Old School. Biblically Independent.
By Dustin Rowles | TV | August 14, 2026
In last night’s Pajiba Love, Mike led with Jon Stewart’s regret over his interview with John Fetterman a couple of weeks ago, and I — like Mike — do not think he has anything to regret. The man is a United States Senator, and there is no need to go easy on him because he suffered a stroke. No one took it easy on Uncle Joe for his health issues. That said, I don’t know why Mike had to get Maine involved! We’re doing great! We got a new guy who is polling better against Susan Collins that the old guy!
Anyway, Comedy Central surfaced one of those behind-the-scenes clips from The Daily Show this week (via The AVClub), where an audience member asked him what his worst interview was. Stewart, who opposed the Iraq War from the beginning, mentioned two people: Judith Miller, the NYTimes reporter who ginned up evidence of WMDs that helped get us involved in the war in the first place was one, but that interview that really stuck in his craw was the one with former Secretary of Defense, Donald Rumsfeld. I remember that interview, and while I didn’t remember it as a failure, exactly, Stewart felt like Rumsfeld got the better of him.
Basically, what happened is that Stewart read Rumsfeld’s book, studied it cover-to-cover, dog-eared pages, and “worked out a logic trap that was a elaborate.” He was convinced he was going to “win” that interview. Unfortunately, he got off on the wrong foot, and before he could set the trap, he got into a disagreement with Rumsfeld. Stewart claimed that the Administration was “selling the war,” while Rumsfeld maintained that they were “making the case.” And instead of ultimately laying his trap and ensnaring him, the “whole interview lived in the space between selling and making a case. That’s where the whole f***ing thing was. 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. It tortured me. Like, literally, couldn’t sleep. And I realized … I lost more sleep over that interview than he lost over the entire war.”
But that’s not all. After the interview, Rumsfeld twisted the knife into his back. That “mother******” sent him a note, and the note read, “Jon, really enjoyed the interview. I wish I had known you when we were younger. I bet we would have been friends.”
If y’all remember how much Jon Stewart loathed the Iraq War and the architects of it, you’ll understand just how much that burned.
