Robert "Joe" Halderman thought he had a $2 million secret and a surefire plan to cash in on it: Pay him, or he'd ravage David Letterman's congenial, clean-cut image by revealing the late-night TV icon's office affairs.
Instead, Halderman ravaged his own life. The former producer for CBS' "48 Hours Mystery" is expected to start a six-month jail term Tuesday after admitting in March to the shakedown attempt.
Letterman blunted the blackmail threat by divulging his workplace dalliances himself. His viewership hasn't suffered, and his status was barely scuffed.
But celebrity lawyers and image-makers say it's unclear whether the case will function as a cautionary tale that deters similar episodes.
Many luminaries would rather beat back or settle such matters privately than press charges that would air their dirty laundry, the experts say. Even if a threatened celebrity is willing to go public, few have the persona and forum to do it the way Letterman did: in a forthright, sometimes funny monologue on his own show.
"There are lots of people running around the planet thinking that blackmailing celebrities or prominent, wealthy people is a great way to make a living," said veteran celebrity publicist Michael Levine. "The lesson of Letterman is: Every so often, you're going to run into someone who isn't going to play."
But, he added, "Not all people are David Letterman."
Stars ranging from Cameron Diaz to Yoko Ono have been confronted in recent years with people demanding money to keep photos or information private. Those are episodes that became criminal cases and public knowledge. Many others are kept from ever becoming known, attorneys say.
Los Angeles lawyer Mark Geragos said he has discreetly dealt with such situations for notable clients he won't name, including several he handled after the Letterman episode.
"Most entertainers are loath to go public with these things if they can at all help it," Geragos said.
Halderman, 52, isn't expected to speak at his sentencing and declined through his lawyer to be interviewed. Halderman's expected jail term and 1,000 hours of community service were set when he pleaded guilty to attempted grand larceny.
He admitted in court that he tried to squeeze $2 million from the "Late Show" host "by threatening to disclose personal and private information about him, whether true or false."
He presented the threat as a faintly fictionalized screenplay about Letterman — and backed it up with information authorities have said Halderman gleaned from reading his former girlfriend's diary. She worked for Letterman and described an affair with him in the diary, authorities have said.
Halderman's plea deal requires him never to discuss the material.
Letterman revealed on-air Oct. 1 that he'd had sex with women who work for him and disclosed the blackmail attempt. It was the first the public had heard of the case — prosecutors announced the charges the next day — and made it a story told largely in Letterman's voice. Critics and public-relations experts hailed his disclosure as a master stroke.
"Letterman gave everybody, within what's reasonable, what they needed to know to make up their own minds and decide what's right and wrong," said Winston-Salem, N.C.-based crisis-management consultant Rick Amme.
The case appears to have made little difference with television viewers. Letterman is averaging 4 million viewers this season, up 3 percent over last season, according to the Nielsen Co. He was helped by not having to compete against Jay Leno for several months.
Still, Letterman has said the scandal took a personal toll.
"You take a look at the explosion, and it knocks you down, and you wake up every morning, and you're scared and you're depressed and sad," the comic said Friday on "Live! With Regis and Kelly."
"And you kind of got to let that knock you down and knock you down, and then pretty soon you've got to start knocking IT down," Letterman added.
Letterman isn't expected to attend Halderman's sentencing.
Halderman no longer has his job with CBS' "48 Hours Mystery." The network also hosts Letterman's show.
After getting out of jail, he's expected to do his community service at New York and Connecticut organizations that provide job training to formerly homeless people and convicts getting out of prison.