Blackmail at Black Rock: The David Letterman Case

Nov 13, 2009 - by Don Fulsom

Updated Sept. 4, 2010

David Letterman

David Letterman

Letterman survives his unmasking as a “creepy” sexual predator

by Don Fulsom

On September 9, 2009, David Letterman ambled out of his multi-million dollar lower Manhattan hideaway and plopped his lanky frame into a waiting limo for the short ride to the Ed Sullivan Theater. To Dave’s surprise, his chauffer handed the CBS TV star an envelope.

The driver had lowered his window to accept the envelope at the ungodly hour of 6 a.m. He apparently thought little about the propriety of the transaction—because the envelope came from esteemed CBS veteran “48 Hours Mystery” producer Joe Halderman.

Yet the envelope was not an innocent handoff of company memos from one Black Rock (CBS Headquarters in Manhattan) biggie to another. Authorities say its contents amounted to an extortion attempt by Halderman.  And six months later, Halderman himself concurred—pleading guilty to second-degree larceny.

In his failed blackmail attempt, the producer was threatening to expose the 62-year-old Letterman’s sexcapades, over several decades, with a significant number (eight or nine are the most prevalent rumored numbers) of far-younger Letterman staffers.  In fact, Halderman’s former live-in girlfriend, 34-year old Stephanie Birkitt, was reputedly among Letterman’s cavalcade of underling bedmates. 

A former Letterman intern, Holly Hester, has publicly admitted to falling “madly in love” with Dave when she worked on his show as a NYU student in the 1990s.  This disclosure apparently played a role in Quinnipac University’s cautious approach to sending any of its students to Dave’s workplace.  Fox News quotes Quinnipac Professor Grace Levine as saying she would “be remiss in just trying to ignore” Letterman’s startling on-air confession that he had multiple affairs with his own employees.

What did Halderman’s infamous envelope contain?  According to authorities, there was a “demand letter” for “a big chuck of money” from Dave; a “treatment for a screenplay;” parts of diaries and personal correspondence belonging to a blacked-out name; telephone records and photos.  In the letter, Halderman tells the gap-toothed comedian his “world is about to crash down upon him” unless he forks over the hush money—later set by the accused blackmailer at $2-million.

Not long after the envelope caper, a Dave-approved sting operation put the 51-year-old Halderman in handcuffs. Wearing glasses, a salt-and-pepper goatee, a gray suit jacket and striped business shirt without a tie, Halderman showed up in a Manhattan courtroom and responded in a clear voice “not guilty” when asked how he pleaded to grand larceny. Assistant District Attorney Judy Salwen accused Halderman of wanting “to destroy the reputation of Mr. Letterman and submit him and his family to humiliation and ridicule.”   

Halderman was freed on $200,000 bond, was forced to keep his distance from Letterman, and faced 15 years in prison. His arrest followed a September 30 meeting in a New York City hotel at which Letterman’s attorney James Jackoway gave Halderman a fake $2-million check.

As part of his March 9, 2010 guilty plea, Halderman will serve six months in prison, four-and-a-half years probation, and complete 1,000 hours of community service. In court, Halderman said, "I feel great remorse for what I've done." Outside of court, he told a news conference, "I apologize to Mr. Letterman and his family, Stephanie Birkitt and her family and certainly to my friends and family,” according to ABC News.

In a statement read by his lawyer Dan Horwitz, Letterman said, “I would like to thank the District Attorney of Manhattan, Cyrus R. Vance, Jr., the former District Attorney, Robert M. Morgenthau, the Special Prosecutions Bureau in the D.A.'s Office, and the New York City Police Department. When they became involved with this case, I had complete faith that a just and appropriate result was inevitable. On behalf of my family, I am extremely grateful for their tireless efforts,"

 Newsday reports Halderman was well-liked by most of his co-workers:  “Per someone who knows him: ‘He was just a nice guy ... I can't believe he was involved in something like this.’” Another colleague is quoted as saying Halderman is “very driven, very smart," and is “a hotdog” – a person who can dependably be dropped into a war zone, face the dangers, and get the story.

 In court papers, Letterman is referred to only as Jackoway’s “Client #1.”  What is obviously Birkett’s name is blacked out of the documents released by a Connecticut judge on October 15. The tabloid Globe says Birkett, a pretty blonde Wake Forest grad—first hired by Dave as an intern in 1996—did not know of Halderman’s scheme.  The paper quotes psychologist Judy Kuriansky as saying that Dave, as a serial cheater, could use a good rehab program:  “It’s clear he’s obsessed with sex and needs serious therapy … he needs to deal with his issues so he can save his marriage.”

Reports indicate the jealous Halderman went bonkers after finding proof of Birkitt’s continuing affair with Dave in Stephanie’s diaries at the modest home the two once shared in Norwalk, Connecticut.  Halderman was also far from pleased to spot his live-in love necking with Letterman in Dave’s car in the driveway of Halderman’s home.  This, indeed, was a strange love triangle gone horribly off-kilter.

 Letterman frequently drove many miles out of his way (he lives with his wife Regina Lasko, 48, and their 5-year-old son Harry in a palatial estate in Westchester County, New York) to give Stephanie a ride home (and, apparently, play kissy-face with her) after the curtain came down on the taping of “Late Night.”

 Letterman and Lasko have a 23-year relationship, though they did not get married until March 2009. Curiously, Letterman first met Lasko when she worked on his show. Lasko reportedly is contemplating a divorce, and Dave admits he has his work cut out for him on the home front.

 What might be up for grabs in a divorce? Letterman boasts an annual income of between $30- to $45-million and is said to be worth about $300-million.  Dave—who’s been coming into our homes late at night for 27 years now—recently signed a new $120 million contract to stay on “Late Night” until 2012.

 After Letterman confessed to his office dalliances, one of his former writers—Nell Scovell in Vanity Fair—said she quit Dave’s NBC show because of alleged sexual favoritism and a hostile work environment.  She said Dave paid extra attention to her and was rumored to be involved is sexual relationships with other female subordinates. 

 None of Dave’s co-workers has ever filed sexual harassment charges against him.  But some legal eagles believe Dave’s on-air confession raises serious questions about whether his actions constitute sexual harassment or an abuse of a boss’s power.

 On his show, Dave himself described his behavior as “creepy,” but—as far as is yet know—no outlandishly perverse acts were committed by Dave at his Manhattan “love nest,” or in his secret “bunker” above the Ed Sullivan Theater.  But Dave is said to have enjoyed having some of his gal pals dress up like college co-eds, preferably like cheerleaders—complete with pom-poms.

CBS stood firmly behind their biggest star from the start of the scandal. 

 Yet, in one sense, CBS’s opinion really doesn’t matter.  That’s because Letterman actually works for his own company—an outfit with the now mock-worthy name, Worldwide Pants.  “The firm has stated that it has a policy on harassment and that Letterman is not in violation of that policy,” according to The Christian Science Monitor.

Why would a canny investigative journalist like Joe Halderman think he could pull off the Letterman plot? The New York Daily News quotes Mike Paul, a P.R. expert who's spent hours on the phone with Halderman discussing Halderman’s work at CBS. Paul is plainly baffled: "(Joe’s) a guy who knows better.  He's very intelligent. He understands investigations of a crime. Has he done stories where people have gotten in trouble doing this? Dozens, probably hundreds."                   

 It now seems that David Letterman can survive as a partly emasculated late night TV comedian—one who now cannot make full-fledged fun of the sexual indiscretions of other celebrities and of politicians.  As David Carr writes in the New York Times:  “Hypocrisy and infidelity, primary colors in the comedic palette, will now require a different skill from Mr. Letterman.  Even seemingly innocuous jokes must travel through many layers—filtered through what the audience now knows about Mr. Letterman and what he know they know about him, before it lands.”

 Here are a few examples of jokes that Dave—a frequent target of his own humor—would probably not be able to tell today.  From Randy Cohen in the New York Times Magazine:  “No. 1 Sign David Letterman is changing his ways:  ‘Mr. Letterman’s office.  Lloyd speaking.’”  From Frank Sciortino, former executive news editor of WINS in New York:  “The tip about Dave’s affair with a female staffer came from the CBS cleaning lady who saw the staffer’s name atop Letterman’s ‘To Do’ list for the day.”  And among’s Top Ten Reasons David Letterman Confessed to Affairs:  “I hear Lady Gaga likes the bad boys.”

Thanks to, here are a few of the funnies Dave would not have been able to pull off—had his propensity for sex with subordinates been known at the time:

  •  "Well, President Clinton has gotten himself a new dog. You know, I think it's changing his life, kind of brightening him up. He's teaching the dog to sit up, to beg, to roll-over, you know, just like he did with the interns."
  •  "I really have to hand it to the White House. Around here we can't even get the interns to work the copy machine."
  •  "No move ever goes smoothly. Today Clinton's brand new desk arrived. He had to send it back, apparently not enough head room."

Noting that Dave held the “franchise” on Clinton/Monica Lewinsky gags, Gawker says “now that everyone knows (Letterman’s) been giving it to members of his own staff, he's going to have to endure the sting of the same jibes from Leno, O'Brien, Fallon, and even poor, forgotten Kimmel.”

What does old Letterman rival Jay Leno think of Dave’s predicament?  Leno says he “wouldn’t trade places with (Letterman) now for anything.” But the NBC star adds in an interview with Broadcasting and Cable that he doesn’t think the scandal will hurt Dave too much because, "Dave has never set himself up as [a model citizen]. If it were me, it would kill me. I'm the guy who's been married 29 years. But Dave has never pretended to be Mr. Moral America, he's never set himself up that way."

Halderman, who pleaded guilty to attempted grand larceny, was released from prison in early September 2010 after serving four months of a six-month sentence. While on Riker’s Island, Halderman was the prison librarian.

The convicted blackmailer got out early for good behavior, but still has to complete 1,000 hours of community service. He’s also on probation for five years. The disgraced CBS News producer is searching for a new job.

Halderman’s lawyer told “Entertainment Tonight” his client is looking to return to TV. "Yes that's his strength and [in] his field there are plenty of people who have had rocks in the road and got past it and went on to lead [a] meaningful life, and I expect that will happen in his life." (Perhaps he could get his start with an appearance on Letterman’s “Stupid Human Tricks.”)

The New York Post reports that a source close to Halderman says the ex-con has received an assignment from a leading men's magazine to write a first-person account of his short stint behind bars.

Dave didn’t joke about Halderman’s release, but “Late Late Show” host Craig Ferguson did: “The guy that tried to destroy David Letterman was let out of prison today. I was like, ‘Really? Jay Leno was in prison?’”

Total views: 47232