00:00 – John Sipher
All right. Today’s guest is Phillips O’Brien. He’s one of the sharpest contemporary writers on war, strategy, and political power. He’s a professor of strategic studies at the University of St. Andrews and the author of several major books, including How the War Was Won, The Strategists, and The Second Most Powerful Man in the World. He also writes regularly for The Atlantic, Foreign Affairs, and has his own excellent Substack, Phillips’ Newsletter.
His most recent book, War and Power: Who Wins Wars and Why, argues that battles rarely determine outcomes. Instead, they reveal the underlying strengths and weaknesses of the states fighting them. That framework should help put in perspective our discussion today on the U.S. strikes on Iran, Ukraine’s deep strikes into Russia, Europe’s growing responsibility for Ukraine’s survival, weaknesses in American strategy, and the way authoritarian leaders try to sell battlefield failure as political strength.
So welcome, good to have you.
01:26 – Phil O’Brien
John, it’s delightful to be here.
01:28 – John Sipher
We’re also good friends and have a regular Signal channel with a number of other people where we complain about the day’s events.
01:36 – Phil O’Brien
And occasionally we have a beer together in Scotland. But yeah.
01:38 – John Sipher
Yeah, it’s a little hot here, so I’d like to be in Scotland right now.
01:43 – Phil O’Brien
I got my fleece on. So, you know, everyone else has a heat wave. Scotland is like, “Whoa, it’s a little bit cool today.”
01:50 – John Sipher
All right, well let’s go. And since you’re a historian, some of these things that are happening today – we’ll try to figure out what might be the bigger impact politically and historically on these things. Your most recent book argues that battles don’t decide wars, but they do reveal the character of the states fighting them. What did the Iran War reveal about the United States?
02:12 – Phil O’Brien
Jesus, nothing good. No, no, really. I mean, it’s deeply depressing to me to see what’s happened. It revealed a number of things.
One, that the government is strategically incoherent. It had no idea why it went to war, what it wanted to achieve, and how it expected to use military force to achieve national goals. None of that was there. It just seemed to be – they went to war because Trump thought he could go to war and have a victory. So it showed the profound strategic incoherence at the top of the U.S. government.
But that in some ways was not a surprise because that’s the way Trump is. There is a strategic incoherence to him. So it simply revealed a very problematic thing about him.
The more depressing thing to me is how it revealed that the U.S. military is showing signs of degradation already. And this is something I think we have to face. The phrase is “a fish rots from the head down.” Well, the head is rotting. And that is, I think, translating down to the military.
My guess is it’s a combination of weaker officers getting promoted, people cutting corners, not receiving direction, people with good ideas and open minds not able to advance in their careers. And we saw a military that wasn’t prepared, didn’t have certain technologies available to it – cheap technologies to defend itself against drones – which seemed to have trouble executing a lot of its missions. And it didn’t perform in the way that we would expect the U.S. military to perform.
04:04 – John Sipher
I’m reading the Haberman and Swan book now, Regime Change. I’m just at the point where they’re talking about the original strikes on the nuclear program – before the larger war. It’s amazing to read. Essentially Trump thought he was still involved in negotiations, claimed he didn’t want to be part of the Israeli attack, and just continued watching until literally one day he saw that Israel was having success and said, “We need to be part of it. We need to claim we were behind this.” Then he essentially went to the Pentagon and said, “Start striking now.” And they had to respond.
As you know, as a historian of the military, the military is all about planning and preparing and putting together options. If you tell someone to attack a country and expect them to do it 15 minutes later, you can’t really expect great success in the sense that technically it worked out okay. It’s almost a surprise given the leadership problems.
05:05 – Phil O’Brien
Yeah. The strikes in February – they didn’t happen overnight. They had been building up to them for a while. And still I would argue they suffered from significant logistical problems in the way they put it together. They blew through stockpiles. It just didn’t seem to be well planned when given time.
My guess is that speaking your mind in the Pentagon and being critical is now not accepted. People can’t say “we’ve got a problem here” or “the head doesn’t know what it’s doing” because the head will lash out at you if you do that. I don’t see how we get out of it for the next few years. My worry is it gets worse.
05:55 – John Sipher
Politics can operate in the unreal, but military, intelligence, and diplomats have to operate in the real world. I know at one point you wrote some detailed analysis about the memorandum of understanding between Iran and the United States. Walk us through that a little bit. What do you think that tells us about American power and our concessions?
06:18 – Phil O’Brien
Trump got nothing. That’s the whole thing. You read the memorandum of understanding, and Iran is in a better shape at the end of that than it was on February 27, 2026, before the bombing started. Because it’s got tacit things that were never on the table before. Tacit acceptance of Iran’s control of the Strait. The agreement does not rule out Iran charging tolls. It almost accepts the fact that Iran has this ability to charge tolls. It does say the sanctions on Iran are going to end. It talks about a $300 billion rebuilding fund for Iran. It talks about basically protecting Hezbollah in Lebanon – it’s trying to say there are certain things that cannot happen.
Iran comes out of this with significant strategic goals being met. I do not know what the United States gets that it didn’t have on February 27. That’s what I don’t understand. And no one’s been able to give me an answer.
07:20 – John Sipher
Yeah, I don’t see it either. It also surprises me that right away the things Iran asked for involved Lebanon. It wasn’t even part of the war, and we gave into it. Israel’s got to be crazed over what the administration is doing without consulting them.
07:41 – Phil O’Brien
Israel made the deal with the devil. Netanyahu failed to accept the truth that Trump will never be loyal to anyone but Vladimir Putin. The only thing Trump is loyal to is Putin. He’s not going to be loyal to Israel, he’s not going to be loyal to any state. He sold the Israelis out when he thought it was the best time for him – as he was always going to do. The funny thing is that people still trust him. I think at this point the United States is utterly untrustworthy. Europeans now know that. States like Japan, South Korea, Taiwan know that. Everyone’s going to be polite, but no one’s going to trust the U.S.
08:29 – John Sipher
You wrote a great piece in The Atlantic talking about a hypothetical U.S.-China war. In fact, it’s one of the bleakest things you’ve published – amongst other bleak things. It suggests the U.S. is currently positioned to lose a war with China. What is our weakest link? Industrial capacity? Military planning? Alliance structure? Political will? What bugs you the most?
09:02 – Phil O’Brien
All those things. But let’s start with the basic thing: wars are not won by the forces you have when they start. That’s the great problem with studying wars. Everyone thinks wars will be won by the forces you have when you start. That’s why Russia was going to conquer Ukraine in three days. That’s why the U.S. was going to win the war on terror in 2001. Wars don’t work like that. They go on longer than you think. They show adaptation and evolution.
The problem the U.S. has is it manufactures what – ten percent of what China does? If you’re looking at raw manufacturing capacity, they’re completely out of whack. The U.S. has no shipbuilding industry to speak of now. It’s entirely gone. So even if the U.S. wins the opening battles – and I’m not sure now they would – it doesn’t matter because they can’t make up anything they lose.
The United States is running out of weapons fighting the Iranians who cannot shoot back in most cases. They’re bleeding Tomahawk stockpiles, Patriot stockpiles, F-16 stockpiles. How do they expect to fight the Chinese? I think it’s got to the point that the United States wouldn’t even try to fight for Taiwan now. Where are they going to fight from? How are they going to do logistics across the Pacific? The U.S. is almost out of the game.
Which, by the way, Trump’s probably not unhappy with because he likes President Xi a lot and he couldn’t care less about Taiwan. But I wouldn’t want to see that war for the U.S.
10:44 – John Sipher
Reading that book, it’s clear he doesn’t care about much of anything except himself. He doesn’t care about Taiwan, but he is aware of the chipmaking capability in Taiwan and how that would affect the economy.
Give me a bit of a rant on Hegseth. His view is that it’s about hand‑to‑hand combat and toughness and lethality – these are the keys to history and victory. As a World War II historian who talks about how wars are actually won, what is he getting wrong here?
11:20 – Phil O’Brien
Our great war leader couldn’t even stand, let alone do a push‑up. FDR couldn’t stand without a brace.
11:27 – John Sipher
It makes me feel better because I watch his workout videos and I’m a 65‑year‑old man. I’m like, I can lift more than that.
11:36 – Phil O’Brien
Hegseth’s whole military ideology – his whole military outlook – has already been shown to be wrong. He’s talking about things like the Russian military or the North Korean military – hyper‑macho militaries who do ultra‑aggressive charging maneuvers. And you know what? Those soldiers die. If you’re going to fight in the present environment like that, you’re going to die. You’re going to be killed by a drone. It’s not about hand‑to‑hand combat. The Russians and Ukrainians are not doing hand‑to‑hand combat now. You can’t live long enough on the battlefield to even see the enemy up close.
He’s talking about some sort of weird 300 – Leonidas and the Spartans – view of war that just doesn’t go on now. You need motivated, technologically advanced soldiers who are smart and willing to adapt to the technologies at hand. The key ones right now are the drone pilots.
12:30 – John Sipher
When I retired I worked for a while as a consultant with General McChrystal. He would tell stories about in Iraq when they got most successful – he led the SEALs, Delta Force, and Special Forces – they brought intelligence people in from NSA and CIA. The fighters at first were like, “Who are these guys? Fat people with nose rings? They have no place here.” But within a week they realized these were the people helping them win. Modern warfare is about brains more than brawn.
13:36 – Phil O’Brien
The Ukrainians are not infantry‑free now, but what they’ve understood is mass infantry is not how they fight. It’s small numbers of really motivated, trained soldiers who know what they’re doing. And they’re smart more than anything else because they’re really valuable. Replacing one of these people with ten unmotivated conscripts is going to be a disaster. Wars are going to go to the smarter side. That’s the side that wins.
14:37 – John Sipher
You’ve also written that Europe and Ukraine are starting to get their act together. What does that mean in practical terms? Is Europe finally becoming a strategic actor, or did they hang on to Trump for too long?
14:48 – Phil O’Brien
They definitely hung on to Trump for too long. 2025 was a disaster. Europeans really thought they could win Trump over. It was frustrating as an American living in Europe – “We’ll play golf with him, we’ll slap him on the back, we’ll tell him what a wonderful man. At some point he’ll realize how much we love him and how much better we are than Putin.” No, Trump will never do the right thing. He never does things to do the right thing.
Europeans wasted most of 2025 chasing this false dream of Trump.
Finally, he did push them too far. Greenland was a great moment – January 2026 really mattered. The Europeans thought the Americans might actually invade. Trump didn’t reassure them. He made it look like it was possible. From that point on there’s been a real change in Europe, reinforced by the war against Iran – because that war affected Europe much more than the U.S. economically, and Europeans weren’t consulted, they weren’t in the room, their needs weren’t taken into consideration. They were simply told, “Deal with it – this is a U.S. decision and we are the great power.”
If that’s what you see from your “closest ally,” you realize it’s not your closest ally anymore. They’ve basically decided Ukraine’s victory or success – there’s not a consensus in Europe about what Ukraine’s victory should look like, but Ukraine’s future is more widely understood as important to them. They have replaced the United States as the big benefactor of Ukraine.
Also, the Ukrainians fought back so effectively that the Europeans realized they had miscalculated. In 2025, Europeans were not optimistic about Ukraine. They really thought Ukraine was going to have to take a bad deal. Then in 2026, all of a sudden the Ukrainians are doing impressive stuff. The Ukrainians saved Europe in a way – or certainly gave it breathing space to make the mistakes of 2025 that are hopefully now over.
17:59 – John Sipher
What are they doing? Are they increasing capability? Do they really have the ability to fight? Obviously part of the problem is a lot of these places invested in the U.S. So when it came to building their own forces, they were only putting together pieces that supplemented what the U.S. was good at. Now they’re going to have to build across the board. Tell us a little bit about who gets it, what they’re doing, and what capabilities exist right now or in the near term.
18:31 – Phil O’Brien
That’s such a great question. In many ways, no one fully gets it. But what they’ve been able to do is parts of the different militaries – the German, French, Scandinavian, British – are cooperating with the Ukrainians on things like drones, often because they don’t have a drone industry themselves. So they’re learning from the Ukrainians as well as bankrolling. There’s almost a symbiotic relationship now between Europe and Ukraine when it comes to militarization.
But they did waste time. Throughout 2025, they didn’t push ahead with their own anti‑air systems – they were just trying to scavenge Patriots from around the world. Europe can make its own anti‑air systems. It has the technologies. They just sat on their ass and didn’t do it because they had access to Patriots. Now they’re thinking about European versions of anti‑air systems, more advanced ones.
They’ve also provided cash to Ukraine, which is really important because the Ukrainian war industry is now a vital asset. Ukraine can make up to seven million drones this year – an amazing figure for a country that didn’t make a drone in 2021. So providing money to that is a huge part of European defense.
20:10 – John Sipher
As a quick aside, what’s happened recently with the friction between Ukraine and Poland? What’s that about?
20:19 – Phil O’Brien
This is one of the most horrible stories. In some ways, the Ukrainians might have been politically more sensitive. They named a new military unit after a Ukrainian nationalist military force from World War II that the Poles believe committed atrocities against Polish forces. The Russians will say it was pro‑Nazi, the Poles will say it was anti‑Pole, and the Ukrainians say it was the Ukrainian nationalist movement oppressed by both the Russians and the Poles.
There’s a lot of history here, and maybe the Ukrainians should not have named the unit that. But the Polish president – who is sort of a MAGA guy – turned around and said, “No, you can’t name this unit. That’s an insult to Poland. We’re stripping Zelensky of an award.” He’s striking out at Ukraine in a real way.
Whatever you think of the Polish‑Ukrainian historical argument, Ukraine is fighting for its life and defending Poland right now. This dispute does not help anyone but Putin.
22:02 – John Sipher
Is this mostly the president and his party, or is it wider Polish anger at Ukraine?
22:09 – Phil O’Brien
There was some Polish disquiet on all parties. But Donald Tusk, the Prime Minister, is a different party than the President. The President is more of a MAGA version of Poland, and it seems to be him driving this. Radek Sikorsky, the foreign secretary of Poland, tried to calm the dispute. But it’s gotten to the point where the Ukrainians are saying, “We’re going to name our units after who we want.” Budanov said no holds barred. Zelensky says the same. I don’t see how this helps anyone but Putin.
23:12 – John Sipher
And it gives the Russians something to amplify.
23:16 – Phil O’Brien
I know I’m going to get angry letters from Poles for saying that. But I can’t see how this helps anyone but Putin, and I don’t see how helping Putin helps Poland.
23:27 – John Sipher
Let me go back. You called Biden’s Ukraine policy a catastrophic failure. What was the biggest mistake?
23:41 – Phil O’Brien
The Biden administration’s view was that they could manage this war – what I call a Goldilocks strategy. Not too hot, not too cold. They wanted Ukraine to survive – that’s in their credit. Trump couldn’t care less about Ukraine. But on the other hand, they didn’t want Russia to lose. They didn’t want a catastrophic Russian defeat or instability. They tried to control the war so Ukraine wouldn’t fail but Russia wouldn’t lose.
They thought they could micromanage the war – “We’ll fight on the front lines, we won’t let Ukraine strike into Russia.” It ended up being a catastrophic failure because Ukraine could have won in 2022 had it been properly armed. Every weapon the Biden administration first said Ukraine didn’t need – they needed. Patriots, F‑16s, HIMARS – they got them too late. Then Trump comes to office and just ends all aid. The tragedy is the Biden administration sort of got it by the end of 2024, but by the time they got it, they left office and we went to the pro‑Putin administration.
25:28 – John Sipher
This is an American problem. We’re so large and powerful that we think we can choreograph the perfect outcome – “We don’t want Putin to fall because that could be a mess, so let’s beat him but make sure he doesn’t really lose.” We’ve done this with all kinds of wars. In Afghanistan, “We don’t want to mess with Pakistan but we want to go after the Taliban.” We play this game like you’re trying to choreograph something you actually can’t control.
26:08 – Phil O’Brien
Let me ask you – from your outsider perspective, it seemed the Russian analysis coming out of the IC was very Moscow‑centric. It was based on this idea that “we need to work with Moscow, we don’t want Russian failure.” It was almost sympathetic to the subject it studied. Is that unfair?
26:43 – John Sipher
No. The older you become what you study, right? A lot of people who are experts came up through university courses taught by the old White Russians, then the next generation, part of the larger Cold War superpower study – Russia‑centric. I think it’s going to be the next generation of academics who give other countries their due. The analytic community was way too Russia‑centric in how it sees things. It’s much easier to deal with Russia and solve all your problems.
On the collector side – the operator in the field – we were much more skeptical of Russia. You need to punch Russia in the nose. Everything is part of their warfare – negotiation is part of warfare. Our analytic community seems to be different. I think this war has taken the blinders off a lot of those people.
28:15 – Phil O’Brien
It’s all whether we can rebuild after this administration too. Do you have to clean house completely when this is over?
28:26 – John Sipher
Certainly in some places you do – Justice Department, maybe the FBI. I tend to think intelligence agencies are a little harder for outsiders to figure out and deal with. But you’ve got two and a half more years and there are some crazy people in there. We’ll see.
28:55 – John Sipher
You said you struggle to think of a midterm election as consequential as this one in 2026 – except maybe 1862. Why that comparison?
29:02 – Phil O’Brien
1862 is the midterm during the Civil War. Had the Democrats won, you might have had a treaty between the North and South that would have given the South independence. It was vitally important that the Republicans win to support Lincoln’s policies. The country’s future would have been materially different had the Democrats won. That’s the only one I can think of comparable to this midterm.
The fundamental problem: Trump is strategically incoherent, he’s a strategic moron. He’s a political genius, by the way – I hate to say that – but a strategic moron. The big problem is he’s corrupt as hell. The United States is now a corrupt government.
30:12 – John Sipher
I hope people run on corruption and incompetence, because those are the fundamental things behind all the issues we see.
30:22 – Phil O’Brien
If you can’t root that corruption out soon, it’s going to embed itself. It’s already embedding itself now. If the Republicans win the 2026 midterms, who knows what they’ll do legally to keep power – to protect corruption? Speaker Johnson said the other day, “You don’t want to vote Democrat – they’ll investigate the Trumps.” They’re actually protecting this.
30:52 – John Sipher
As a clandestine collector overseas, one thing that allowed us to be successful was that the countries we often worked in were corrupt and incompetent. And the people there realized they couldn’t change the system and wanted to work with the United States – who they saw as something different. If we’re just another corrupt, grab‑as‑much‑as‑you‑can place, we’re going to lose something special.
31:40 – Phil O’Brien
We are that now. Right now we are a grab‑as‑much‑as‑you‑can government. I can’t see anyone who’s not out to grab. This is my worry. How do you get back from it? You end it as soon as possible because once systems go corrupt, it becomes entrenched.
32:08 – John Sipher
Can you articulate what MAGA means to the U.S. place in the world? What was the world order we had? How is it changing? What are we losing? A lot of Americans focus on day‑to‑day – “I want my gas cheaper.” Those of us who worked for the government saw this world order as beneficial to us. Why was it important?
32:49 – Phil O’Brien
One element of American power that people underrated was the value of allies. The United States was in charge of more than half of the world’s economy through its allies. That’s why it was this great global power. If the United States now has no allies – that’s what MAGA is saying. If you read the National Defense Strategy, it’s basically saying “We’re Western hemisphere focused – our allies are a problem.”
The United States is going to wake up in a few years and realize it has lost its alliances entirely by choice. The United States chose under no pressure to give up an alliance system that made it strong. It doesn’t feel it now because people care about the price of gas. What they don’t realize is the stability we had for 80 years was because of the U.S. alliance system. Without that, the world is going to be far more unstable – and the United States chose to end it.
34:40 – John Sipher
Are we watching a true revolution in warfare – drones and the way they’re fighting – or is this simply the latest version of an old pattern where you find new ways to do something, the tank comes along, then you have to create something to counter it?
35:04 – Phil O’Brien
We are witnessing something really important: the swing away from the highly advanced, exquisite piece of military equipment – F‑35s, aircraft carriers, small numbers of hyper‑advanced machines. What we see in Ukraine is that the exquisite has a real problem. You don’t need the exquisite if it can be matched by massive cheap systems. Something like an expensive battle tank – what’s the point when you can have drones that cost $200‑300 that represent a threat to it?
The real change is the growth of cheap mass systems that threaten large, exquisite, expensive systems. That’s not just the Russians – that’s also the U.S.
36:22 – John Sipher
Does that mean something for large, powerful countries? Does it make us less powerful? We’ve essentially lost most of the wars we’ve fought recently. Is the ability of big powers to get their way militarily at some point going to be a thing of the past?
36:49 – Phil O’Brien
The Russians are not getting their way in Ukraine, and the United States did not get its way in Iran. The best Chinese choice for a while was to sit back and let the Americans make the mistakes. I think we’re learning the limitations of military power. My real worry is this Pentagon – led by this Secretary of Defense and this president – cannot be the ones to modernize the U.S. military and adjust to this world. They are simply not capable of doing it. If they get an extra $500 billion, it’s just going to make things worse because it’s going to be money thrown at morons.
37:38 – John Sipher
Do you think the Chinese are getting the memo? Are they saying “big powers using military to get their way doesn’t work”? Or are they convinced Taiwan is so important they’ll be able to do it?
37:57 – Phil O’Brien
I don’t know. The Chinese military is probably making a lot of stupid decisions too – Xi is purging the Chinese military right and left. One worrying sign: the Chinese seem less focused on an invasion of Taiwan – which would be a catastrophe for them – and more towards a blockade strategy. That’s a real problem for Taiwan and for the U.S. If that’s true, it’s a sign they’re learning and adjusting to this world. Worryingly so.
38:49 – John Sipher
Authoritarian systems often survive defeats by renaming them victories. Putin does it. Saddam did it. Trump seems to be doing that now. What’s the downside – the long‑term damage – when you try to control history and the narrative?
39:15 – Phil O’Brien
The one positive thing is he hasn’t seemed to be able to do that for most Americans. He has his base – they will believe anything he says. “I’ve beaten Iran, humiliated Iran, crushed Iran” – 30% of America will say yes. But more Americans don’t seem persuaded. Polls show most Americans believe the war had no point and achieved little. If we see more and more Americans accepting the idea they did well in this war, that’s a worry. That means Trump is winning the narrative fight – and that’s the only fight that matters to him now. He just wants out. So far he’s not winning that debate – that’s positive. If he does, it’s really worrying.
40:23 – John Sipher
The real pain of what we did in Iran was felt outside the United States. Yes, gas went up some, there’s some inflation. But there are countries where they had to go from five‑day work weeks to three‑day work weeks – real pain and suffering. In the past, when the U.S. made strategic blunders, people said, “It’s better to have America leading than not leading, even if we’re upset.” Now we’re causing the world such pain and look so corrupt that we’re not going to get our way like we did in the past.
41:16 – Phil O’Brien
The Europeans basically think the U.S. started a war to harm Europe and didn’t care about Europe. The Gulf states who fought side by side with the U.S. in this war no longer believe in the United States. The arc of American friends and allies – no one is convinced the U.S. is a reliable partner on whom they should base their future security. The Gulf states are now reaching out to Iran. We have improved Iran’s position because the United States seems so poor at running this war.
42:07 – John Sipher
Is there any hope, any optimism here?
42:11 – Phil O’Brien
The midterm elections. We’ll see whether the American people really want to change. Europe and Japan are waking up – if the United States ever regains its senses, there will be better partners for the United States, more powerful partners willing to look after themselves. That means the United States could have stronger partners going forward than it had before.
42:48 – John Sipher
Maybe this is one of those big turning points in history. Trump got us there in the wrong way and earlier than we wanted.
43:04 – Phil O’Brien
It didn’t have to be quite this dramatic.
43:16 – John Sipher
You’ve been generous with your time. I would suggest people follow Phillips – his Substack is fantastic. When you see his byline in The Atlantic or hear him on NPR, you should pay attention. What’s your next book?
43:24 – Phil O’Brien
I’m working on a new one – not entirely signed and sealed – but I’m most interested in the history of military logistics, from the classical period all the way to Russia‑Ukraine and even China‑Taiwan. A study of historical military logistics.
43:52 – John Sipher
What’s the thesis?
43:52 – Phil O’Brien
Everyone says “amateurs discuss tactics, experts discuss logistics.” If that’s true, it’s interesting there are hardly any experts in the historical profession because nobody writes about logistics. It’s a way to say this is how logistics work and why they matter.
44:11 – John Sipher
Outstanding. When that comes out, I will read it. Phil O’Brien, thank you so much for your time. For people, this has been the Steady State Sentinel. If you like what you’re hearing, please subscribe to the Sentinel and follow Steady State content. If you can give us a review, that would be great – they help us get the content to a wider audience. Thank you very much, everybody, and thank you to you, Phillips.
44:38 – Phil O’Brien
Take care, John.