Even by the standards of flippant Nazi analogies, Comedy Central’s Jon Stewart had an especially ill-timed Nazi comparison on Wednesday as he taped The Weekly Show podcast before Charlie Kirk’s assassination and ahead of its Thursday release. According to Stewart, President Trump sending ICE to Chicago can be roughly analogized with Nazi invasions in World War II.
Stewart began, “It is, we're taping this on Wednesday, September 10th, it's gonna be airing tomorrow, and today is the day they launched Operation Midway Blitz. Named for the city of Chicago and what the Nazis did through Europe. What could go wrong?”
“Blitz” just means lightning. Has Stewart ever watched a football game where the defense blitzes the quarterback? The Seattle Seahawks’ mascot is named Blitz. Is he a Nazi? What about Chicago’s former USFL team, the Chicago Blitz?
Alluding to a Trump Truth Social post, Stewart continued as he introduced his guest, “They'll find out why it's called the Department of War, and by the way, I don't believe that's Wins Above Replacement. But we are fortunate enough today to be speaking with the field general who is tasked with repulsing this military incursion, and that is the governor of the great state of Illinois. He is joining us now from the front lines. Let's go to him now. Governor JB Pritzker. So, ladies and gentlemen, we are obviously, we have a correspondent in the war zone that is now Illinois. It is Governor JB Pritzker. Sir, welcome to the show.”
Stewart then wondered, “Operation Midway Blitz, is it underway in Chicago? Has Chicago fallen? What, what is this? What the hell is happening?”
Pritzker began by lamenting, “Well, reporting to you from the front lines, ICE is on the ground. We have already seen some arrests. They are not in full force yet. We've only seen, well, less than 10, detainments, arrests, but they are, they only have, it seems like a dozen or two dozen people so far. We know they have as many as 300 agents that have landed at the naval station at Great Lakes and they are—”
Despite the fact the military is not actually on the ground in Chicago, Stewart continued with the World War II theme, “Did they take watercraft and do a water landing and then storm the beach?”
Pritzker reiterated that, so far, only ICE is involved but warned the administration wants a pretext to send the troops in, “They have come with 100 vehicles. They are unmarked vehicles, and we know that they are preparing to span all of Chicago, and indeed some of the arrests that occurred yesterday were in suburbs of Chicago. So, it's a pretty widespread endeavor, and it's being led by Gregory Bovino, who led the ICE raids in Los Angeles and caused all of that mayhem on the ground. That's their intention here, but to do it, you know, even more so here because Donald Trump wants to create a situation for Chicago where he can bring in the National Guard.”
For a man who is constantly freaking out about Trump cancelling elections, Pritzker sure has been doing a lot of interviews recently to get his name recognition up for 2028. Maybe eventually an interviewer can point out the flaw in arguing that ICE “caused all of that mayhem.” ICE didn’t cause that; the rioters used their free will to engage in lawlessness. In the meantime, recent developments should lead Stewart to quit trivializing Nazi crimes by comparing them to standard law enforcement operations.
Here is a transcript for the September 10-taped show:
Comedy Central The Weekly Show
9/11/2025
JON STEWART: It is, we're taping this on Wednesday, September 10th, it's gonna be airing tomorrow, and today is the day they launched Operation Midway Blitz. Named for the city of Chicago and what the Nazis did through Europe. What could go wrong? They'll find out why it's called the Department of War, and by the way, I don't believe that's Wins Above Replacement. But we are fortunate enough today to be speaking with the field general who is tasked with repulsing this military incursion, and that is the governor of the great state of Illinois. He is joining us now from the front lines. Let's go to him now. Governor JB Pritzker. So, ladies and gentlemen, we are obviously, we have a correspondent in the war zone that is now Illinois. It is Governor JB Pritzker. Sir, welcome to the show.
Operation Midway Blitz, is it underway in Chicago? Has Chicago fallen? What, what is this? What the hell is happening?
JB PRITZKER: Well, reporting to you from the front lines, ICE is on the ground. We have already seen some arrests. They are not in full force yet. We've only seen, well, less than 10, detainments, arrests, but they are, they only have, it seems like a dozen or two dozen people so far. We know they have as many as 300 agents that have landed at the naval station at Great Lakes and they are—
STEWART: Did they take watercraft and do a water landing and then storm the beach?
PRITZKER: They have come with 100 vehicles. They are unmarked vehicles, and we know that they are preparing to span all of Chicago, and indeed some of the arrests that occurred yesterday were in suburbs of Chicago. So, it's a pretty widespread endeavor, and it's being led by Gregory Bovino, who led the ICE raids in Los Angeles and caused all of that mayhem on the ground.
STEWART: Right.
PRITZKER: That's their intention here, but to do it, you know, even more so here because Donald Trump wants to create a situation for Chicago where he can bring in the National Guard.