On Thursday, “Daily Show” host Jon Stewart revealed his least favorite guests from the show. These experiences continue to haunt him.
The guests he identified were pivotal in the lead-up to the 2003 invasion of Iraq and the subsequent conflict: Then-Defense Secretary Donald Rumsfeld and then-New York Times reporter Judith Miller, who was instrumental in promoting the administration’s war-related claims.
Stewart focused specifically on Rumsfeld in the “After The Cut” segment.
Rumsfeld was a guest in 2011 to promote his book, prompting Stewart to prepare extensively, akin to “cramming for an exam.”
Stewart explained his plan: “I worked out a logic trap. 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.”
However, the interview was disrupted almost immediately.
When Stewart mentioned the administration “selling the war,” Rumsfeld countered with “making the case,” leading to a debate over terminology.
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It was at this moment that Stewart realized his strategy had faltered.
“That whole interview lived in the space between ‘selling’ and ‘making a case,’” Stewart observed. “That’s where the whole thing was. But I was so in my head that I let that opening slip and did not, to my feeling, have a satisfying encounter with him. And it tortured me.”
Stewart admitted he struggled to sleep after the interview.
“I lost more sleep over that interview than he lost over the entire war,” he remarked.
The situation worsened after the show.
“And here’s what that motherfucker did afterwards that was the knife in the fucking ―” Stewart said, miming a stabbing gesture. “He sends me a note afterward because he knew what I was trying. He sends me a note afterward 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.’”
Stewart dramatically mimed thrusting a knife deeply.
The interview with Rumsfeld has lingered in Stewart’s memory, resurfacing in 2015 when he described it as a “shitty” interview, although he kept things in perspective.
“It’s still just an interview,” Stewart said then. “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 passed away in 2021 at the age of 88.
