Robert "Joe" Halderman will be sent to jail for allegedly trying to extort $2 million from Letterman after learning his girlfriend was sleeping with the Late Show host.
After Halderman's arrest, Letterman shocked his TV audience by revealing both the blackmail and the fact that he'd slept with unnamed female employees.
Halderman had said he just offered Letterman a chance to buy -- and keep private -- a thinly-veiled screenplay about his life.
Halderman had also told the comedian's lawyer he would keep copies of his information on Letterman's love life for "protection," worrying that he could be fired - or even killed - in retaliation for the scheme, Manhattan prosecutors said in court papers.
"The issue is your client does not want this information public," Halderman told Letterman's attorney in a secretly taped conversation, according to prosecutors. "I have said, for a price, I will sign a confidentiality agreement and I will not make this information public. That's, that's the deal."
"Should I be fired, mysteriously ... if my house burns down ... any number of things that, I don't know this person, I've never met this person, I have no idea who or what he is or is capable of," Halderman said, according to the court papers. He added that someone might decide "the only way to be sure that I never talk to anybody is for somebody to kill me," the papers said. Prosecutors arranged for Letterman's lawyer to record two meetings with Halderman.
Halderman laid out his cover story frankly, saying he would tell his accountant, "I'm optioning a screenplay. I think that's how we should define it," according to the papers.
Still, he expressed misgivings about the scheme, telling Letterman's lawyer he was "not terribly impressed by" his own conduct, according to the papers.
"His efforts to define and characterize his actions as something legitimate and make the 'deal' appear normal are nothing more than a transparent charade," assistant district attorneys Judy Salwen and Peirce R. Moser wrote.
Halderman's lawyer, Gerald Shargel, stood by his contention that the exchange was aboveboard business.
"He had intellectual property relating to Letterman's poor conduct. He had the right to sell that intellectual property," Shargel said Tuesday.
Halderman has said in court papers that he threatened nothing more than a sale to someone else if Letterman said no.
In a package given to Letterman's driver Sept. 9, Halderman said he needed "a large chunk of money" and described a screenplay depicting Letterman's life unraveling after his personal life was exposed, authorities said.
The package included photos, personal letters and portions of a diary in which Halderman's ex-girlfriend - a Letterman assistant - described an affair with the comic, law enforcement officials have said.
Halderman referred to letters, phone bills and the woman's "confession" in the taped conversations, according to court papers.
"There was no extortion. There was no extortion here involved," Shargel said.
"I have had sex with women who work for me on the show," Letterman told his audience on the Oct. 1 taping.
The 52-year-old Halderman faced up to 15 years in prison if convicted.
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