“Daily Show” host Jon Stewart on Thursday named his least favorite guests on “The Daily Show.”
And one of those segments has truly haunted him.
Both of Stewart’s least favorite guests who came to mind first were involved in setting the stage for the 2003 invasion of Iraq and the war and occupation that followed: Then-Defense Secretary Donald Rumsfeld and then-New York Times reporter Judith Miller, who helped the administration push the claims that led to the war.
But it was Rumsfeld he focused on for the “After The Cut” segment.
Rumsfeld appeared on the show in 2011 to promote his book, and Stewart said he stayed up all night studying it, as if he were “cramming for an exam.”
“I worked out a logic trap,” Stewart said. “It was a labyrinth, and I was going to draw him into my trap and then I was going to spring it. I was going to win the Iraq War. I was going to win the interview.”
Instead, the interview was derailed in the first minute.
Stewart referred to the administration “selling the war,” but Rumsfeld interrupted him to say “making the case” instead ― and the two ended up debating the two terms.
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That’s when Stewart realized he was no longer setting his trap.
“That whole interview lived in the space between ‘selling’ and ‘making a case,’” he said. “That’s where the whole fucking thing was. But I was so in my head that I let that opening slip and I did not, to my feeling, have a satisfying encounter with him. And it tortured me.”
He said he literally couldn’t sleep afterward.
“I lost more sleep over that interview than he lost over the entire war,” he said.
But the encounter didn’t end there. In fact, it actually got worse.
“And here’s what that motherfucker did afterwards that was the knife in the fucking ―” he said as he mimed a stabbing gesture. “He sends me a note afterwards because he knew what I was trying. He sends me a note afterwards and he goes, ‘Jon, really enjoyed the interview. I wish I had known you when we were younger. I bet we would have been friends.’”
With that, Stewart dramatically mimed sticking a knife in deep.
The Rumsfeld interview has truly haunted Stewart, as he’s brought it up before. In 2015 ― four years after the encounter ― he called it a “shitty” interview, but also kept it in perspective.
“It’s still just an interview,” he said at the time. “He’s the one who has to live with the repercussions of what he really did, so there’s nothing that could happen on my show that carries that same level of regret.”
Rumsfeld died in 2021 at the age of 88.