Why Jon Stewart failed to make John Yoo squirm.

Former Bush administration lawyer John Yoo

How did he do it? It’s a question John Yoo has been getting a lot lately. How did he manage to outwit Jon Stewart? (“He slipped through my fingers,” Stewart recalled after Yoo’s recent appearance on The Daily Show. “It was like interviewing sand.”) Easy, says Yoo. “I’ve spent my whole career learning to settle down unruly college students who have not done the reading.”

Yoo reflected on his Daily Show experience Friday during a luncheon in Washington hosted by the Federalist Society—as friendly an audience as Stewart’s was unfriendly—pegged to the release of his new book, Crisis and Command, about executive power throughout American history. He came to talk about presidential power and how the best presidents have been the ones willing to make bold decisions without congressional approval. But all anyone wants to know about is what it’s like to be on the Daily Show. He said: “Despite three books and I don’t know how many journal articles, it’s the only thing I’ve done that’s ever gotten the notice of my students.”

Opponents of the Bush administration’s use of torture had high expectations for Monday’s interview. Finally, Stewart would take the same razor to Yoo that had so memorably eviscerated the likes of Tucker Carlson, Chris Matthews, Jim Cramer, and Betsy McCaughey. The Orwellian logic that undergirded the “torture memos” would collapse once and for all. The punishment would be so cruel, so unusual, Yoo would beg for water-boarding.

Not quite. The interview was an exercise in frustration. Stewart didn’t come at Yoo with gotcha questions, as Yoo’s critics might have liked. Instead, he asked open-ended ones—”Are you a good lawyer?”—presumably intended to give Yoo enough rope to hang himself. Instead, Yoo was swinging from it. Yoo didn’t dodge questions so much as reframe them, answer them in an extremely friendly and civil way, and—insult to injury—tack on a joke at the end to show he’s a good sport. Stewart actually took a commercial break for relief. Oh, also: “I didn’t prepare at all,” Yoo told me on Friday.

Stewart’s performance was widely deemed a failure. He was too conciliatory. He didn’t ask about whether torture works or not. He didn’t correct Yoo on his factual fudging, such as his claim that Abu Zubayda was a No. 3 leader of al-Qaeda, nor did he challenge him on whether interrogators had crossed the line between harsh interrogation and torture. Stewart himself later apologized for not “nailing” Yoo.

But was “nailing” him ever a possibility? Yoo has slipped the grasp of many critics through the years. Part of the reason is his demeanor: calm, good-humored, endlessly patient. It throws people, especially those expecting a younger, Korean Dick Cheney.

But it’s also Yoo’s rhetorical skill. Stewart failed to “nail” Yoo not because he wasn’t prepared. (Although perhaps Stewart could have quoted some of the harsher memos.) He failed because Yoo is a lawyer. The chief criticism against Yoo is that, as deputy assistant attorney general for the Office of Legal Counsel after 9/11, he gave the Bush administration legal cover to torture suspected terrorists. In a time of war, he wrote in what became known as the “torture memos,” the president has expanded power to make decisions without congressional approval. When it comes to what’s torture and what’s not, he wrote, only treatment that inflicts suffering equivalent to organ failure “or even death” constitutes torture. In later interviews, he suggested that nothing—no law and no treaty—could stop the president from ordering torture if the circumstances required it.

Yoo wasn’t advocating these techniques, he can say. He was simply answering the question of whether the Constitution allows the president to make these decisions in a time of war. Even if his interpretation of the law led to the use of these techniques, that was the decision of the person ordering them—not the person who interpreted the law as allowing them.

It’s the difference between law and policy, he said. In a brief interview before his speech, I asked him if he thought some of the methods interrogators used after 9/11 crossed the line between harsh interrogation and torture. “I really don’t know,” he said. “It all depends on the circumstances.” Lawyers are not hired to say what to do in this or that situation, he said. “That’s up to the people who know all the facts.”

And that’s why Stewart was set up to fail. No matter what the question, Yoo was able to fall back on vagaries about constitutional interpretation, war and peace, and presidential power. Your beef isn’t with me, he seemed to say. It’s with the Founding Fathers. They left the powers of the presidency deliberately vague in order to give the president wiggle room, which the greatest presidents—Lincoln, FDR—have seized. Plenty of scholars dispute this view of the presidency. And Yoo’s view of history may well be oversimplified, as Jeffrey Rosen argued on a panel with Yoo on Thursday: Lincoln didn’t consult Congress before declaring war against the South, for example, but he did afterward.

Stewart could have raised similar points. But those aren’t damning witticisms. They’re nuanced arguments, to which the most likely reaction would be “Hmm, that sounds sensible.” Stewart is effective when his opponent is making a foolish point, not when he has an unorthodox constitutional interpretation. Which is why Stewart wasn’t going to pin Yoo down—even if he had done all the reading.