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David Letterman has been praised for his talk show The Late Show With David Letterman, which ran for 22 seasons on CBS from 1993-2015. But, in 2009, Letterman’s career was jeopardized when he was blackmailed for $2 million.
Letterman received an envelope from his driver marked “Privileged and Confidential.” The comedian would open the envelope containing a multitude of documents, including “Treatment for a Screenplay,” which was a threat to ruin Letterman if he did not comply and pay the money.
Now, who gave the envelope to Lettermans’ driver? A former CBS News producer, Robert “Joe” Halderman. After admitting guilt, Halderman said, “I knew throughout this time that I was not engaged in a legitimate business transaction with Mr. Letterman and that what I was doing was against New York law.”
He continues, “I understand that my attempt to extort $2 million from Mr. Letterman violated his and his family’s privacy. I promise to respect their privacy in the future.”
Why Was Robert “Joe” Halderman Blackmailing David Letterman?
Halderman, an Emmy Award-winning producer, admitted to guilt, saying he was trying to extort $2 million from Letterman and, in return, would keep quiet about the host’s affairs.
In a statement, Halderman said, “On the morning of September 9, 2009, I gave a sealed envelope to Mr. Letterman’s driver as he waited outside of Mr. Letterman’s Manhattan home,” Halderman said in the statement, called an allocution. “I asked the driver to give the envelope marked ‘Privileged and Confidential’ to Mr. Letterman.”
Furthermore, Halderman met with Letterman’s lawyer—Jim Jackoway—three separate times later that month. And in October, Halderman said, “I deposited a check for $2 million that Mr. Jackoway gave me.”
After depositing the check into a Connecticut band account, the next day, Halderman was arrested. The then-District Attorney Morgenthau set his bail at $200,000, and Halderman was released.
What Were Robert “Joe” Halderman’s Charges?
Halderman had initially pleaded not guilty to grand larceny charges and was facing a 15-year prison sentence. But he eventually entered into a plea deal. The deal included: serving six months in prison, four and a half years probation, and 1,000 hours of community service, 500 of which will be served in a Connecticut homeless shelter.
Halderman had first claimed he only wanted to sell Letterman a screenplay, which included deplorable details of the comedian’s life.
The Manhattan district attorney’s office said, “Halderman allegedly threatened to reveal “personal and private information” if Letterman did not accede to his demands to purchase the one-page screenplay.”
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In a statement, Halderman said, “I apologize to Mr. Letterman and his family, Stephanie Birkitt [one of the women Halderman said had engaged in a sexual relationship with Letterman] and her family, and certainly to my friends and family.”
He ended it with, “I feel great remorse for what I’ve done.”
Birkitt, one of the alleged women, was a one-time personal assistant to Letterman and had lived with Halderman as his girlfriend from August 2005 to August 2009.
What Was David Letterman’s Response to Being Blackmailed?
Letterman made a statement on his talk show announcing the blackmail and admitted to affairs with female staffers.
On the show, when Letterman announced the blackmail scheme, he said he decided to go public with his affairs after receiving a package left on the back seat of his car demanding money to keep his infidelities a secret.
He continued by telling the audience what the letter said, “I know that you do some terrible things, and I can prove that you do these terrible things … and sure enough, what was contained in the package was proof that I do terrible, terrible things.”
He admitted to not just having a one-time romantic affair with one member but staff but to having “sex with women who work with me on this show.”
Letterman also explained how he called his attorney to meet with the blackmailer. His lawyer then contacted New York prosecutors to catch Halderman.
The late-night comic explained, on air, how his attorney contacted New York prosecutors to catch Halderman. Letterman later testified before a grand jury.
When Halderman was sentenced, Letterman didn’t attend. But, he wrote a statement and had his lawyer read it, “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.”
He continues, “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.”
