through an incredibly stressful period right now.
But Birkitt, despite all the craziness, is better off than many. Thanks to Dave Letterman, her law degree is fully paid for. And unlike many lawyers in America, even if she has been told not to show up to work, it seems that officially she at least still has a job.
Hang in there, Steph. And if you’d be willing to be interviewed for ATL — perhaps for “Career Alternatives: Sleeping With a Millionaire Talk Show Host”? — feel free to drop us a line.
P.S. If you know Stephanie Birkitt personally and have information to share, please email us. Thanks.
Letterman’s gal cheated on new beau — with Dave! [New York Post]
David Letterman’s former staffer Stephanie Birkitt wrote lust letters to ‘Late Show’ host [New York Daily News]
Stupid Human Tricks: On David Letterman and the Law [WSJ Law Blog]
CBS GC Says Letterman Affair Will Be Handled Internally [Am Law Daily]
Don’t play like Letterman, employment lawyers warn [National Law Journal]
Earlier: Lawyer of the Day: Stephanie Birkitt, Cardozo Law Grad and Ex-Letterman Lover

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