Fine Line of Distinction Between Extortion and a Payoff

Scenario #1: A man contacts a married multimillionaire TV personality and allegedly threatens to spill the beans about the celebrity's sexual peccadillos if he doesn't pay him to stay silent.

Scenario #2: A woman who is reported to have had a sexual affair with a married billionaire sports personality schedules a press conference to discuss the reports, only to cancel abruptly amid rumors that she and the man are negotiating a payoff that will keep her silent.

The first scenario involves a man named Robert J. "Joe" Halderman, who prosecutors in New York say demanded money to remain silent about David Letterman's sexual affairs with staffers, and who claims he was merely trying to sell the "Late Night" host a screenplay for $2 million.

The second scenario involves a brunette named Rachel Uchitel, whose reported affair with Tiger Woods was revealed in the National Enquirer days before the golf legend crashed his car, leading to his admission to "transgressions." Uchitel canceled her scheduled press conference Thursday amid rumors that she was negotiating a settlement with Woods to keep her mouth shut.

One allegedly involves extortion. Halderman is charged with attempted first-degree grand larceny and could face jail time if convicted.

The other is perfectly legal.

Judge Andrew Napolitano, Fox News' senior legal analyst, said the situations differ in that the first scenario is involuntary on Letterman's part and was done under a threat allegedly initiated by Halderman. But the second scenario, if true, is a voluntary act on Woods' part and was performed without a threat from Uchitel.

Asked why he thought Uchitel's press conference was canceled, Napolitano told Fox News' Shepard Smith that the credit likely should go to Uchitel's lawyer, Gloria Allred. "I think that Gloria is probably negotiating -- I'll give her credit -- with Tiger's lawyers for a significant sum for her client and for her fee.

"Gloria is one of the most media-savvy lawyers in California ... She would not cancel the news conference at the height of this crisis, which everyone would be watching, unless it was in her client's best interest to do so."

Napolitano also noted that it would be financially beneficial to Uchitel to continue her initial claims that she and Woods never had an affair.

"I wonder if any money would be involved to maintain that storyline," Napolitano said. "One of the reasons [Woods is] worth a billion is because he's Mr. Clean, and the biggest marketers in the country have hired him to represent their products. They might not want him representing those products if it turns out he's not as Mr. Clean as he's represented himself to be."

Allred, when asked why Thursday's news conference was canceled, declined to comment to FoxNews.com. She also declined to comment regarding reports that Woods and Uchitel spoke as recently as late Wednesday, possibly to discuss financial arrangements.