Moral-reasoning pop quiz: There’s a film coming out—a thinly disguised portrayal of a media mogul—and word is that if it’s released it will hurt the mogul’s reputation. Powerful people intervene: they call a meeting and offer the movie studio money—eight hundred and forty-two thousand dollars—to scrap the movie and destroy the negatives. Would it be wrong for the studio to take the money? “It’s an interesting question,” James Lindgren, a law professor at Northwestern, said last week. The mogul in question was William Randolph Hearst, and the movie was Orson Welles’s “Citizen Kane.” The studio turned down the offer, but, Lindgren asked, “had they given in and taken the money, could the studio have been prosecuted for extortion?”

David Letterman Illustration by Tom Bachtell

Lindgren was on the topic because of another inflammatory film proposal—the one about the talk-show host who has affairs with female staff members (the one that the CBS producer Robert Joel Halderman allegedly left, last month, with David Letterman’s limo driver). Halderman, as everyone knows, is being prosecuted for attempted grand larceny (he has denied wrongdoing), but the act he is accused of committing is blackmail, a crime that, in philosophical and legal circles, presents a conundrum. Lindgren is the author of a paper called “Unraveling the Paradox of Blackmail,” which raises the question: why is blackmail considered a crime? The thinking goes like this: It’s perfectly legal for Halderman to write, or threaten to write, a screenplay (or an e-mail to TMZ) exposing the fact that David Letterman had flings with “Late Show” employees. It’s also legal for Halderman to ask Letterman for money as part of a business transaction. So why are the two things illegal when you put them together? In other words, Lindgren said, “Why is it illegal to threaten to do what you can do legally anyway?”

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Most theorists agree that blackmail should be illegal; they just can’t agree on why. A few days after Letterman’s confession, Saul Smilansky, the author of “Ten Moral Paradoxes,” said that, in his opinion, what Halderman did wasn’t heinous. “It’s not terribly attractive, but it’s still fairly standard capitalist practice,” he said. “The Marxists used to say that capitalism is like blackmail—everyone tries to buy people off. Many social transactions look like blackmail when you examine them.” He listed a few: “couples in divorce proceedings basically blackmailing each other to get a better deal,” consumers telling a company “if they don’t get a settlement they’ll go to the press”—in other words, any negotiations based on threats. What makes blackmail different? “There’s no good reason to allow it,” Smilansky said. “But our attitude towards blackmail, that it’s so unusual, so terrible—it’s just sanctimonious.”

Richard Epstein, the University of Chicago and N.Y.U. law professor, said, “There’s this terrible fear of monopoly power. Halderman is sort of a local monopolist.” To show that he shouldn’t be allowed to “put the squeeze on the guy,” Epstein said, “you have to prove that a world where blackmail is illegal is a better place.” Epstein is the author of an essay called “Blackmail, Inc.,” in which he describes what it would be like if blackmail were legal and were handled by big corporations. In that scenario, Epstein said, Halderman would have hired Blackmail, Inc. “So Blackmail, Inc., goes to Letterman, and they say, ‘Look, this is going to really bust your chops if this gets out, but we’re going to help you keep it a secret. So the company puts out false public information designed to throw people off the scent.” The problem, he said, is that blackmail leads to fraud: “You lie to the world. And lying to the world is wrong.”

Other experts addressed the ick factor. “It has something to do with the truth about human psychology,” Mitchell Berman, a legal theorist at the University of Texas, said. “There’s an anti-commodification norm” (meaning that people aren’t O.K. with there being a market for some things; he mentioned prostitution). Lindgren imagined a cash-free, and legal, scenario: “If Halderman had said, ‘Stop doing this or I’ll expose you,’ and Letterman said, ‘I don’t want to stop doing this,’ and Halderman had said, ‘I’m forcing you to stop doing this or I’ll ruin your reputation’—that would probably not have been blackmail.” The Harvard law professor Steven Shavell, who calls himself a “quasi Letterman fan,” said the issue lay with Halderman’s motives: it’s about “hurting the person who committed the crime.” He suggested that Halderman’s attempt was wrong for the same reasons that vigilante justice is wrong, and he downplayed the idea of a “blackmail paradox,” calling such a notion “a toy of philosophically oriented academics.”

A final call went out to Walter Block, the libertarian economist. Block believes that blackmail, like smoking, is “yucky” but should be legal. “He only threatened to be a gossip—maybe a screenwriter,” he said of Halderman. “Screenwriting and gossiping are legal. If it’s legal to do it, it should be legal to threaten to do it.” Of Halderman’s defense team, he said, “If the purpose is to promote justice, they should argue that it’s an unjust law, and he should get off free.” Of his fellow ethics experts, he said, “They wouldn’t know just law if it bit them in the rear end.” ♦