From The Independent:

ONE morning in December 1824, the Duke of Wellington received an unpleasant letter. 'My Lord Duke,' it began, 'in Harriette Wilson's Memoirs, which I am about to publish, are various anecdotes of Your Grace which it would be most desirable to withhold, at least such is my opinion. I have stopped the Press for the moment, but as the publication will take place next week, little delay can necessarily take place.'

The letter, signed by one Joseph Stockdale, a pornographer and scandal-monger, was a naked attempt at blackmail. The Duke was a field marshal, cabinet minister, national hero, husband and father, while Harriette Wilson was a famous London courtesan past her prime, then living in exile in Paris. Wellington was being asked to pay money to be left out of her memoirs.

His response is famous: 'Publish and be damned!'

If David Letterman's lady friend staffer had threatened to sue for sexual harassment, but her lawyer told Letterman's lawyer that she'd be willing to sign an agreement promising never to say a word about the affair in return for a $2 million settlement, that would be perfectly legal, right?I mean the law encourages people to threaten to sue their bosses for sexual harassment, right? And the law also encourages the parties to settle out of court, and promises of secrecy in return for money are legally enforceable, right?

Is the difference in the Letterman deal that a nosy third party is involved? Fair enough, but that doesn't seem to be the principle involved in the Bill Cosby case.

This David Letterman case reminds me of the 1990s Bill Cosby case in which a woman was convicted and sentenced to five years in jail for asking Bill Cosby for money in return for not selling her story to a supermarket tabloid that she was (at least according to her mother) Cosby's daughter.

When Autumn Jackson got sent off to prison for five years, CNN reported:

The judge in the case ruled that Cosby's alleged paternity was irrelevant and that the real issue was whether the defendants committed extortion. Cosby testified he had sex once with Jackson's mother but denied being her father.

A 1997 NYT article explained:

At one point during closing arguments, Mr. Baum told the jury: ''Autumn Jackson had a right to sell her story. Autumn Jackson had a right to ask her father to negotiate a settlement of her rights. ''Two rights don't make a wrong,'' he added.

But prosecutors say that two rights do make a wrong, when they constitute a threat to harm someone's reputation, accompanied by a demand for money. The disagreement highlights an age-old legal debate about what one lawyer calls the paradox of extortion and blackmail (the terms are often used interchangeably).

''The reason blackmail has exerted fascination for scholars is that it's a profoundly mysterious offense,'' said Leo Katz, professor at the University of Pennsylvania Law School and author of the book, ''Ill-Gotten Gains: Evasion, Blackmail, Fraud, and Kindred Puzzles of the Law.''

''What makes it mysterious is that you are threatening to do something which you are perfectly entitled to do, and you are asking for a benefit in return for not doing it,'' he said.

James Lindgren, a law professor at Northwestern University who has written extensively on blackmail and extortion, said: ''It's hard to see when you're doing things that individually are not wrong. It's not wrong to go to the tabloids, not wrong to make public claims about someone being your father, not wrong to ask for money.

''What's wrong,'' he said, ''is when you use the explicit leverage of public disgrace to get what you want.''

Some economists and lawyers have debated why blackmail and extortion are crimes in the first place. Paul Shechtman, a former top Federal prosecutor in Manhattan who performed an economic analysis of blackmail with Douglas H. Ginsburg, now a Federal Court of Appeals judge, found an economic rationale for keeping it a crime. Legalizing blackmail, he said, would spawn an entire industry that would dredge up secrets to conceal again for a price.

''As a general matter, it's not in anybody's economic interest to have people dig up dirt and rebury it,'' Mr. Shechtman said.

In any case, the extortion and blackmail riddle has not given prosecutors much pause. ''Prosecutors have been prosecuting, blissfully ignorant of the debate,'' Mr. Shechtman said. And they have been winning convictions as well.

Let's say your dad is, I don't know, Barack Obama, and a book agent tells you that he could get you a $2 million book deal for the story of your life. You'd like $2 million, but you'd rather not have all the publicity, and you would rather not cause your father, whom you voted for, any political damage (especially if, say, your mom, Natasha Gromyko, was your dad's KGB controller operating out of the Soviet Mission to the UN in 1984, and you'd just as soon not open that whole can of worms. I mean, like, the Cold War is so over.) So, wouldn't it be better for both you and your dad if you came to some quiet agreement where in return for $2 million you'd agree to never tell?

How about, instead, if you were thinking about writing a book entitled, My Dad, Barack Obama, and he got wind of it and called you and offered you $2 million not to finish it? That's legal, right?

How about if you sent him a birthday card mentioning you were thinking about writing your autobiography (precocious autobiographical tomes run in the family!) and he called back and offered $2 million if you wouldn't publish it? That's legal, isn't it?

How about if you called him and told him your plans to write a book, and then said, "But, I'm thinking about a number ..." And then he said, "Let me guess, two million dollars." And then you said, "Dad, you can read my mind!" Is that legal?

What if you weren't thinking about writing a memoir at all, but one day in December 2007, Valerie Jarrett knocks on your door with a satchel of cash and a contract to never write your memoirs. Is that legal?

Kind of seems like the law is "Don't mess with popular celebrities."

Or maybe it's just that the law frowns on people who try to cut out the lawyer middlemen and deal directly with their opposite numbers.