Most Supreme Court arguments last one hour-30 minutes for each side. At unpredictable intervals, however, the Court grants one party several extra millennia of agony as a once-solid case disintegrates in full view of the entire courtroom.

This happened Wednesday in the argument in United States v. Alvarez, the much-discussed Stolen Valor Act case. The victim of the agony extension was Jonathan D. Libby, deputy federal public defender from Los Angeles. His client, Xavier Alvarez, is a habitual liar who has regularly and vainly tried to convince people that he is a former U.S. Marine, an old-timer with the Detroit Red Wings, the ex-husband of a Mexican movie star, the personal rescuer of the U.S. Ambassador to Iran-and, unfortunately for him, a recipient of the Congressional Medal of Honor. That latter claim violated the Act, passed in 2005. It makes it a federal crime for anyone to "falsely represent[] himself or herself . . . verbally or in writing, to have been awarded" any military decoration by the U.S. military.

So the issue was: Can the U.S. government make it an offense to tell a lie about one's own military career, even if the speaker doesn't use the lie in an attempt to defraud others or gain some kind of employment or other advantage?

All was normal as Solicitor General Donald Verrilli made the government's case. There is no value in deliberate, knowing, false statements of fact, he argued. The government has an interest in preventing phonies like Alvarez from demeaning military decorations by claiming to have won them. The speech is targeted narrowly, at knowing lies about a few medals. As long as a statute like the Act gives adequate "breathing room" for protected speech-satire, parody, fiction, political hyperbole, etc.-the government can ban it.

But when Libby rose to speak for Alvarez, a rip appeared in the space-time continuum. Chief Justice John Roberts asked Libby, "What is the First Amendment value in a lie, pure lie?"

It's the obvious question, and there's an answer; indeed, by an earlier question to Verrilli, Justice Anthony Kennedy had furnished the opening line. There may be no value in a lie, it might have begun, but there is tremendous value in freedom to lie without worrying about being arrested. As Justice Kennedy said earlier, we don't want a Ministry of Truth monitoring what we say to each other. Freedom of speech means the freedom to misuse speech-unless that speech falls under one of a number of narrow "historical exceptions" laid out by this Court over the years: defamation, fraud, incitement to violence, criminal solicitation, etc. Less than two years ago, in a case called United States v. Stevens, this Court warned the government not to try to invent new exceptions. But that's just what they've done here.

Libby went a different way.

"There is the value of personal autonomy," he said.

"The value of what?" Roberts asked.

"When we create our own persona, we're often making up things about ourselves that we want people to think about us, and that can be valuable. Samuel Clemens creating Mark Twain. That was creating a persona, and he made things up about himself…"

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Mark Twain? Alvarez is Mark Twain?

Libby never really got out of that one. Defending lying is a lot harder than defending freedom. Libby was soon asked whether his principle would also require voiding the long-standing prohibition of wearing false medals (unlike the Act, which criminalizes merely claiming to have won them). What about the effect on perjury statutes? Or on prohibitions on false statements to government officials?

Justice Elena Kagan asked: "Let's suppose that I agree with [statements in earlier cases] that there is no constitutional value in a false statement of fact, and the reason why we protect some false statements of fact is to protect truthful speech...What truthful speech will this statute chill?"

"Your Honor," Libby said, "it's not that it may necessarily chill any truthful speech."

Kagan responded, "[T]hat's a big concession, Mr. Libby."

The big Court clock by now seemed frozen, as if the chamber had become the appellate tribunal of Dante's Hell.

Handicapping oral argument is chancy, but in addition to Roberts, Justices Antonin Scalia and Samuel Alito seemed to agree that allowing people to claim medal-winner status damages the government. Justice Anthony Kennedy, the closest thing this Court has to a First Amendment absolutist, began the argument with a standard critique of the Act. "To say that the cases you mentioned say that there is no value to false speech, I simply cannot agree with that broad proposition," he challenged Verrilli. "They do [say that] in the particular context of a recognized tort like intentional infliction of emotional distress."

But soon he was musing aloud about an alternative way he might just be able to hold for the government. "[Y]ou can argue that this is something like a-a trademark, a medal in which the government and the armed forces have a particular interest, and we could carve out a narrow exception for that," he said, channeling the amicus brief of the Intellectual Property Amicus Brief Clinic of the University of New Hampshire School of Law (which I wrote about last week). Later, he returned to that theme: "it seems to me your best analogy is the trademark analogy, Olympic case, et cetera."

Justice Stephen Breyer, as is his custom in First Amendment cases, danced all over the lot. (At one point he asked whether the government could penalize a false answer to the question, "Are you hiding Jews in the cellar?") But he too seemed interested in the intellectual property approach. "[W]e're willing to protect the Olympics Committee when a false person saying he's the Olympics Committee might deprive the Olympics Committee of a penny, while here they are saying that to win this great medal, say the Congressional Medal of Honor, the highest award in the military the nation can give, you're deserving of the most possible, grandest possible respect, and we don't even want you to have to think about somebody having taken that name falsely, and so we will just criminalize it to discourage such activity that undermines the very thought and purpose of giving the medal."

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Suddenly, 6-3 seemed like a possibility.

Justice Sonia Sotomayor spoke up for a more traditional view of the First Amendment. "Justice Story many, many years ago said, look, falsehoods have no value as such, but the 'breathing space' concept is defined by those falsehoods which cause injury to rights that people possess, to-to pecuniary interests that they have, or to the reputation of others," she told Verrilli. "And almost every statute where we have approved . . . has affected one of those three things. So please tell me what's wrong with Justice Story's view."

Verrilli replied there is a fourth category, allowing punishment of speech that harms the government's "systemic interests." As for the limit of that principle, neither Verrilli nor anyone else spelled out a very convincing one.

For example, could the government criminalize intimate lies? Sotomayor asked Verrilli whether the government could outlaw padding a resume to a potential mate. "I take offense when someone I'm dating makes a claim that's not true," she said.

"As the father of a 20-year-old daughter, so do I," Verrilli responded.

And Justice Kagan asked a question that must have made the courtroom seem even more like hell to some of the crowd. "The government has a strong interest in the sanctity of the family, the stability of the family, so we're going to prevent everybody from telling lies about their extramarital affairs."

Verrilli bobbed and weaved for a minute, but finally answered: "That's a hard case."