Paul Krugman in Conversation with (military historian) Phillips O'Brien

TRANSCRIPT:
Paul Krugman in Conversation with Phillips O’Brien

(recorded 8/20/25)

Paul Krugman: Hi everyone. Paul Krugman again. I'm speaking for a second time with Phillips O'Brien, a military historian. He's had a lot of influence on how I think about history even before Ukraine. His book, How the War Was Won, completely changed how I thought about World War II. He’s often contrarian but almost always right in his comments since this whole Ukraine thing started. And I thought that after this past week with Alaska and then the gang of Europeans coming to DC, it would be a good time to check in again. So hi, Phillips.

Phillips O’Brien: Hi Paul.

Krugman: I want to get to your new book towards the end and I want to talk about the diplomacy or whatever it was that we just saw in Washington shortly, but first I'd like to talk a little bit about the war in Ukraine.

O’Brien: Okay.

Krugman: You recently wrote that we have the worst military analysis community in the history of military analysis communities. And I want to talk about that a bit because I think I have some notion of what you mean.

O’Brien: Yeah. They just don't know how to judge war. Never have. This is the same group of analysts that said Kiev would fall in three days and Russia is a great power and the war would be quick and fast. And now they seem to be watching and obsessing about every little—not even village—almost every little farm field in the Donbas, and impregnating all of these tiny little Russian advances or failures to advance as some part of the indication of an impending Ukrainian collapse or anything in the like. They just don't understand, I think, how to judge a war and what really matters.

Now, the battlefield is what the battlefield is. I mean, it's one of those things where, technologically, they were wrong. The analysts were all telling us how tanks were going to rule the battlefield early in the war. They didn't understand that. So they thought, “Drones? Who cares about drones?” They simply, I think, have an old paradigm, like, the battle-centric paradigm, where literally, if Russia takes a farm field, that indicates something. But it never really does. I mean, we have seen the same basic war for two years now. The Russians have made very small, very bloody advances for 1% of Ukraine. Now, Ukraine isn't turning the tide of the war with that, but it's not about to collapse. I think that's the problem in their analysis.

But actually, the real part of the war that I think people have to pay much more attention to is what we'll call the strategic air war. The war in some ways is going to turn a lot on the strategic air war.

Continued. Also video is available
https://open.substack.com/pub/paulkrugman/p/talking-with-phillips-obrien